Farmaceutical Chemistry

. . , . . , . .
,
. . , . . , . . ,
. . , . . , . . ,
. . , . . , . . ,
. . , . . , . . ,
. .

IIIIV

..

2002
615.014(075)
35.66/1
24

( 23-01-25/501 26 2001 )
:
. . , , ,
;
. . , , , .
: . . . . .
24 . . . - . . . . IIIIV
/. . , . ., . . .;
. . . . . .: - ; , 2002. 448 .
ISBN 966-615-082-4.
ISBN 966-95981-2-5.
,
,
.

.
.
615.014(075)
35.66/1
ISBN 966-615-082-4
ISBN 966-95981-2-5
.., .., ..,

.., .., ..,
.., .., ..,
.., .., ..,
.., .., ..,
.., 2001
, 2001
IIIIV
.
,
.

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1866 . . XI .
.
244
19.03.97 . . , . 1998
, . () , .
95 12.03.2001 .
01.10.2001 .
,
, (), .
. , , ,
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XI ,
,
. (GMP).
. .
6

,
. () : (
) , N, ( , ).
,
( ) ,
, GMP. , , XI , , , .
.

, .
, GMP,
.

.
, , ,
, . .
. , . ,
, ,
. . .
:
1. ( , ,
).
2. . :
2.1. (;
).
2.2. - , . 7
N ( , ).
2.3. ( ).
, , , .
:
) ( (V)) :
Na+ + K[Sb(OH)6] 89 Na[Sb(OH)6]5 + K+
) :
OCH3
+
Na + C6H5CHCOO[N(CH3)4] 89
OCH3
+
89 C6H5CHCOONa# + N(CH3)4

.
:
)
,
:
OH
Ca2+ +
HO
N=CHCH=N
O
89
89
Ca
N=CHCH=N
O
+ 2H+
) (II) .
:
Ca2+ + 2NH4+ + K4[Fe(CN)6] 89 (NH4)2Ca[Fe(CN)6]5 + 4K+
8

, :
Al3+ + 3NaOH 89 Al(OH)35 + 3Na+
5Al(OH)3 + 3NaOH 89 Na3[Al(OH)6]
:
Na3[Al(OH)6] + 3NH4Cl 89 Al(OH)35 + 3NH4OH + 3NaCl
:
)
:
Pb2+ + K2CrO4 89 PbCrO45 + 2K+

:
5PbCrO4 + 4NaOH 89 Na2[Pb(OH)4] + Na2CrO4
)
:
Pb2+ + 2KI 89 PbI25 + 2K+
,
.
(III)
:
Fe3+ + 3KSCN 89 [Fe(SCN)3] + 3K+
.

.
(II) :
2[Fe(SCN)3] + 3HgCl2 89 3[Hg(SCN)2] + 2FeCl3
- ;
- :
6I + K2Cr2O7 + 7H2SO4 89
89 3I2 + Cr2(SO4)3 + K2SO4 + 7H2O + 3SO42
9
(III, V) :
NaH2PO2 + HCl 89 H3PO2 + NaCl
As2O3 + 3H3PO2 89 2As5 + 3H3PO3
As2O5 + 5H3PO2 89 2As5 + 5H3PO3
- ,
, - .
:
4Cl + K2Cr2O7 + 3H2SO4 89
89 2CrO2Cl26 + K2SO4 + 3H2O + 2SO42

:
NHNHC6H5
O=C
CrO 2Cl2
NHNHC6H5
O=C
NHNHC6H5
N=NC6H5

Cr2+, - :
NNHC6H5
Cr2+
+ COH
NNHC6H5
+ 2H+
12 COCr
N=NC6H5
N===NC6 H5
- - :
PO43 + HVO3 + 11H2MoO4 + 4NH4+ 12
12 (NH4)4[PO4(MoO3)11VO3] + 11H2O + H+
-
,
:
CH3COO +
COOH
COOH
89 CH3COOH6 +
10
COO
COOH
2.4. . ,
XI, . :
. , (II) ( ). , , 40 .
MgO + H2O 89 Mg(OH)2
2NH4+ + Mg(OH)2 89 2NH36 + 2H2O + Mg2+
2AgNO3 + MnSO4 + 4NH3 + 2H2O 89
89 2Ag5 + MnO25 + (NH4)2SO4 + 2NH4NO3
. , ,
,
.
. I, XI, ,
,
:
2AsH3 + 3HgBr2 89 As2Hg3 + 6HBr
. .
, , .
.
, ,
:
SiO2 + 6HF 89 H2[SiF6]6 + 2H2O
H2[SiF6] + 2NaOH 89 Na2[SiF6] + 2H2O
OH
CH2CO
CH2N
O
OH2
Ce
CH2CO

O
11
OH2
Na2[SiF 6]
NaOH
ONa
ONa
CH2CO F
89
CH2N
O
OH2
Ce
CH2CO
OH2
. 8-
:
2
+ Mg2+ 89
OH
N
O
+ 2H+
N
Mg
.

- , , :
CH3C
S
NH2
+ 2H2O + Pb2+ 89 PbS5 + CH3COONH4 + 2H+
. (II)
:
PO43 + 12(NH4)2MoO4 + 27H+ 89
89 H7[P(Mo2O7)6] + 24NH4+ + 10H2O
- , Sn2+ .
.

:
K+ + NaB(C6H5)4 89 KB(C6H5)45 + Na+
12
. 8-
:
3
+ Al3+ 89
Al
OH
+ 3H+
N
O
2.5. . :
, , , . .
2.6.
.
2.7. . .
2.9. - .
4. . ,
,
, ,
, .
5. . , , N.

100 .
.

N.
,
.
() /
(),
.
,
13
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( ), .
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:
1.
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13.
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18. (,
, . .)*.
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.)*.
20.
.
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*.
*.
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()*.

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: ; ; (), .
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14
23. *.
24. (
).
25. * ( )*.
26. .
27. *.
28.
29.
30.
31.
32.
33.
.
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,
IUPAC, - (
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(, ) .
- .
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15
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.

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2. , ,
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.

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a) ;
) ;
) .
, ,
, .
16
, (III) : NH4SCN, 4[Fe(CN)6],

.
O
H
CC
HO3S
S
OH
COOH
OH
(III) , ,
(III),
.

. ,
, .
.
. ,
, .
,

.

, .
, , .
, ,
,
() ( , , 0,02 %).
, ,
( ), , , .

. , , , : -,
-, , (II), (III), ,
, , (III), (V) ,
. 17
, , . .
,

1. , .
2. , ,
.
3. 0,001 .
4. .
5. ,
, .
6. .
7. , ()
, (), . , , (,
).
,
( ), , . .

:
Cl+Ag+89AgCl5

. ,
5 .
,
, 18
g2CO3 ,
AgOH, Ag2O. ,
( Ag2SO4, Ag3PO4),
, .
:
5AgCl + 2NH4OH 89 [Ag(NH3)2]Cl + 2H2O
:
[Ag(NH3)2]+ + Cl + 2H+ 89 AgCl5 + 2NH4+

:
Ba2+ + SO42 89 BaSO45
, .
,
, I (-, -,
-). , ,
. , () , .

I. ( ):
NH3 + 2K2[HgI4] + KOH 89
IHg
IHg
NH2 I
+ 5KI + H2O
, .
, , 19
, , ,
( Fe3+),
- :
O 0C 8C H 8C H8C
O
Fe
II. , .
NH4++OH
NH36+H2O

,
:
Ca2+ + C2O42 89 CaC2O45
5CaC2O4 + 2HCl 89 CaCl2 + H2C2O4

.

-
- , :
[Fe(COO)2(O)2(C6H3SO3)2]3
= 812 ( ).
, , .

.
20
,
,
,

:
Al(OH)3 + NaOH + 2H2O 89 Na[Al(OH)4(H2O)2]

. , ,

.

( ) :
3Zn2+ + 2K+ + 2[Fe(CN)6]4 89 K2Zn3[Fe(CN)6]2 5
, , .
(III), .
(III) ,
.

.
(II) .
:
Pb2+ + S2 89 PbS 5
.

. , ,
.
21

I (III) ():
Zn 2e 89 Zn2+
As3+ + 6e 89 As3
As3 + 3H+ 89 AsH36
:
6Zn + As2O3 + 12HCl 89 2AsH36 + 3H2O + 6ZnCl2
,
:
AsH3 + HgCl2 89AsH2HgCl + HCl
AsH3 + 2HgCl2 89AsH(HgCl)2 + 2HCl
AsH3 + 3HgCl2 89As(HgCl)3 + 3HCl
AsH3 + As(HgCl)3 89As2Hg35 + 3HCl
0,0005 ,
. , ():
HgCl2 + 2KI 89 HgI25 + 2KCl
5HgI2 + 2KI 89 K2[HgI4]
- - (As2Hg3),
.
.
: I ,
; II .
.
( , ), . 1. ,
() , (II)
, .
, (IV) ( ),
Hg, HgS
22
.
.
40 ,
( ) 20 %.
II

.

, , , ,
, , , , .
NaH2PO2 + HCl 89 NaCl + H3PO2
As2O3 + 3H3PO2 89 2As5 + 3H3PO3
As2O5 + 5H3PO2 89 2As5 + 5H3PO3

. , 15 . ,
. . , .
II , I (
0,01 ).
, , I.

,
. , , ,
.
.
,
, P, , B9.
I. 2,0 , , 2,0
, ,

23
12 .
,
( ) .
II. 40- , , 40- ,
, ,
15 25 . ,
.

(III) .

.
(II) .

:
(10/),
B ()
3,0
3,0
2,4
1,6
BY (-)
2,4
1,0
0,4
6,2
Y ()
2,4
0,6
0,0
7,0
GY (-)
9,6
0,2
0,2
0,0
R ()
1,0
2,0
0,0
7,0
1 .

(10 /).
:
B (9 );
- BY (7 );
24
Y (7 );
- GY (7 );
R (7 ).
I
12 ,
. ,
II,
.
(B, BY,
Y, GY, R)13 I; (B, BY, Y, GY, R)49 II.
.

.

.

15 25 .
40- , ,
40- ,
.
5
.

, , , .
, , , .
I
II
III
IV
5,0
10,0
30,0
50,0
95,0
90,0
70,0
50,0
, ,
, I.
25
.
,
-, - ( ) .
I. () .

( ). ,
1 , 0,0005 . , , 100105 .
:
1) ;
2) ,
.
II. ( , ).
: (, , , ),
(
, ).
. .
III. .
, , ,
:
CaC2 + 2H2O 89 Ca(OH)2 + HC3CH6
IV. . , :
OH
O2N
N2
H 2O
O2N
N2
+
+ H3
N2
N2
, .
26
V. . ( ). , .
-
, . , .

:
SO2 + I2 + 2H2O 12 H2SO4 + 2HI
. , , , ,
:
3
+ I2 + SO2 + H2O 89
I +
+ CH3OH 89
O
O
CH3SO4
, , .
- .
pH
,
, ,
. .
.

, .
27
,
, - .
pH .

.
, pH 0,2 .
(23 ) . pH .
- () .
() , ( ) ,
. - . , ,
.

,
( : ,
, .).
,
. ,
,
.
, ,
, . ,
(
2 C). . .

. :
80 ;
80260 ,
, ;
28
260325 7 3
.

0,51 46 1 .

, ,
( ), .

,
.
.

, .

( 5 ) ( 95 % )
(101,3 760 . .). .

.
.
:
t1=t2+k(101,3 b),
t1 , C;
t2 ,
b, C;
b , ;
k (
).

: =m/V.
, ( , .) .
:
29
1. () 0,001.
=
(m2 m0 ) 0, 99703
(m1 m0 )
+ 0, 0012,
m0 ;
m1 ;
m2 , ;
0,0012 20 101,3 (760 . .);
0,99703 20 .
.
2. ( 0,01).
.
,
.
()

, .
( ):
n=
V1
V2
sin
sin
;
.
() , , .
.

:
n = n0 + C . F,
C =
n0
n
F
n n0
F
, %;
;
;
(
1 %).
30
20
D(589,3 ) . :
nD20 = 1,3330.
, :
n = n0 + n1 + n2 +...+ ni
n = n0 + C1F1 + C2F2 ++CiFi ,

:
C =
[(n n0 ) C1 F1 C 2 F2
F
... Ci Fi ]
.

.

()
. ,
(- , , .). ,
,
(+ d ); ( l ).
, 1 , () 1 1
().
20
D(589,3 ) .
:
[]20
D =
;
, /;
l ( ), .
31
:
[]20
D =
100
C l
C =
100
20
[]D l
, %.
.

,
. .

(II)
, .
,
:
CO2 + Ba(OH)2 89 BaCO35 + H2O
, :
CuSO4H2O + 4H2O 89 CuSO45H2O

, :
H2S + (CH3COO)2Pb 89PbS5 + 2CH3COOH

(, , - .).
32

:
1) ;
2)
. -, , (III)
:
3SCN + Fe3+ 89 Fe(SCN)3
3)
:
2NaCN + FeSO4 89Fe(CN)2 + Na2SO4
Fe(CN)2 + 4NaCN 89Na4[Fe(CN)6]
3Na4[Fe(CN)6] + 4FeCl3 89Fe4[Fe(CN)6]35 + 12NaCl
.

.
,
- :
Na2S+Na2[Fe(CN)5NO] 89Na4[Fe(CN)5NOS]

, .

, - (Cl, Br) (I) .
(
AgNO3).
.
, .
33
, .

1. .
, :
O
R8OH+R'C
O
H2O
OH
R'C
OR
2. :
RCH2OH
[O]
O
RC
[O]
RC
OH
, .

1. .

.
2. .
.
3. :
)
:
Br
OH + 3Br2 89 Br
OH + 3HBr
Br
) :
34
OH + HNO3
89
H O
2
OH 12
4.
- (NH3, NaNO2
.):
[O]
NH
OH 89 O
3
O 89
O
NH
OH
89 O
OH
5.
:
+
OH +
OH
N3N Cl 89 HO
N0N
.
, , - .
1. :
) :
O
RC
+ R'NH2
H2O
R8CH0N8R'
) ,
:
O
RC
+ R'NHNH2
H 2O
35
R8CH0N8NH8R'
2. -:
) ( ):
O
RC
+ 2[Ag(NH3)2]NO3 + H2O 89
89 2Ag5 + 2NH4NO3 + RCOONH4 + NH36
. ;
) ( ):
Cu2+ + 2OH 89 Cu(OH)25
COO
COONa
HCOH
HCOH
+ 5Cu(OH)2 89
2
HCOH
HCOH
COOK
COOK
2KNa[Cu(C4H4O6)2] + RC
O
H
2+
Cu
OOC
HOCH
+ NaOH + KOH
HOCH
NaOOC
+ 3NaOH + 2KOH 89
89 2CuOH5 + RCOONa + 4KNaC4H4O6 + 2H2O

2CuOH
Cu2O5 + H2O
. ;
) :
O
RC
+ K2[HgI4] + 3KOH 89 RC
O
OK
+ Hg5 + 4KI + 2H2O

.

1. (CuSO4, CoCl2, FeCl3 .)
.
2. (. ).
36
3. (
) :
RCOOH + NaHCO3 89 RCOONa + CO26 + H2O

1. :
O
RC
OR'
+ HOH89 R8COOH + R'OH
.
2.
,
(III) (II) :
O
RC
O
RC
FeCl!
NHOH
NH OH
RC
OR'
RC
O
NHOH
Fe /
NH8O
+ R'OH
RC
O
NH8O
Fe Cl
2

1. :
O
RC
NHR'
RC
ONa
+ NH2R'
, ,
.
2. ,
, -.

1. ( ):
37
ONa
NH2
NaNO2
N3N Cl
HCl
N
NaO
R
2. :
R
NH2 +
R'
O
C
89
H2 O
N0CH
R'
.

.
.

VI VII

VII (), VII ( ) VI
().

() HCl.
, 0,3 %.
(Acidum hydrochloricum)
(Acidum hydrochloricum dilutum)
HCl
.
, , ;

.
,
, , .
24,8
25,2 %, 1,1251,127 /3.

8,28,4 %, 1,0401,041 /3.
. :
, :
NaCl 89 Na+ + Cl
39
2Cl2e 89 2Cl
H2O+e=H0 + OH
H0+H0=H26
Cl0 + Cl0 = Cl26
:
2NaCl + 2H2O 89 Cl26 + H26 + 2NaOH
( ) :
H2 + Cl2 89 2HCl
HCl
,
3536 % ( ).
. 1. -:
HCl + AgNO3 89 AgCl5 + HNO3
:
5AgCl + 2NH4OH 89 [Ag(NH3)2]Cl + 2H2O
2.
, :
4HCl + MnO2 89 Cl26 + MnCl2 + 2H2O
. .
:
Cl2 + 2KI 89 I2 + 2KCl
1 .
() .
,
30 :
SO32+H2O+I2 89SO42+2HI
. 1. , ,
, = . .:
HCl+NaOH 89NaCl+H2O
2.
.
.
.
40
.
( ) .
, ,
,
.
.
() (Calcaria chlorata)
Ca
OCl
Cl
Ca(OH)2nH2O

.
. ,
.
:
CaO + H2O 89Ca(OH)2
Ca(OH)2 + Cl2 12CaOCl2 + H2O
.
. 1. 1:10
, (>7),
:
CaOCl2 + H2O 89Ca(OH)2 + Cl26
2.
( ):
Ca
OCl
Cl
+ 2HCl 89 Cl26 + CaCl2 + H2O

:
Cl2 + 2KI 89I2 + 2KCl
41
3.
,
:
2Ca
OCl
Cl
+ 2CH3COOH89(CH3COO)2Ca+Cl26+H2O+CaCl2
(CH3COO)2Ca + (NH4)2C2O4 89 CaC2O45 + 2CH3COONH4
. , , , = 1/2. .Cl2:
Ca
OCl
Cl
+ 2HCl + 2KI 89 I2 + 2KCl + CaCl2 + H2O

I2 + 2Na2S2O3 89 2NaI + Na2S4O6
32 %.
. , ,
.
. .

.

, .
(Natrii chloridum*) NaCl
(Kalii chloridum*) KCl
.
, . 3 ,
95 %- .
. 1. Na+:
) ;
)
-
:
*
42
Na+ + Zn[(UO2)3(CH3COO)8] + CH3COO + 9H2O89

89NaZn[(UO2)3(CH3COO)9]9H2O5
2. K+:
)
-;
) ()
,
:
COOH
HC8OH
HC8OH
COOK
+ KCl 89
COOH
HC8OH
HC8OH
+ HCl
COOH
) ( ) :
Na3[Co(NO2)6] + 2K+ 89 K2Na[Co(NO2)6]5 + 2Na+
.
3. Cl.
. 1. ,
, , = . .:
NaCl + AgNO3 89 AgCl5 + NaNO3
2AgNO3 + K2CrO4 89 Ag2CrO45 + 2KNO3
2. , ,
, = . .:
AgNO3 + NH4SCN 89 AgSCN5 + NH4NO3
3NH4SCN + Fe(NH4)(SO4)2 89 Fe(SCN)3 + 2(NH4)2SO4
3. , , , = . .:
2NaCl + Hg(NO3)2 89 HgCl2 + 2NaNO3
2O 0C
NH8NH8C6H5
N0N8C6H5
+ Hg(NO3)2 89
43
C6H5
C6H5
NH8N
N8HN
Hg
O0 C
C6H5
C0 O + 2HNO3
C6H5
:
Na2[Fe(CN)5NO] + Hg(NO3)289Hg[Fe(CN)5NO]5 + 2NaNO3
. .
.
.
(
); .
(Natrii bromidum*) NaBr
(Kalii bromidum*) KBr
. , . . ;
10 .
.
Fe + Br2 89 FeBr2
3FeBr2 + Br2 89 Fe3Br8 (FeBr22FeBr3)
- Na2CO3
K2CO3:
Fe3Br8 + 4Na2CO3 + 4H2O
8NaBr + 4CO26 +
+ Fe(OH)25 + 2Fe(OH)35
. 1. K+ Na+.
2. Br:
) :
Ag+ + Br 89 AgBr5

;
) :
44
Cl
SO2N
Na
+ 2HCl 89 Cl2 + NaCl +
SO2NH2
2Br + Cl2 89 Br2 + 2Cl

- ;
) H2SO4:
Cu2+ + 2Br 89 CuBr25
, , .
. 1. , , H2SO4 BaSO4,
CaSO4 Br2:
BrO3 + 5Br + 6H+ 89 3Br2 + 3H2O
2. (III) :
2Fe3+ + 2I 89 2Fe2+ + I2
. .
. , ,
.
. .
(Natrii iodidum) NaI
(Kalii iodidum) KI
. , (NaI)
- (KI) .
. , .
. , .
. 1. Na+ K+.
2. I:
) :
Ag+ + I 89 AgI5
, ;
) , ,
:
2NaI + 2NaNO2 + 2H2SO4 89I2 + 2NO6 + 2Na2SO4 + 2H2O
45
) (III) :
2I + 2Fe3+ 89 I2 + 2Fe2+
,
:
2CN + Fe2+ 89Fe(CN)2
Fe(CN)2 + 4NaCN 89Na4[Fe(CN)6]
3Na4[Fe(CN)6] + 4FeCl3 89Fe4[Fe(CN)6]35 + 12NaCl
. 1. ,
, , = . .:
NaI + AgNO3 89 AgI5 + NaNO3

.
2. , , = 2. .
4KI + Hg(NO3)2 89 K2[HgI4] + 2KNO3
(II)
(II) , :
K2[HgI4] + Hg(NO3)2 89 2HgI25 + 2KNO3
.
.
. ( )
.

( )
,
, , 5 %-, 10 %-, , .
(Iodum)
I2
. -
.
,
46
. , , 10 95 %- ,
. .
. (0,5 %).

:
1.
.
2. -
:
2NaI + 2NaNO2 + 2H2SO4 89I2 + NO6 + 2Na2SO4 + 2H2O
3. .
4.
:
3I2 + 6NaOH 895NaI + NaIO3 + 3H2O
I2 + Na2SO3 + H2O 89 2HI + Na2SO4
5. :
2I + Cl289 I2 + 2Cl
6. .
.

.

(. ).
. , , = 1/2. .:
I2 + 2Na2S2O389 2NaI + Na2S4O6
. ,
.
. .
5 %-
(Solutio Iodi spirituosa 5 %)
: 50 ;
20 ;
(95 %-) 1 .
. - .
47
.
- .
. , = 1/2. .:
I2 + 2Na2S2O3 89 2NaI + Na2S4O6
, E = . .:
2NaI + KI + 3AgNO3 89 3AgI5 + KNO3 + 2NaNO3
, %, :
X KI =
(VAgNO
K VNa
2S2O3
K T 100
2 %.
. ,
.
. .
10 %-
(Solutio Iodi spirituosa 10 %)
: 100 ;
95 %- 1.
.
5 %-.
.
, :
C2H5OH + I2 89 2HI + CH3C
O
H
.
.
,
, :
I2 + KI 89 K[I3]
K[I3] + 2Na2S2O3 89 KI + 2NaI + Na2S4O6
9,510,5 %.
. 1 .
. .
48
(Iodinolum)
:
1 ;
3 ;
9 ;
1 .
5 %- .

VII ( ) .
(Kalii permangnas)
KMnO4
. --
. . ,
( ), .
.
2MnO2 + 4KOH + O2 89 2K2MnO4 + 2H2O
2K2MnO4 + Cl2 89 2KMnO4 + 2KCl
. 1.
:
2KMnO4 + 5H2O2 + 3H2SO4 89 2MnSO4 + K2SO4 + 5O26 + 8H2O
2. K+ ( ):
2KMnO4 + 3C2H5OH 89 2KOH + 2MnO25 + 3CH3C
O
H
+ 2H2O
. , , , = 1/5. .:
2KMnO4 + 10KI + 8H2SO4 89 2MnSO4 + 6K2SO4 + 5I2 + 8H2O
I2 + 2Na2S2O3 89 2NaI + Na2S4O6
. .
. .
49

, -
, . ,
.

(Solutio Hydrogenii peroxydi diluta)
H2O2
. , .
, , ,
, .
0,05 % .
.
. :
H2SO4 + HOH 89 H3O+ + HSO4
2H3O+ + 2e 89 2H3O
2HSO4 2e 89 2HSO4
2H3O 89 2H2O + H26
2HSO4 89 H2S2O8
(50 , 38 . .)
7075 :
HO
O
S
HOH
HOH
O
O
89
S
HO
HO
HO
HO
+ 2
O
S
HO
2,73,3 % .
. :
50
K2Cr2O7 + H2SO4 89 H2Cr2O7 + K2SO4
HO8Cr8O8Cr8OH + H2O2 89
O
89 HO8Cr8O8O8Cr8OH + H2O
HO8Cr8O8Cr8OH + 5H2O2 89
O
89 HO8Cr8O8O8Cr8 OH + 5H2O
:
Cr6+ 89 Cr3+
. ,
, = 1/2. .:
2KMnO4 + 5H2O2 + 3H2SO4892MnSO4 + K2SO4 + 8H2O + 5O26
() (
), , = . .:
COONa
COOH
+ HCl 89
+ NaCl

.
. , .
. ,
. .
51
(Hydroperitum)
O=C
NH2
NH2
H2O2
0,08 %- .
. .
, .
. 1.
:
O0 C
NH2
NH2
HN0 C0 O + O0C
NH 2
HN0 C 0 O + NH36
NH 2
H2N8 C 8NH8 C 8NH2

O
O0C8NH8C0O 12 O0 C8 NH8 C8 OH
NH2
NH2
NH2
O
2+
Cu ; KOH
NH
89 O0C8NH8C8OK
H2N
N
Cu/2
2. .
(1 15
3 %- ).
. , , = 1/2. .
2KI + H2O2 + H2SO4 89 I2 + K2SO4 + 2H2O
I2 + 2Na2S2O3 89 2NaI + Na2S4O6
35 %.
. , +20 .
. . .
52
(Magnesii peroxydum)
MgO2 + MgO
. . , .
. MgCl2 + 2KOH 89 2KCl + MgO + H2O
MgO + H2O2
89 MgO2 + H2O
. 1. Mg2+ :
MgCl2 + Na2HPO4 + NH3 89 MgNH4PO45 + 2NaCl
2. .
. ,
, = 1/2. .:
MgO2 + H2SO4 89 MgSO4 + H2O2
5H2O2 + 2KMnO4 +3H2SO4892MnSO4 + K2SO4 + 8H2O + 5O26
25,9 %
.
. , .
.
.
,
, .
,
,
.
(Natrii thiosulfas)
Na2S2O35H2O
. , . ,
. , .
. :
2CaS2 + 3O2 89 2CaS2O3
CaS2O3 + Na2SO4 89 Na2S2O3 + CaSO45
53
. 1. :
Na2S2O3 + 2HCl 89 2NaCl + SO26 + S5 + H2O
2.
, , , :
Na2S2O3 + 2AgNO3 89 Ag2S2O35 + 2NaNO3
5Ag2S2O3 89 Ag2SO35 + S5
5Ag2SO3 + 5S + H2O 89 Ag2S5 + H2SO4
Na+.
3.
:
Na2S + Na2[Fe(CN)5NO] 89 Na4[Fe(CN)5NOS]
.
. , , , = . .:
I2 + 2Na2S2O3 89 2NaI + Na2S4O6
. .
. , .
.
(Natrii sulfas)
Na2SO410H2O
. , ,
, - . 3 , .
. .
. ( ).
. .
. .
(Sulfur praeipitatum)
. - .
, , .
.
54
.
(Sulfur depuratum) . - .
. 1. SO2.
2. .
. - ;
, = 1/2. . .
:
12S + 6KOH 89 2K2S5 + K2S2O3 + 3H2O
, :
K2S5 + 8KOH + 16H2O2 89 5K2SO4 + 20H2O
K2S2O3 + 2KOH + 4H2O2 89 2K2SO4 + 5H2O
: S + 2KOH + 3H2O2 89 K2SO4 + 4H2O
.

99 %.
. .
.
, , .
.

III, IV V
III, IV V ,
, , , ,
, , , , ,
.
,
: ,
10 %-.
55
(Nitrogenium oxydulatum)
N2O
. , ,
, . , .
1520 C
.
.
NH4NO3
2H2O + N2O6 + Q
1523 (150
225).
. 1.
.
2.
( ).
.
:
, , , , , , , .
. 10 , .
.
( 80, 20 %).
(Natrii nitris)
NaNO2
.
, . .
, .
:
NaNO3 + Pb 89 PbO + NaNO2
. 1.
.
2. -:
) :
. H SO"
NO2 + 2
N
H
56
89
HSO4
) :
2NaNO2 + H2SO4 89 NO26 + NO6 + Na2SO4 + H2O
-
) - :
CH3
N CH3
NaNO 2
HCl
N
O
C6H5
CH3
N CH3
C6H5
. ,
, , = 1/2M. .:
5NaNO2 + 2KMnO4 + 3H2SO4 89
89 2MnSO4 + K2SO4 + 5NaNO3 + 3H2O
2KMnO4 + 10KI + 8H2SO4 89
89 5I2 + 6K2SO4 + 2MnSO4 + 8H2O
I2 + 2Na2S2O3 89 2NaI + Na2S4O6
.
.
.
. ,
.
(Solutio Ammonii concentrata)
NH4OH
10 %- (Solutio Ammonii caustici)
. , . 95 %-
.
.
:
N2 + 3H2 89 2NH3
.
57
. , ,
:
NH3 + HCl 89 NH4Cl
. - ,
, = . .:
2NH4OH + H2SO4 89 (NH4)2SO4 + 2H2O
.
. .
.
.
,
As2O3, , KAsO2 ( ), .
(Acidum arsenicosum anhydricum)
As2O3
. - , ,
. (6880 ), HCl, KOH, K2CO3, :
As2O3 + 6HCl 89 2AsCl3 + 3H2O
As2O3 + 2KOH 89 2KAsO2 + H2O
As2O3 + K2CO3 89 2KAsO2 + CO26
. :
2As2S3 + 9O2 892As2O3 + 6SO26
2FeAsS + 5O2 89As2O3 + 2SO26 + Fe2O3
. 1.
,
NH4OH, (NH4)2CO3:
As2O3 + 6HCl 89 2AsCl3 + 3H2O
2AsCl3 + 3Na2S 89 As2S35 + 6NaCl
58
2.
, HNO3
NH4OH:
Na3AsO3 + 3AgNO3 89 Ag3AsO35 + 3NaNO3
. , , , = 1/4. .
:
3As2(SO4)3 + 2KBrO3 + 18H2O 89 6H3AsO4 + 2KBr + 9H2SO4
5KBr + KBrO3 + 3H2SO4 89 3Br2 + 3K2SO4 + 3H2O
. .
. ,
, .
(Bismuthi subnitras)
. :
NO3
Bi OH ,
OH
O
Bi
NO3
Bi
OH
O
OH
O 0Bi8O8Bi
NO3
. ;
, ; HCl, HNO3.

(pH < 7).
OH
O 0Bi8O8Bi
NO3
+ H2O 89 HNO3 + 2Bi
O
OH
Bi2O3 + 3C 89 2Bi + 3CO6

Bi + 4HNO3 89 Bi(NO3)3 + NO6 + 2H2O
NO3
Bi NO3 + HOH
NO3
HNO3
Bi
NO 3
NO 3
OH
O
HNO3
. 1. Bi3+:
) :
2Bi3+ + 3S2 89 Bi2S35
59
Bi
NO3
) ,
:
Bi(NO3)3 + 3KI 89 BiI35 + 3KNO3
5BiI3+KI 89K[BiI4]
2. - :
OH
2O 0Bi8O8Bi
NO3
2Bi2O35 + 2NO26 + 1/2O26 + H2O
. ,
, , = 1/2. .
Bi2O3:
H3Ind + Bi3+ 89 BiInd + 3H+
Bi3+ +
H2C&N
H2C&N
CH2COONa
CH2COOH
CH2COOH
89
CH2COONa
CH2COO
H2C&N
CH2COO
89
H2C&N
H2C&N
BiInd +
H2C&N
Bi Na+ + Na+ + 2H+
CH2COO
CH2COO
CH2COONa
CH2COOH
89
CH2COOH
CH2COONa
H2C&N
89
H2C&N
CH2COO
CH2COO
CH2COO
Bi Na+ + H3Ind + Na+
CH2COO
,
79 82 %.
60
. , .
. , .
,
.
(Carbo activatus)
.
.
800 . .
, ,
300400 C.
,
. .
(d = 101103 )
(d = 9,2107 ).
. 1
10002.
.
, .
, , , , . , .
.
. , .
. , ,
, .
(Natrii hydrocarbonas)
NaHCO3
. , - , , . ,
95 %- . .
. ():
61
NH3 + CO2 + H2O 89 NH4HCO3

NH4HCO3 + NaCl 89 NH4Cl + NaHCO35
. 1. Na+.
2. HCO3 :
)
:
NaHCO3 + HCl 89 CO26 + NaCl + H2O
) MgSO4
, , .
4MgSO4 + 8NaHCO3
893MgCO3Mg(OH)23H2O5 + 4Na2SO4 + 5CO26

. , , , = . .:
NaHCO3 + HCl 89 NaCl + CO26 + H2O
. .
.
.
,
. 90 , .
,
.
,
.
(Acidum boricum)
H3BO3
. , , ,
. ( 100 C)
HBO2, , , , B2O3.
. 25 ,
4 .
62
.
:
1. Na2B4O710H2O + 2HCl 89 4H3BO3 + 2NaCl + 5H2O
2. B2O32MgOH2O + 2H2SO4
110 C
2MgSO4 + 2H3BO3
. 1. :
OC2H5
H3BO3 + 3C2H5OH 89 3H2O + B OC2H5
OC2H5
2. :
HO
HO
HO 8C 8CH 0CH
B8OH +
OH
OCH3
OCH3 889
CH
O 0 C 8 CH 0CH
OH
O 8 C8 CH 0 CH
89
HO
HO
OH
OCH3
OCH3
CH
O 0 C8 CH 0 CH
OH

-.
. , ,
, , = . .:
H2C 8OH
HC 8OH +
H2C 8OH
HO
HO
HO 8 CH2
B8OH + HO 8 CH 89
HO 8 CH2
63
H2C8 OH
89
HC 8 O
H2C8 O
HO 8 CH2
O 8 CH H + NaOH 89
O 8 CH2
H2C8 OH
89
HO 8 CH2
HC 8 O
O 8 CH
H2C8 O
Na + H2O
O 8 CH2

NaBO2,
. , .
. .
. , (24 %) , ,
, (510 %) .
() (Natrii tetraboras)
Borax*
Na2B4O71OH2O
. , , , . ,
, , . -
. .
CH2 OH
CH2 OH
8 CHOH + Na2B4O7 89 2 HC 8 O
CH2 OH
H2C8 O
CH2 OH
+ 2
HC 8 O
64
O 8 CH
+
H +
O 8 CH2
HOCH2
B
H2C8 O
HOCH2
O 8 CH Na+ + 7H2O
O 8 CH2
. :
CaB4O7 + Na2CO3 89 Na2B4O7 + CaCO35
.
. 1. . .
2. Na+.
. 1. , , , = 1/2. .:
Na2B4O7 + 2HCl + 5H2O 89 4H3BO3 + 2NaCl
2. (. ),
= 1/2. .
. .
. .
( ).

( ) : 8,8 %,
.
.
(Aluminii hydroxydum)
Algeldratum*
Al(OH)3
. .
, .
.
Al2(SO4)3 + 6NH4OH 89 2Al(OH)3 + 3(NH4)2SO4
60 C
2KAl(SO4)2 + 6NH4OH 89 2Al(OH)3 + K2SO4 + 3(NH4)2SO4
.
( ):
2Al(OH)3
2Co(NO3)2
Al2O3 + CoO
t
t
t
65
Al2O3 + 3H2O
2CoO + 4NO26 + O26
Co(AlO2)2
. Al2O3,
.
. .
. ,
; .

(Al(OH)3MgO).

II
II ( ) ( ) .
, , , .
,
, . 2 %. , : MgCO3CaCO3, MgCO3,
3MgO 4SiO2H2O.
; , , , , ,
.
(Magnesii oxydum*)
MgO
. , , ; , . , ,
.
.
9001000 :
3MgCO3Mg(OH)23H2O 89 4MgO + 3CO26 + 4H2O
. :
MgO + 2HCl 89 MgCl2 + H2O
66
1. Mg2+:
MgCl2 + Na2HPO4 + NH4OH
NH4Cl
MgNH4PO45+2NaCl + H2O
.
2.
.
8-,
- :
NH4OH
+ MgCl2 889
NH Cl
4
+ 2HCl
O
Mg
. 1. ,

, , = . .:
OH
H2O
NaO3S
OH2
H2C8N
N0N
H2C8N
CH2COONa
CH2COOH
CH2COOH
89
CH2COONa
O2N
H2C8N
89
H2C8N
CH2COO
CH2COO
CH2COO
Mg 2Na +
CH2COO
OH
+ NaO3S
OH
N0N
O2N
2. - .
1 ,
67
1
, = 1/2. .:
MgO + 2HCl 89 MgCl2 + H2O
.
HCl + NaOH 89 NaCl + H2O
. ,
, ,
:
MgO + CO2 89 MgCO3
MgO + H2O 89 Mg(OH)2
.
( ,
).
, ,
. .

.
(Magnesii sulfas*)
MgSO47H2O
. , , - . 1 ,
0,3 , .
. :
MgCO3 + H2SO4 89 MgSO4 + CO26 + H2O
.
:
MgOH
MgOH
. 1. Mg2+.
2. SO42:
MgSO4 + BaCl2 89 BaSO45 + MgCl2
. .
(68
),
; . - (-).
2Mn2+ + 5S2O82 + 8H2O
AgNO 3

2MnO4 + 10SO42 + 16H+
0,01
,
.
. ,
,
, = . .
. ( ).
. , , .
.

.
(Magnesii subcarbonas*)
3MgCO3Mg(OH)23H2O
. , .
.
.
.
4MgSO4 + 4Na2CO3 + 4H2O 89
89 3MgCO3Mg(OH)23H2O5 + 4Na2SO4 + CO26
. 1. .
2. (
):
3MgCO3Mg(OH)23H2O + 8HCl 89
89 4MgCl2 + 3CO26 + 8H2O
. ,
, .
, , 4044 %, = . . MgO.
. .
. .
69
;
, , ; .

(, , ), ( CaSO42H2O, CaSO4), ( CaF2), (,
).
(Calcii chloridum*)
CaCl26H2O
. , -
, , ,
,
, 95 %- ;
34 C .
.
:
CaCO3+2HCl89CaCl2+H2O+CO26
, MgCl2
FeCl2. (FeCl2
FeCl3), :
2FeCl3+3Ca(OH)2 892Fe(OH)35+3CaCl2
MgCl2+Ca(OH)2 89Mg(OH)25+CaCl2
,
, . :
Ca(OH)2+2HCl 89CaCl2+2H2O
. 1. Ca2+:
) - ;
)
:
CaCl2+(NH4)2C2O4 89CaC2O45+2NH4Cl
.
70
2. Cl.
. ,
,
-, = . .:
H2O
O
OH2
Ca
OH
H2C8N
N0N
NaO3S
H2C8N
SO3Na
CH2COONa
CH2COOH
89
CH2COOH
CH2COONa
H2C8N
89
H2C8N
CH2COO
CH2COO
CH2COO
Ca 2Na+ +
CH2COO
OH
OH OH
N0N
NaO3S
SO3Na
.
.
,
50 %-
.
. ,
, , , , .
,
,
, , ,
, ,
.
: BaSO4 , BaCO3 .
71
(Barii sulfas)
BaSO4
. ,
, .
.
:
BaCl2 + Na2SO4 89 BaSO45 + 2NaCl
,
. -
, (,
).
. :
BaSO4 + Na2CO3 89 BaCO35 + Na2SO4
.

(-):
Na2SO4 + BaCl2 89 BaSO45 + 2NaCl

( ):
BaCO3 + 2HCl 89 BaCl2 + H2O + CO26
BaCl2 + H2SO4 89 BaSO45 + 2HCl
.
(50100 ),
.
,
, , .
;
:
BaCO3 + 2HCl 89 BaCl2 + CO26 + H2O
BaS + 2HCl 89 BaCl2 + H2S6

,
, (II)

.

72
, .

.
.
. .
.
( ),
,
.
.
.
,
:
ZnS; ZnCO3;
Zn4(Si2O7)(OH)2H2O.
.
,
.
, ,
, .
, ,
.
(Zinci oxydum*)
ZnO
. ,
. ,
, .
.
. 1. :
ZnCO3 89 ZnO + CO26
2. 250 C , :
5ZnSO4 + 5Na2CO3 + 3H2O 89
89 2ZnCO33Zn(OH)25 + 5Na2SO4 + 3CO26
2ZnCO33Zn(OH)2
73
5ZnO + 2CO26 + 3H2O
. 1. ,
.
2. Zn2+.

:
ZnO + 2HCl 89 ZnCl2 + H2O
) :
ZnCl2 + Na2S 89 ZnS5 + 2NaCl
) :
3ZnCl2 + 2K4[Fe(CN)6] 89 K2Zn3[Fe(CN)6]25 + 6KCl
)
(II)
( ):
ZnO + Co(NO3)2 89 CoZnO2 + 2NO26 + 1/2O26
. .
.
, ,

:
PbO + 2CH3COOH 89 (CH3COO)2Pb + H2O
(CH3COO)2Pb + K2CrO4 89 PbCrO45 + 2CH3COOK
. ,
,
, = . .
. ,

.
. , ,
,
.
,
.
0,020,05 23 ( )
2 %- .
(Zinci sulfas*)
ZnSO47H2O
.
. .
74
. ,
, 10 .
.
:
Zn + H2SO4 89 ZnSO4 + H26
ZnO + H2SO4 89 ZnSO4 + H2O
. 1. - (. ).
2. .
. ,
,
, , = . .
. .
. ( 0,1; 0,25; 0,5 %),
, (0,10,5%).

(0,10,3 ). 1.
,
.
3000
.
.
, .
HgS
- .
() (Hydrargyri dichloridum*)
HgCl2
. . ( ). H[HOHgCl2].
:
HgCl2 + 2NaCl 89 Na2[HgCl4]
H[HOHgCl2] + 2NaCl 89 Na2[HgCl4] + H2O
,
, .
75
. 1.

. , (II) .
, :
Hg + 2H2SO4 89 HgSO4 + 2H2O + SO26
HgSO4 + 2NaCl
HgCl26 + Na2SO4
2. 335340 C :
Hg + Cl2 89 HgCl2

Hg2Cl2.
,
, .
. 1. Cl.
2. (II)
. ,
:
5HgI2 + 2KI 89 K2 [HgI4]
. , , , = 1/2. .
:
HgCl2 + HC
O
H
+ 3KOH 89 Hg5 + HCOOK + 2KCl + 2H2O
0,1
:
5Hg + I2 89 HgI25
5HgI2 + 2KI 89 K2 [HgI4]
:
I2 + 2Na2S2O3 89 2NaI + Na2S4O6
. .
. , .
.
:
.
76
(1:10002:1000)
, , ,
. .
.
(Hydrargyri oxydum flavum)
HgO
. -, , , .
. , ,
, .
.
:
HgCl2 + 2NaOH 89 HgO5 + 2NaCl + H2O
,
,
, , :
Hg
Cl
OH

. :
, . .
.
HgO + 2HCl 89HgCl2 + H2O

(II)
, :
HgCl2 + 2KI 89HgI25 + 2KCl
5HgI2 + 2KI 89K2[HgI4]
. (I) :
Hg22+ + 2Cl 89 Hg2Cl25
77
. , . ,
. , ,
, = 1/2. .:
HgO + 4KI + H2O 89 K2HgI4 + 2KOH
2KOH + 2HCl 89 2KCl + 2H2O
. .
, (I) ,
.
.
.
(Hydrargyri oxycyanidum)
HgOHg(CN)2
. . . .
. , (II) , (III) .

HgI2. , :
H2OHg(CN)2 + 2HCl 89 Hg(CN)2 + HgCl2 + H2O
5HgI2 + 2KI 89 K2[HgI4]
Hg(CN)2 + 4KI 89 K2[HgI4] + 2KCN
2KCN + FeSO4 89 Fe(CN)2 + K2SO4
Fe(CN)2 + 4KCN 89 K4[Fe(CN)6]
K4[Fe(CN)6] + 4FeCl3 89 Fe4[Fe(CN)6]2 + 12KCl
. (II)
, , ,
= 1/2. .:
HgOHg(CN)2 + 2HCl
NaCl
HgCl2 + Hg(CN)2 + H2O
45,7 % HgO.
78
, = 1/2. .:
Hg(CN)2 + 4KI 89 K2HgI4 + 2KCN
2KCN + 2HCl 89 2HCN + 2KCl
53,3 % Hg(CN)2.
. .
. .

I VIII
I : ( ) ( ). : ,
, .
, . 2+.

,
Cu2+ Cu+, Ag+ .

I
.
: (II) , , , .
(Cupri sulfas*)
CuSO45H2O
. , , . . , ,
95 %- . :
CuSO4 + 2HOH 12 Cu(OH)2 + H2SO4
79
. :
3Cu + 3H2SO4 + 2HNO3 89 3CuSO4 + 4H2O + 2NO6
( H2SO4, HNO3, NO),
CuSO45H2O.
. 1. Cu2+:
) (1 : 20) :
CuSO4 + 5Fe 89 FeSO4 + Cu5
)
:
2CuSO4 + 2NH4OH 89 (NH4)2SO4 + Cu2(OH)2SO45

- :
5Cu2(OH)2SO4 + 6NH4OH + (NH4)2SO4 89
89 2[Cu(NH3)4]SO4 + 8H2O
Cu2+:
)
,
:
CuSO4 + Na2S 89 CuS5 + Na2SO4
53CuS + 8HNO3 89 3Cu(NO3)2 + 3S5 + 2NO6 + 4H2O
) - , :
2CuSO4 + K4[Fe(CN)6] 89 Cu2[Fe(CN)6]5 + 2K2SO4
) (II)
, - (,
.) .
2. SO42.
. , , ; = ..:
2CuSO4 + 4KI 89 2CuI2 + 2K2SO4
2CuI2 89 Cu2I25 + I2
80
I2 + 2Na2S2O3 89 2NaI + Na2S4O6

. .
. , , , .
(Argenti nitras)
AgNO3
. . , .
. -
:
AgCu + 4HNO3
AgNO3 + Cu(NO3)2 + NO6 + 2H2O
. 1. Ag+:
)
, :
AgNO3 + HCl 89AgCl5 + HNO3
5AgCl + 2NH4OH 89[Ag(NH3)2]Cl + 2H2O
) :
AgNO3 + 2NH4OH 89 [Ag(NH3)2]NO3 + 2H2O
2[Ag(NH3)2]NO3+R8C
O
H
+ H2O89
892Ag5 + R8C
O
ONH4
+ NH36 + 2NH4NO3
2. NO3 (
NO2, . ).
. , , , = . .:
3NH4SCN + FeNH4(SO4)2 89 Fe(SCN)3 + 2(NH4)2SO4

.
. ,
.
. , .
81
( ) .

,
.
AgNO3
:
AgNO3 + NaOH 89 AgOH5 + NaNO3
25AgOH 89 Ag2O5 + H2O
Ag2O
.
, .
70 % .
8 % 92 %
.
(Collargolum)
. - -
. .
. 1. , .
2.
.
AgCl.
3. (. ).
4. : (1 : 50)
- .
.
.
, (. ). 70 %.
. ,
.
. , , .
,
82
, .
(Protargolum)
. - , - . ,
95 %- , . .
, , , . .
7,88,3 %.

VIII d-, , , . ,
. , , ,
.
Fe2+, .
(Ferri sulfas)
FeSO47H2O
. - . .
.
. 25
30 %- 80 C:
Fe + H2SO4 89 FeSO4 + H26
30 C,
64 C .
. 1. -.
2. Fe2+:
) :
FeSO4 + K3[Fe(CN)6] 89 FeK[Fe(CN)6]5 + K2SO4
)
.
83
. , ,
= . .:
10FeSO4 + 2KMnO4 + 8H2SO4 89
89 5Fe2(SO4)3 + K2SO4 + 2MnSO4 + 8H2O
. ,
.
. .

.
, - , ,
, . .

.

- .
, , .

.
-
-,
.
, .
84
:
1) ;
2) ;
3) .
, , 99,5 %.
.
:

;
;
,
,
.

() .
, ,
, - ,
. , - -,
.
, -32, 2-, -131, .
, -32,
(Solutio Natrii phosphatis phosphoro-32 notati pro injectionibus)
Na2H(32P)O4
. . 2
10/. 32P 98 %.
. 1. .
2. -
-
32.
85
3. 14,2 .
( ).

-
32.
. ( ).
410 /.
. .
2 .
. , , , .
-, -131,
(Solutio Natrii o-iodhippuratis Iodo-131 notati pro injectionibus)
CONHCH2COONa
131
. .
0,1/.
- 98 %.
. -.
8 .
( ).
- -.
. -.
.
410 C. 20 .
. .

:
; ; ;
, - ; .
; , .
; ;
- ; .
,
.
;
; ; ; .

. .
, .
, . , .
87
,
( ), ,
.
,
, () .
(Chloroformium)
CHCl3
. , , , ,
. . , , ,
, . :
2CHCl3 + O2 89 2CCl3(OH) 89 2COCl2 + 2HCl
2COCl2 + O2 89 2CO26 + 2Cl26

(0,61 %):
O=C
Cl
Cl
+ 2C2H5OH 89 O=C
Cl2 + C2H5OH 89 CH3C
OC2H 5
+ 2HCl
OC2H 5
+ 2HCl
HCl + C2H5OH 89 C2H5Cl + H2O

. :
2NaCl + 2H2O
2NaOH + Cl2 + H2
2NaOH + Cl2 89 NaClO + NaCl + H2O

C2H5OH + NaClO 89 CH3C
CH3C
O
H
O
H
+ 3NaClO 89 CCl3C
88
O
H
+ NaCl + H2O
+ 3NaOH
CCl3C
O
H
+ NaOH 89 CHCl3 + HCOONa
. .
. .
:
Cl2 + 2KI 89 I2 + 2KCl
.
:
RC
O
H
+ K2HgI4 + 3KOH 89 RC
O
OK
+ Hg5 + 4KI + 2H2O

, ,
, = 1/4. .:
3C2H5OH + 2K2Cr2O7 . + 16HNO3 89
89 4Cr(NO3)3 + 3CH3COOH + 4KNO3 + 11H2O
K2Cr2O7 + 6KI + 14HNO3 89
89 8KNO3 + 2Cr(NO3)3 + 3I2 + 7H2O
I2 + 2Na2S2O3 89 2NaI + Na2S4O6
. ,
.
. , . , , .
.
(Iodoformium)
CHI3
. -
. ,
. ,
89
. .
.
:
C2H5OH + 4I2 + 3Na2CO3 89
89 CHI35 + 5NaI + HCOONa + 2H2O + 3CO26
. :
2CHI3 + 2O2 89 3I26 + CO6 + CO26 + H2O
. .
. ,
= 1/3. .
CHI3 + 3AgNO3 + H2O
3AgI5 + 3HNO3 + CO6

Fe3+ + 3SCN 89 Fe(SCN)3
.
. , ,
.
. . , , , .
(Aethylii chloridum)
C2H5Cl
. , . ,
. 12,5 .
. 1. :
C2H6 + Cl2 89 C2H5Cl + HCl
2. :
CH2 0 CH2 + HCl 89 CH3CH2Cl
.
:
C2H5Cl + KOH 89 C2H5OH + KCl
C2H5OH + 4I2 + 6KOH 89 CHI35 + 5KI + HCOOK + 5H2O
90
.

(. ).
. ,
, .
. .
(Phthorotanum)
Halothane*
CF3 CHClBr
1,1,1--2--2-
. , , ,
, , ,
.
0,01 % , .
, , ,
, , .
. 1,1,1--2-:
CF3 8CH2Cl + Br2 89 CF38CHClBr + HBr
. (, , ).
(1,8651,87), ,
,
.
. - -:
Zr/4
OH
+ 6F
SO3Na
OH
OH
+ [ZrF6]2
89
O
91
SO3Na
- .
TiO2,
.
. ,
, , .
6
.
. . . .

,
. -, . .
. ,
, .

. ( 16 ) .
, , .
(Spiritus aethylicus)
CH3 8CH2OH
. , , , . 78 C.
, , .
, , , .
. :
; 60
H2O;
2(C6H10O5)n + nH2O 88889 nC12H22O11 88889
; 3033
89 2nC6H12O6 888889
4nC2H5OH + 4nCO26
92
, , , .
.
.
( , ) :
1. ( ):
CH3C
O
OH
+ HOCH2CH3
. H2SO 4
H 2O
CH3C
O
OC2H5
2. :
C2H5OH + 4I2 + 6KOH 89 CHI35 + 5KI + HCOOK + 5H2O
.
3.

, . ,
,
( ).
.

.
:
5CH3OH + 2KMnO4 + 3H3PO4 89
89 5HC
O
H
+ 2MnHPO4 + K2HPO4 + 8H2O
.
:
SO3Na
2
HO
+ HC
HO
. H2SO 4
SO3Na
93
HO3S
SO3H
89
HO
CH2
OH
HO
[O]
OH
SO3H
89
HO3S
SO3H
HO
HO3S
CH
HO
OH
SO3H
HO3S
( ):
O
CH3C
+ 2[Ag(NH3)2]NO3 + H2O 89

89 2Ag5 + 2NH4NO3 + NH36 + CH3C
O
ONH4
O + H 2N
H
H2O
. .
(.
).
.
. , .
.
, , , .
95, 90, 70 40 %- .
94
(Glycerinum)
CH28 CH8 CH2

OH OH OH
1,2,3-
. , , .
- .
. :
O
H2COCR
O
HCOCR
H2C8OH
OH
HC8OH + 3RCOO
O
H2COCR
H2C8OH
. (
):
H2C8OH
HC8OH
H
+ 2H2O
CH
KHSO4; t
H2C8OH
CH2
. () . .
1. :
CH2OH
CH2OCOCH3
CHOH + 3(CH3CO)2O 89 CHOCOCH3 + 3CH3COOH

CH2OH
CH2OCOCH3
, ,

:
95
CH2OCOCH3
CH2OH
CHOCOCH3 + 3NaOH 89 CHOH + 3CH3COONa

CH2OCOCH3
CH2OH
, , ,
= 1/3. .
2. , , , = 1/14. .:
3C3H5(OH)3 + 7K2Cr2O7 + 28H2SO4 89
89 9CO26 + 7K2SO4 + 7Cr2(SO4)3 + 40H2O
:
Cr2O72 + 6Fe2+ + 14H+ 89 2Cr3+ + 6Fe3+ + 7H2O
. .
. . .
, .
.
, , , .
, , .
40 %- (Solutio Formaldehydi)
(Formalinum)
H8 C
O
H
. ,
. .
96
( ).
( 1 %).
. 1. :
500600 C
Kt
2CH3OH + O2
2H8 C
+ 2H2O
2. :
O2
2CH4 + O2 89 2CH3OH
2H8 C
O
H
+ 2H2O
. 1. :
HC
O
H
+ 2[Ag(NH3)2]NO3 + H2O 89
89 HCOONH4 + 2Ag5 + NH36 + 2NH4NO3
2. :
COOH
2
+ HC
O
H
OH
. H2SO4
H2 O
HOOC
CH2
89
COOH
HO
OH
HOOC
89
[O]
H 2O
CH
HO
COOH
O
HO
HOOC
O
C
COOH
COOH
OH
97
. :
2HC
O
H
+ H2O 89 HC
O
OH
+ CH3OH
.
. 1. ,
, , = 1/2. .:
I2 + 2NaOH 89 NaI + NaOI + H2O
NaOI + HC
89 NaI + HCOOH
HCOOH + NaOH 89 HCOONa + H O

2

:
NaI + NaOI + H2SO4 89 I2 + Na2SO4 + H2O
.
2. , . , = . .:
HC
O
H
+ H2O2 + NaOH 89 HC
O
ONa
+ H2O
NaOH + HCl 89 NaCl + H2O

3. , , = . .:
HC
OH
+ Na2SO3 + H2O 89 HC 8H
+ NaOH
SO
Na
H
3
O

).
4. ( ).
. ,
, 9 ( ).
98
. ,
, . .
!
(Hexamethylentetraminum)
(Urotropinum)
Methenaminum*
N
. , , .
, . . .
, .
. :
HC
OH
+ NH3 89 HC 8NH2
H
H
O
H 2O
89
HN
CH20NH
NH
3HC
; NH3
3H 2O
N
H
:
6HC
O
H
+ 4NH3 89 (CH2)6N4 + 6H2O
. :
(CH2)6N4 + 2H2SO4 + 6H2O
6HC
O
H
+ 2(NH4)2SO4
:
(NH4)2SO4 + 2NaOH
99
2NH36 + Na2SO4 + 2H2O
. :
I8Hg
NH3 + KOH + 2K2[HgI4] 89
HC
O
H
+ K2[HgI4] + 3KOH
I8Hg
HC
NH2 I + 5KI + H2O
O
OK
+ Hg5 + 4KI + 2H2O
. 1. - , , = 1/4. .:
(CH2)6N4 + 2H2SO4 + 6H2O
.H2SO4
6HC
O
H
+ 2(NH4)2SO4
+ 2NaOH 89 Na2SO4 + 2H2O
.
2. ,
( ), = . .:
(CH2)6N4 + HCl 89 (CH2)6N4HCl
3. , , , = 1/4. .:
(CH2)6N4 + 2ICl 89 (CH2)6N42ICl5
.ICl
+ KI 89 I2 + KCl
I2 + 2Na2S2O3 89 2NaI + Na2S4O6

4. , = 2/3. .:
2(CH2)6N4 + 3AgNO3 . 89 2(CH2)6N43AgNO35
3NH4SCN + Fe(NH4)(SO4)2 89 Fe(SCN)3 + 2(NH4)2SO4
. .
. , . .
100
(Chloralum hydratum)
OH
CCl3C 8H
OH
1,1--2,2,2-
. . ; . ,
. :
O
2CCl3CH(OH)2 89 CHCl2C
+ CCl3COOH + HCl + H2O

.
.
:
2NaCl + 2H2O
C2H5OH
Cl2
2HCl
CH3C
Cl2 + 2NaOH + H26
OH
CH3C 8H
OC2H5
C 2H5OH
OH
89 CCl3C 8H
OC2H5
H 2SO4
CCl3C
H 2O
Cl2
HCl
OH
CCl3C 8H
OH
. 1. :
OH
CCl3C 8H + 2[Ag(NH ) ]NO 89
3 2
3
OH
O
89 2Ag5 + NH36 + CCl3C
+ 2NH4NO3
ONH4
2. :
CCl3CH(OH)2 + NaOH 89 CHCl35 + HCOONa + H2O
101
. ()

:
CCl3CH(OH)OC2H5 + NaOH 89 CHCl3 + HCOONa + C2H5OH
C2H5OH + 4I2 + 6NaOH 89 CHI35 + 5NaI + HCOONa + 5H2O
. 1. - , , = . .:
CCl3CH(OH)2 + NaOH 89 CHCl35 + HCOONa + H2O
.
.
2. , , ,
= 1/2. .:
2CCl3CH(OH)2 + 2I2 + 3Na2CO3 89
89 2CCl3COONa + 4NaI + 3H2O + 3CO26
I2 + 2Na2S2O3 89 2NaI + Na2S4O6
. , ,
.
. , ; , , . .

.
: ,
, .

, ,
. :
, , .
(Kalii acetas)
CH3COOK
.
, . , . ,
.
102
. :
2CH3COOH + K2CO3 89 2CH3COOK + H2O + CO26
. 1. +:
) ;
) :
K+ + H2C4H4O6 89 KHC4H4O65 + H+
) :
2K++Na3[Co(NO2)6] 89K2Na[Co(NO2)6]5 + 2Na+
2. -:
) ( ):
CH3COOK + C2H5OH + H2SO4 . 89
89 CH3C
O
OC2H5
+ H2O + KHSO4
) (III):
9CH3COOK + 3FeCl3 + 2H2O 89
89 2CH3COOH + [Fe3(OH)2(CH3COO)6]+CH3COO + 9KCl
- .
. 1. ,
, , = . .:
CH3COOK + CH3COOH 12 (CH3COOKH)+CH3COO
HClO4 + CH3COOH 89 (CH3COOH2)+ClO4
(CH3COOKH)+CH3COO + (CH3COOH2)+ClO4 89
89 KClO4 + 3CH3COOH
: CH3COOK + HClO4 89 CH3COOH + KClO4.
.
2. , , -00
( 1,33,2), = ..:
CH3COOK + HCl 89 CH3COOH + KCl
. , .
103
. ( ). , .
(Calcii lactas)
H3C8 CH8 C
OH
Ca2+5H2O
. .
. , , , .
. .
. 1. Ca2+:
) :
Ca2+
COO
COO
89
COO
COO
Ca
) - .
2. -:
5(CH3CHOHCOO)2Ca + 4KMnO4 + 11H2SO4 89 10CH3C
+ 5CaSO45 + 10CO26 + 2K2SO4 + 4 MnSO4 + 16H2O

, .
. ,
,
-, = . .:
H2 O
O
OH2
Ca
N0N
NaO3S
OH
+
SO3Na
104
CH
CH
N
CH COONa
CH COOH
89
CH COOH
CH COONa
N
89
CH2
CH2
N
CH2COONa
OH
CH2COO
OH OH
N0N
Ca +
NaO3S
CH2COO
SO3Na
CH2COONa
. .
. 2+. , .
(Calcii gluconas)
H H OH H
HOCH2CCCCC
OH OH H OH
O
Ca2+H2O
.
. 50 , 5 ,
.
.
:
CH2OH
(CHOH)4
O
C
H
CH2OH
CH2OH
Br 2; H 2O
2HBr
(CHOH)4
COOH
CaCO3
CO2
Ca2+
(CHOH)4
COO
. 1. Ca2+.
2. FeCl3 - (
-).
.
. (
), = . .
105
. .
.
(, ).
(Natrii citras pro injectionibus)
H2C 8 COONa
1H O
HO 8 C 8 COONa 5
2
2
H2C 8 COONa
.
, , . 1,5 ,
.
. :
H2C 8 COOH
2 HO 8C 8COOH + 3Na2CO3 89
H2C 8 COOH
H2C 8 COONa
89 2 HO 8 C 8 COONa + 3H2O + 3CO26
H2C 8 COONa
. 1. Na+.
2. -
, :
H2C8 COO
H2CCOONa
2 HOCCOONa + 3CaCl2
HO 8 C8 COO
Ca35 +
H2C8 COO
H2CCOONa
+ 6NaCl
106
3. ():
H2C 8 COONa
HO 8 C 8 COONa
H2C 8 COOH
H+
H2C 8 COONa
HO 8C 8COOH
H2C 8 COOH
KMnO 4; t
3CO2
2
CH3
89 C O
CBr3
5Br2
C 0O
5HBr
CHBr2
CH3
.
:
COO
COO
+ Ca2+ 89
COO
COO
Ca
. 1. :
H2 CCOONa
H2CCOOH
3[Kat]H+ + HOCCOONa 89 HOCCOOH + 3[Kat]Na+
H2 CCOONa
H2CCOOH
, , , , = 1/3. .:
H C`COOH
H C`COONa
HO`C`COOH + 3NaOH &' HO`C`COONa + 3H2O

H C`COOH
H C`COONa
2. , = 1/3. .:
H C`COOAg
H C`COONa
HO`C`COONa + 3AgNO3 &' HO`C`COOAg
+ 3NaNO3
H C`COOAg
H C`COONa

107
FeNH4(SO4)2+3NH4SCN 89 Fe(SCN)3 + 2(NH4)2SO4

. .
. ( ).
(Natrii hydrocitras pro injectionibus)
H2C 8 COONa
1
HO 8 C 8 COOH 1
H 2O
2
H2C 8 COONa
.

,
. - .
20 - :
COOH
CH 8NH 2
R
- ( H2NCH2COOH)

.
.
.
COOH NH2 , , :
R
HC8 COOH
+
NH3
Cl
HCl
CH8 COOH
NH2
108
NaOH
H2O
CH8 C
NH2
O
ONa
,
( ) , .

-, -, - .
.
:
- 2,5-
:
R8CH8 C
NH2
OH
NH2
t
H2O
C8CH8R
HO
NH
HN
R
O
-, ,
:
R8 CH8 CH2 8 COOH
t
NH3
RCH0CHCOOH
NH2
- :
R8 CH
NH2
CH2
CH2
R
t
H2O
HO 8 C
HN
O
:
- :
NH2
O
2
R8CH8COOH
NH2
Cu
2+
R8 CH8 C8 O8Cu8 O8 C8 CH8 R

H2N
- , ;
- .
109
. - :
O
OH2O + R8CH8COOH
NH2
O
89
+ NH36 + CO26
OH + R8C
H
H
O + H8N8H + HO
H
H
O
O
OH
NH 3
89
O
2H 2O
ONH4
N
. 1.
.

K2SO4, CuSO4 H2SO4:
HOOC8 CH28 CH28CH8 COOH
[O]; t
H2 SO4
NH2
89 CO26 + H2O + NH4HSO4
30 %- NaOH:
NH4HSO4 + 2NaOH
NH36 + 2H2O + Na2SO4
, , -, . - , HCl 110
( 2:1):
NH3 + H3BO3 89 NH4BO2 + H2O
2NH3 + 4H3BO3 89 (NH4)2B4O7 + 5H2O
NH4BO2 + HCl + H2O 89 NH4Cl + H3BO3
(NH4)2B4O7 + 5H2O + 2HCl 89 2NH4Cl + 4H3BO3

.

.
2. ( ). - ,
, .
N- , :
R8CH8 COO
NH3
+ HC
O
H
89 R8CH8 COOH + H2O
N=CH2
R8CH8 COOH + NaOH 89 R8CH8 COONa + H2O

N=CH2
N=CH2

.
3. - ( ,
).
4. - (, ).

,
, , , , (, ) .
111
(Acidum glutaminicum*)
NH2
CCH2CH2CHC
HO
OH
-
: , , - .,
, .
.
, . , , .
. .
:
COOC2H5
H2C =CH CN
H3COCHNCH
COOC2H5
COOC2H5
89 H3COCHNCCH2CH2C3N
COOC2H5
H 2O
CH3COOH
2C 2H 5OH
COOH
89 H2NCCH2CH2C3N
C O2
COOH
COOH
COOH
H 2O
89 H2NCH
CH2CH2C3N
H2NCH
CH2CH2COOH
. 1. : , .
112
2. ( ).
3. : H2SO4
;
- :
H2CCHC
OH
NH2
H2C
t
H 2O
C
O
O
C
NH
OH
OH
O
C
NH
OH
O
H
HO
H2 SO4;t
H2O
OH HO
OH
O
C
NH
OH
89
HO
NH4OH
OH
OH
89
HO
C
NH2 ONH4
H 2O
OH
O
C
NH2 ONH4
89
HO
113
4. CuSO4:
, - .
. 1. .
9,4 9,55%.
2. , , , = . .:
C
C
O
NH3
OH + NaOH 89
NH3
O
ONa + H O
2
3. , = 1/2. .
. , .
. , , ,
, , .
, , .
(Methioninum)
CH3SCH2CH2CHC
NH2
O
OH
(+,)----
, , , .
. , . , ,
.
. - :
COOC2H5
HCNHCOCH3
HOCH2CH2SCH3
COOC2H5
114
COOC H#
H2O
89 CH!`S`CH `CH `C`NHCOCH!
COOC H#
89 CH!`S`CH `CH `CH`COOH +
NH
+ CO26 + CH3COOH + 2C2H5OH
. 1.
- ( ).
2.
30 %- NaOH :
2 CH3SCH2CH2CHCOOH + 5NaOH
NH2
89 CH3SNa + Na2S + CH3OH + 2NH36 +
+ 2HOCH2CH2CHCOONa
OH
, ,
- .
3. :
Na2S + CH3SNa + 2H2SO4 89
89 H2S6 + CH3SH6 + Na2SO4 + NaHSO4
4. - .
. 1. ( ).
2.
, :
2H3CSCH2CH2CHC
NH2
O
OH
115
+ I2
K 2HPO 4 + KH 2PO 4
NH2
89
SCH2CH2CHCOOH
SCH2CH2CHCOOH
+ 2CH3I
NH2
,
:
I2 + 2Na2S2O3 89 2NaI + Na2S4O6
3. , = . .
4. , , , = 1/2. .:
H3CSCH2CH2CHCOOH + ICl + H2O 89

NH2
89 H3CSCH2CH2CHCOOH + HI + HCl
NH2
ICl + HI 89 I2 + HCl
I2 + 2Na2S2O3 89 2NaI + Na2S4O6
5.
, = . .
. ,
.
. (, , , .), ,
.
(Aminalonum)
Acidum gamma-aminobutyricum*
H2NCH2CH2CH2COOH
-
. , . . , , , .
. -2:
116
COOK
N
H
KOH
C 2H5 OH
COOH
CH3COOH
CH2
C 2H5OH
CH2CH2NH2
CH2
CH2CH2NH2
. 1. .
2. ,
.
3.
- :
O
HN
O
O
OH
O
N
H
O
NH
N
H
NH 3
HN
O
O
NH
N
N
H
O H4NO
N
H
. 1. ,
, , = . .:
COOH
CH2
CH2
+ HClO4
CH3COOH
CH2
NH2
COOH
CH2
CH2
CIO
4
CH2
+
HN H
.
2. .
3. , ,
= . .
. , , ,
.
. . , , .
117
(Cysteinum)
COOH
CHNH2
CH2SH
1--2-
. .
, .
. ( ) :
NH2
SCH2CHCOOH
SCH2CHCOOH
NH2
COOH
[H]
Zn
2 CHNH2
CH2SH
. 1. .
2. (II) ( ).
3. - .
4. (III) , .
5. - ( ).
6. : 9 13 ( 5 %- );
+7 +9 (15 %- 1 ).
. 1. , , = . .:
COOH
2 CHNH2 + I2 89
CH2SH
NH2
SCH2CHCOOH
SCH2CHCOOH
+ 2HI
NH2
2. .
3. , = . .
. , .
. (5 %- ).
118
, .
.
- 10 %-
(Solutio Tetacini calcii 10 % pro injectionibus)
N
CH2
CH2
N
CH2COONa
CH2COO
Ca
CH2COO
CH2COONa
. ; pH = 5,07,0.
. 1. Na+.
2. Ca2+ .
3. , (III)
, .
. .
. (II) , , ,
= . .
. .
. () .
.

()
ROR'.
119
, ;
. , , , .
,
, , .
(Aether medicinalis)
C2H5C2H5

. , , , ,
, .
, . 12 ,
- 95 %- , , , , .
. 135
:
HO
C2H5OH +
HO
+ H2O
O
+ C2H5OH 89 H5C2OC2H5 + H2SO4
S
H5C2O
H5C2O
O
S
89
S
HO
HO

.

(130140 ).

,
:
(CH3COOH, H2SO3 H2SO4, );
( , , , );
(, );
( ).
120
(
)
. ,
.
(! ! ).
:
(Aether pro narcosi),
.
: .

.
.
:
1) ;
2) KI , :
H5C2OOC2H5 + 2KI + H2O 89
89 I2 + H5C2OC2H5 + 2KOH
3) :
CH3C
O
H
+ K2[HgI4] + 3KOH 89
89 Hg5 + CH3COOK + 4KI + 2H2O
1 , .
.
.
. ,
.
. ,
, . .
.
121
(Dimedrolum)
Diphenhydramine hydrochloride*
H5C6
H5C6
CHOCH2 CH2 N
CH3
CH3
HCl
-
.
, , . . , .
. - :
H5C6
H5C6
CHOH + ClCH2CH2 N
89
H5C6
H5C6
CH3
CH3
HCl
CH OCH2 CH2 N
89
H5C6
H5C6
NaOH
CH3
HCl
CH3
CHOCH2CH2N
CH3
CH3
HCl
. 1.
H2SO4 - , -; :
H5C6
H5C6
CHOCH2 CH2N
89
H5C6
H5C6
CH3
CH3
HCl
. H2SO4
CH3
+
CHOCH2CH2NCH3 SO42 + HCl

H
2. (1:9) , 122
, , .
.
3. :
H5C6
H5C6
CH3
CHOCH2CH2N
89
C6H5
C6H5
CH3
HCl
H 2O; HCl; t
CH OH + HOCH2CH2N
CH3
CH3
HCl
, .
(6267 ).
4. .
5. - 230 350
253, 258 264 .
. 1. .
,
() ( )
- , , = . .:
2
H5C6
H5C6
CHOCH2CH2N
+ (CH3COO)2Hg
89 2
H5C6
H5C6
CH3
CH3
HCl + 2HCIO4 +
CH3COOH
CH3
CHOCH2CH2NCH3 ClO4 + HgCl2 +

H
+ 2CH3COOH
.
2. , , , = 1/2. :
H5C6
H5C6
CHOCH2 CH2 N
CH3
CH3
123
HCl + ICl 89
89
H5C6
H5C6
CHOCH2 CH2 N
CH3
CH3
HClICl
Il + KI 89 I2 + KCl
I2 + 2Na2S2O3 89 2NaI + Na2S4O6
.
3. HCl ,
, , = . .
4. HCl ,
= . .
. ,
, .
. () .
, .

.
1 %- (Solutio Nitroglycerini 1 %)
CH2ONO2
CHONO2
CH2ONO2
. 15 , ( ) :
CH2OH
CHOH + 3HNO3
CH2ONO2
H2SO4
CH2OH
CHONO2 + 3H2O
CH2ONO2
124
. 1. ( ):
NO3
NH
NH
89
NO3
H 2SO 4
NH
+
89
HSO4
H
( )
2. ,
.
. 1. ,
( = 410 )
, -2,4-. ,
:
OH
SO3H
OH
KNO 3
O2N
SO3H
3NH4 OH
CH3COOH
SO3H
SO3H
O
89
SO3
(NH4+)3
SO3
2. - H2O2:
C3H5(ONO2)3 + 5NaOH
H 2O2
89 NaNO3 + 2NaNO2 + CH3COONa + HCOONa + 3H2O

125
HCl
, = 1/5. . .
. , , , .
,
180 C :
4C3H5(ONO2)3 89 6N26 + 12CO26 + O26 + 10H2O
!
.
. ()
. ,
.
(Erynitum)
Pentaaerythrityl Tetranitrate*
O2NOH2C
CH2ONO2
C
O2NOH2C
CH2ONO2

. . . , .
.
:
HOH2C
CH2OH
+ 4HNO3
C
HOH2C
CH2OH
H2SO4
O2NOH2C
CH2ONO2
C
89
O2NOH2C
CH2ONO2
+ 4H2O
. 1. (. ).
2. .
99101 .

.
126
( ),
.
. , .
, , .
. ()
.

(Calcium glycerinophosphoricum, Calcii glycerophosphas)
CaPO3OC3H5(OH)2nH2O
CH2 OH
CHOH O
CH2 OPO
OCa
, . - -
. ,
. , , .
.
.
,
.
. 1. a2+ .
2. (II) :
CH2 OH
CHOH O
+ (CH3COO)2Pb 89
CH2 OPO
OCa
CH2OH
89 CHOH O
CH2OPO
OPb
127
+ (CH3COO)2Ca
34.
.
HNO3 ;
PO43 :
H3PO4 + 12(NH4)2MoO4 + 21HNO3 89
89 (NH4)3PO412MoO35 + 21NH4NO3 + 12H2O
. , ,
, = . .
. .
. , , , .
(Phytinum)
,
, :
OPO(OH)2
OPO(OH)
(HO)OPO
OMgO
OPO(OH)2
OPO(OH)
O
Ca
O
OPO(OH)
; , , , , , .
. . , .
. - , HCl.
NH4OH
Na2CO3 . HCl ,
.
. 1.
. Ca2+.
2.
.
. , ,
, = 1/2. . P2O5.
,
CuSO4
:
128
2CuSO4 + 4KI 89 Cu2I2 + 2K2SO4 + I2

I2 + 2Na2S2O3 89 2NaI + Na2S4O6
.
.
. .
. ,
;
, .
(Myelosanum)
Busulfan*
H3CSO2O(CH2)4OSO2CH3
- -1,4
1,4--()-
. . 95 %- , .
. 1.
:
CH3SO2O(CH2)4OSO2CH3
KOH
89 2CH3SO3K5 + HO`(CH2)4`OH
2. .
: 1
,
. 1 ( ).
. , , , = 1/2. .:
HO
CH3SO2O(CH2)4OSO2CH3 t2
89 2CH3SO3H + HO(CH2)4OH
CH3SO3H + NaOH 89 CH3SO3Na + H2O
. , .
,
.
. .
129
RCOR1 .
O
, , , , , , , .
(Aprophenum)
Aprofene*
O
CCOCH2CH2N
CH3
C2H5
C2H5
HCl
- 1,1-

. .
, 95 %- ,
.
.
-.
. 1. Cl.
2. - .

, .
3.
. , , 1 . .
4. ( ).
5. .
6. .
130
7. . KOH .
8.
, .
. 1.
(II) , , , = . .
.
2. (Solutio Apropheni 1 % pro injectionibus)
(Tabulettae Apropheni 0,025) , , ,
= . .
3. , = . .
4. , = . .
. , .
. , .
(Spasmolytinum)
Adiphenine hydrochloride*
O
CHCOCH2CH2N
C2H5
HCl
C2H5
- 1,1-
.
. , .
. 1. :
O
CHCOCH2CH2N
131
C2H5
C2H5
HCl
H 2O; t
89
CHC
O
OH
+ HOCH2CH2N
C2H5
HCl
C2H5
.
2. Cl.
. 1.
(II) , = . .
2. ,
, = . .
3. , = . .
. ,
.
. , .

-)-
-(

, - , , , .
. (
).
:
1. .
2. ():
O=C
OH
OH
89
O=C
OH
NH2
89 O=C
NH2
NH2
()
()
:
132
ROCNH2
O
:
ROH + ClCNH2 89 ROCNH2 + HCl
, , .

, , :
O=C
NH2
NH2
O=C
+ O=CCH2R
H 2O
O=C
OH
NH2
NH2
NH2
NHCCH2R
O
HOOC
HOOC
H 2O
O=C
NH2 COOH
NHC
O
,
():
O=C
NH2
NH2
HOOC
+
HOOC
CH2
2H2O
O=C
NHC
NHC
CH2
O
()

, .

, .
133
(Meprotanum)
Meprobamate*
O
CH2OCNH2
H3CCCH2CH2CH3
CH2OCNH2
O
2--2--1,3
.
, . ,
95 %- .
. :
CH2OH
H3CCCH2CH2CH3 + 2ClCNH2 89
CH2OH
2--2--1,3
CH2OCNH2
89 H3CCCH2CH2CH3 + 2HCl
CH2OCNH2
O
. 1. - .
2. 104108 .
3.
NH3, :
O
CH2OCNH2
H3CCCH2CH2CH3 + 4NaOH
CH2OCNH2
O
134
CH2OH
89 H3CCCH2CH2CH3 + 2NH36 + 2Na2CO3
CH2OH
4. H2SO4 2,
:
O
CH2OCNH2
H3CCCH2CH2CH3 + H2SO4. + 2H2O 89
CH2OCNH2
O
CH2OH
89 H3CCCH2CH2CH3 + 2CO26 + (NH4)2SO4
CH2OH
Ca(OH)2 + CO2 89 CaCO35 + H2O
5.
, 123
125 .
O
O
CH2OCNH2
H3CCCH2CH2CH3 + 2
CH2OCNH2
O
H3CC
H3CC
. H 2SO 4
O
CH2OCNHCOCH3
89 H3CCCH2CH2CH3
CH2OCNHCOCH3
O
135
+ 2CH3COOH
.
( ), , = 1/2. .
.
. . .
. () .
. ,
,
, .
, , , , ,
, , .
.
(Bromisovalum)
Bromisoval*
H3C
CHCHCNHCNH2
H3C
Br
O
O
N-(-)-
. ,
. ,
95 %- .
. - .
H3C
3
O
CHCH2C
OH
H3C
H3 C
H3 C
O
CHCH2C
Cl
H3C
PCl3
H 3PO 3
O
CHCH2C
Cl
H3C
PBr5
89
H2 N
H3C
H3C
O
CHCHC
Br
Br
136
C=O
H2 N
H3C
89
CHCHCNHCNH2
H3C
Br
. 1.
, . :
H3C
CHCHCNHCNH2
H3C
Br
89
H3C
H3C
4NaOH
t
CHCHCOONa + 2NH36 + Na2CO3 + NaBr

OH
HCl, :
C6H5SO2N(Na)Cl + 2HCl 89 C6H5SO2NH2 + Cl2 + NaCl

2NaBr + Cl2 89 Br2 + 2NaCl

.
2. H2SO4 - .
H3C
H3C
CHCHCNHCNH2
Br
89
H 2SO 4; t
2H 2O
H3C
H3C
CHCHCOOH + (NH4)2SO4 + CO26

Br
3. .
CuSO4 137
- ( CuSO4) - :
RCHC NHC NH2
Br
NaOH
t
89 RCHCONa +
OH
H2NCNH2
NaOH; t
H2N
C=O
H2N
NH36 + HN=C=O
HN=C=O + H2NCNH2 89 H2NCNHCNH2 12

O
12 O=CNHCOH
NH2
O
2+
Cu ; NaOH; t
O=CNHCONa
N
H2N
NH
Cu/2
.
(. ), = . .:
NaBr + AgNO3 89 AgBr 5 + NaNO3
3NH4SCN + NH4Fe(SO4)2 89 Fe(SCN)3 + 2(NH4)2SO4
.
. .
. .
-(
-)-
RN
CH2CH2Cl
CH2CH2Cl
R , ,
.
138
-(-)- .
, , , , , .
, .
-(-)- ,
.
. (, )
-
:
RNH2
ClCH2CH2OH
RN
CH2CH2OH
CH2CH2OH
[ (IV) ]:
RN
CH2CH2OH
SOCl2
RN
CH2CH2Cl
CH2CH2Cl
CH2CH2OH
-(-)-. :
RN
CH2CH2 Cl
RN
CH2CH2 Cl
CH2CH2 Cl
HCl
CH2CH2 Cl
,
, -(-)-.
.
-(-)- ;
. (, ), - .
139
-(-)- .
-.
.
, (III)
. -

CCl- - 760770 1
( ).
, , , .
,
.
(Novembichinum)
H3C CH CH2N
CH2CH2Cl
HCl
CH2CH2Cl
Cl
2---(-)-
. , , .
. :
CH3
CH3
CH
CH2
CH3
HCl
H 2C CH 2
O
CHCl
NH
2-
89 CH N
2
SOCl2
CH2CH2OH
CH2CH2OH
2--N-(-)-
CH3
CH3
CHCl
CH2
N
CH2NH2
CHCl
CH2CH2Cl
CHCl
HCl
CH2CH2Cl
2--N-( -)-
140
CH2 N
CH2CH2Cl
CH2CH2Cl
HCl
. 1. (K[BiI4]) .
2. :
Ag+ + Cl
. HNO 3
AgCl 5
. 1.
,
, = . .:
CH3
CHCl
CH2 N
CH2CH2Cl
CH2CH2Cl
HCl + AgNO3 89
CH3
CHCl
89 CH2 N
CH2CH2Cl
HNO3 + AgCl5
CH2CH2Cl
.
AgNO3 + NH4SCN 89 NH4NO3 + AgSCN5
FeNH4(SO4)2 + 3NH4SCN 89 + Fe(SCN)3 + 2(NH4)2SO4

2. ( ), = 1/4. .:
CH3
CHCl
CH2 N
CH2CH2Cl
HCl + 4NaOH
CH2CH2Cl
CH3
CHOH
89 CH2 N
CH2CH2 OH
CH2CH2 OH
+ 4NaCl + H2O
4NaCl + 4AgNO3 89 4AgCl5 + 4NaNO3

141
. , .
. () . , .
(Cyclophosphanum)
Cyclophosphamide*
CH2CH2Cl
NH N
H2O
P
CH2CH2Cl
O O
N--(-)-N,-

. . , 95 %- ,
.
. :
ClCH2CH2
NPOCl2 + HO(CH2 )3 NH2 89
ClCH2CH2
N--(-)-

89
CH2CH2Cl
NH N
P
CH2CH2Cl
O O
Cl
. 1.
.
2. H2SO4 20 %- . ,
.
3. H2SO4
HNO3 .
- , :
H3PO4 + 12(NH4)2MoO4 + 21HNO3 89
89 (NH4)3PO412MoO35 + 21NH4NO3 + 12H2O
.
, = 1/2..:
142
RN
CH2CH2Cl
+ 2NaOH 89 RN
CH2CH2Cl
CH2CH2OH
+ 2NaCl
CH2CH2OH

. , , 10 .
. .
(Sarcolysinum)
Sarcolysin*
NH2
O
HO
CCHCH2
CH2CH2Cl
HCl
CH2CH2Cl
(+,)----[n--(-)-]
. . , , 95 %- , , .
1 : 14 , .
. :
CH2C
O
H
89 O2N
HCN
NH3
CH2CH(NH2)COOH
CH2CH(NH2)COOH
[H]
n-
H 2C CH 2
89 H2N
CH2CH(NH2 )COOH
n-
143
HNO3
COOH
CHNH2
N
89 CH2
CH2CH2OH
SOCl2
CH2CH2OH
(+,)-n--(-)-
COOH
CHNH2
89
CH2
CH2CH2Cl
CH2CH2Cl
HCl
COOH
CHNH2
N
89 CH2
CH2CH2Cl
HCl
CH2CH2Cl
. 1. .
2. ().
3. . ,
1 ,
():
RCH2CH2Cl 89
89 RCH2CH2OH
K2Cr 2O7; t
H SO "
O
H3CC
H
.
, = 1/3. .:
COOH
CHNH2
CH2
CH2CH2Cl
CH2CH2Cl
+ 3AgNO3 + 2H2O
144
COOH
CHNH2
N
89 CH2
CH2CH2OH
+ 3AgCl5 + 2HNO3
CH2CH2OH
FeNH4(SO4)2 + 3NH4SCN 89 Fe(SCN)3 + 2(NH4)2SO4

.
. , .
. . ;
.
(Chlorbutinum)
Chlorambucil*
O
HO
CCH2CH2CH2
CH2CH2Cl
CH2CH2Cl
3-[--(b-)-]
. ,
.
, 95%-
, .
. :
(CH2)3COOH
HNO3
O2N
n-
89 H2N
89
(CH2)3COOH
(CH2)3COOR
HOCH2CH2
HO (CH 2)2 Cl
(CH2)3COOR
HOCH2CH2
n--(-)-
145
SOCl2
[H]
ROH
ClCH2CH2
(CH2)3COOR
89 ClCH2CH2
H2O
n--(-)-
ClCH2CH2
89
ClCH2CH2
(CH2)3COOH
. 1.
AgNO3 .
2.
.
,
1 , (. ).
. 1. .
AgNO3
. AgNO3
, = 1/2. .
.
2. , , = . .
. , ,
.
. .
() .
,
.
( ),
- , ,
.

()

,
.
146

.
(Cyclopropanum)
CH2
H2CCH2
. ,
, .
( 760 . .) 34,50 C. , ,
, ,
. .
. :
ClCH2CH=CH2
HBr
ClCH2CH2CH2Br
Zn
. ,
, , , , .
. , ,
:
H2SO 4
CH3CH2CH2OSO3H
. 99 %
.

6
25 C.
. 12 , , .
, .
. ( )
.
147
(Midantanum)
Amantadine hydrochloride*
NH2HCl
1-
. ,
.
, ,
.
. :
Br2; 100150 C
HBr
Br
NH3
NH2
HBr
HCl
89
NH2HCl
. 1. ,
.
2. 1-
2--1,3.
3. .
.
(II) , ,
, = . .:
NH2HCl + 2HlO4 + Hg(CH3COO)2 89
89 2
H
+
H ClO4 + 2CH3COOH + HgCl2
.
. .
. .
148
(Remantadinum)
Rimantadine hydrochloride*
CHCH3HCl
NH2
--1-
. ,
.
, ,
.
. :
O
HC
CCH3
NH2
CHCH3
O
NHC
H
&'
HCl; H2O
HCOOH
CHCH3HCl
NH2
. 1.

.
2. .
. .
. .
.
, ,
.

.
.
149
(Gludantanum)
COOH
NH
O
H
H
H HO
OH
OH H
1-
. , .
, .
. 1. (
).
2.
.
. ,
, , = . .
.
. , .
. .

(, , .),
.

2--1,3:
H2C=CCH=CH2
CH3
C5H8,
(C5H8)n.
.
.

():
150
CH3
6
5
2
3
CH
9 10
H3C
CH3
, ,
, , .
(Mentholum)
CH3
5
4
3
6
1
OH
CH
H3C
CH3
l-2--5--1
3 ,
23=8 4 .

.

.
.
, .
,
.
, , ,
. , , ,
, .
. 1.
:
)
80 %.
151
, 208212 C,
20 C ;
)
5060 %.
:
OH
B3+ + 3H2O
+ H3BO3 89

,
.
.
2. () ,
.
OH
3. ()
-
:
CH3
ClCH
CH3
CH3
OH
OH
OH
. 1. H2SO4
,
-:
OH
H 2O
152
H2
89
O
H
OCH3
OH
89
HO
89
CH
89
2. 4144 C.
3. : 49 51 (10 %- ).
H2SO4,
HNO3, CH3COOH.
. , .
( ).

NaOH, ,
= . .:
OH
+ (CH3CO)2O 89
O
OCCH3
+ CH3COOH
(CH3CO)2O + H2O 89 2CH3COOH

CH3COOH + NaOH 89 CH3COONa + H2O
.
. , .
. , , , , , ; ,
.
153
(Validolum)
CH3
CH3
CH3
OH
H3C
CH3
OCCH2C
H3C
CH3
H
CH3
2530 %-

. .
, .
.
, ,
.
. 1. H2SO4.
2. 0,894 0,907 /3.
. , .

,
HCl, , = . .:
CH3
OCCH2C
+ KOH
CH3
CH3
89
+ KOOCCH2C
OH
.
H
CH3
KOH + HCl 89 KCl + H2O
.
. , .
. , ,
.
, , .
154
(Terpinum hydratum)
H3C
OH
H2O
H3C
CH3
OH
--1,8-
.
, .
, , , . 100 C,
. .
. , .
25 %- H2SO4, 1014 .
.
CH3
H3C
H3C
OSO3H
HSO 3OH
OSO3H
2H2O
HSO 3OH
2H2SO4
H3C
H3C
OH
OSO3H
CH3
H3C
OH
H 2O
89
H3C
CH3
OH
H2O
H3C
CH3
OH
. 1.
H2SO4
:
155
OH
. H 2SO4
OH
. H2SO4
OH
2.
FeCl3
-, , ,
.
3. 115117 C.
. . , - .
, . , .
. .
.
.

,
.
, , , , , , .
(Camphora)
CH3
O
=
H3C CH3
- , , , , . .
156
d-,
Cinnamomum camphora; l-, , .
. , .
,
. , ,
, . , ,
( ).
. 1. d-
. .
2. l- . . . ,
. (3040 %),
(1020 %), (10 %) . 180 C ,
, NaOH :
OCCH3
OH
H2O; NaOH
[O]
3. .. , . (IV) ,
, :
CH2
HC
TiO 2
OC
OH
O
H
H2O
OH
89
157
[O]
. 1. -
174180 C, 171178 C.
2. 10 %- :
d- +41 +44;
l- 39 44;
1 +1.
3. :
O
+
O
H
O
+
O
H
O
C
89
CH
O
89
CH
4. ( 119,5 C):
NH 2OH
NOH
. .
. ,
.

, , NaOH, , = . .:
O
+ NH2OHHCl 89
NOH
+ HCl
HCl + NaOH 89 NaCl + H2O

.
158
. , .
. ,
, , . .
(Bromcamphora)
CH3
O
Br
. . ,
, , .
. . , ,
:
O
+ Br2 89
+ HBr
Br
. 1. NaOH - :
O
Br
SO2N
Na
Cl
NaOH; Zn
t
+ NaBr + Na2[Zn(OH)4]
+ 2HCl 89
SO2NH2 + NaCl + Cl2
2NaBr + Cl2 89 Br2 + 2NaCl

2. 7476 C.
. 30 %-
159
. 0,1 ,
, = . .:
O
Br
KOH; Zn
t
+ KBr + K2[Zn(OH)4]
Fe(NH4)(SO4)2 + 3NH4SCN 89 Fe(SCN)3 + 2(NH4)2SO4

KBr + AgNO3
HNO 3
AgBr5 + KNO3
Fe(SCN)3 + 3AgNO3 89 3AgSCN5 + Fe(NO3)3

AgNO3, , 0,1 NH4SCN.
. , .
. , ,
.
(Acidum sulfocamphoratum)
CH2SO2OH
O
. . ,
.
. 1.

. -, , BaCl2.
2. 2,4-:
CH2SO2OH
O
+ H2NNH
NO2 89
O2N
160
CH2 SO2OH
89
NNH
NO2
O2N
+ H2O
3. 192195 C,
20 24.
. , , , = . .:
CH2SO2ONa
CH2SO2OH
O
+ NaOH 89
+ H2O

(Sulfocamphocainum 10 % pro injectionibus).
: 49,6 ;

50,4 ;

1 .

= 4,25,8 - . NaOH ,
.

.
. ,
.
. ,

. , .

, , .
1-, 2- 3- :
OH
OH
HO
OH
HO
OH

, . , , -
.
:
OH
ONa
+ NaOH 89
+ H2O

2.
. .
: , , , , , , .
(Phenolum)

(Acidum carbolicum crystallisatum)
OH
. -, -
, , ,
. ,
162
, , , .
. .
. 1. .
2. .
2SO4, , Ca(OH)2, . Na2CO3, NaOH.
H2SO4:
SO2OH
+ H2SO4 89
SO2OH
2
+ H2O
SO3
+ Ca(OH)2 89
Ca2+ + 2H2O
H2SO4 + Ca(OH)2 89 CaSO45 + 2H2O
SO3Na
SO3
Ca2+
2
+ Na2CO3 89 2
SO3Na
+ 2NaOH
ONa
2
+ CaCO35
ONa
+ Na2SO3 + H2O
OH
+ H2SO4 89 2
+ Na2SO4
, ,
178182 C.
. 1. (1:100) FeCl3 - (
). 1 .
:
OFeCl2
OH
+ FeCl3 89
+ HCl
2. ( ):
163
OH
OH
Br
Br
+ 3Br2 89
+ 3HBr
Br
3. .
, :
O
NH 3
[O]
OH
O
C $H #OH
NH
OH
4. .
- :
+
ONa
ONa
N3N
Cl 89
N=N
SO!H
SO3H
, , -
, , -.
. , .

KBrO3, KBr, H2SO4, 1015 :
KBrO3 + 5KBr + 3H2SO4 89 3K2SO4 + 3Br2 + 3H2O
OH
OH
Br
Br
+ 3Br2 89
+ 3HBr
Br
164
KBrO3 , , , = 1/6M. .:
Br2 + 2KI 89 I2 + 2KBr
I2 + 2Na2S2O3 89 2NaI + Na2S4O6
.
. , .
. . .
35 %- , 2 % ,
( ) ,
.
(Thymolum)
CH3
OH
H3CCHCH3
2--5-
. , - . , , , . .
. -:
OH
OCOCH3
(CH3CO)2 O
CH3
CH3
O
CH3C CH 3; t
H 2O
CH3
CH3
[H 2]; Ni
89
OH
H3CCH=CH2
--
165
OH
H3CCHCH3
. , ( FeCl3),
:
) 3
H2SO4 HNO3
- - ,
;
) NaOH - , -.
. , , , = 1/4. .
NaOH, KBr,
HCl 0,1 KBrO3
:
KBrO3 + 5KBr + 6HCl 89 3Br2 + 6KCl + 3H2O
CH3
Br
OH
H3CCHCH3
+ 2Br2 89
CH3
Br
+ 2HBr
OH
H3CCHCH3
. , .
. , .
, .
(Resorcinum)
HO
OH
-
. , , . .
, , , , .
.
.
:
166
SO2OH
H2SO4
SO3H
H2SO4
NaOH
.
SO3H
OH
ONa
H+
89
ONa
OH
. .

H2SO4 , - :
O
C
C
O
H
HO
. H2SO4
2H2O
C
O
OH HO
OH HO
NaOH; H 2O
OH
O
89
C
HO
CONa
OH
COONa
C
NaOH
2H 2O
OH
NaO
. .
. , ,
= 1/6. . (. ).
. .
. .
5,
10, 20 % 2,5 %- - .
167
(Phenolphtaleinum)
HO
OH
C
O
C
O
,--(4-)-
.
, . ,
.
.
:
OH
OH
H O H
C
C
OH
. H2SO 4
OH
H 2O
C
O
. , :
OH
OH
OH
OH
C
O
C
OH
OH
C
OH
COO
O
H
168
H 2O
COO

- = 8,210,0.
( > 12,0)
.
. ( ):
OH
HO
O
2H2O
H O H
C
C
C
O
C
O

.
. . I2,
. HCl, , , :
OH
OH
NaO
6NaOH; 4I
C
O
COONa
4NaI; 6H O
2HCl
2NaCl
C
O
I
89
OH
I
C
O
C
O
169
OH
. .
.
, . .
(Xeroformium)
Br
Br
Br
BrBi2O3
OBiO
OH Br
Br

.
. , , .
.
. :
Br
OH
Br
NaBr
Cl2; 20 C
Br
Br
NaOH
H2O
OH
Br
Br
ONa
2,4,6-
2,4,6-
Br
2
Br
Br
+ 3Bi(NO3)3 + 4H2O 89
10 %-
ONa
Br
89 Br
Br
OBiO
Br
OH
BrBi O! 5 + 2NaNO3 + 7HNO3
Br
. 1. Bi3+:
2Bi3+ + 3S2 89 Bi2S35
170
2. ,
, .
. HNO3 HClO4, , = 1/2. . Bi2O3.
. , .
. , .
, .
(Oxolinum)
O
O
O
2H2O
O
1,2,3,4--1,2,3,4-
. ,
. . , .
. 30 %- .
. , ,
.

,
, .
(). ,
.
NHCOCH3
171
, , , -.
, - .
-
.

.
(Paracetamolum)
Paracetamol*
NHCOCH3
OH
-
. . , .
.
.
. -
-, :
NH2
NO
(CH 3CO)2O
H2S; NH3
NaNO 2
CH3COOH
H2SO4
OH
NHCOCH3
OH
OH
OH
. 1. FeCl3 -
:
NHCOCH3
NHCOCH3
+ FeCl3 89
+ HCl
OFeCl2
OH
172
2. K2Cr2O7 - :
NH2
NH2
NHCOCH3
NH
OH
[O]
H+; Cr2O72
OH
NH2
OH
3.

:
+
OH
ONa
N3N
Cl
NHCOCH3
N=N
2NaOH
NHCOCH3
R +
+NaCl + 2H2O
4. ,
,
:
H O; t
HCl
OH
NH2
NHCOCH3
N3N
NaNO
HCl
OH
OH
Cl
NaOH
ONa
OH
N=N
89
ONa
. -
.
. (
), , :
173
NH2
NHCOCH3
HCl; t
CH !COOH
N3N
NaNO
HCl; KBr
OH
OH
Cl
OH
:
2NaNO2+2KI + 4HCl 89 I2 + 2NO6+ 2KCl + 2NaCl +2H2O
.
. , .
. .
(Phenacetinum)
Phenacetin*
OC2H5
NHCOCH3
1--4-
. ,
. ,
, 95 %- .
. -,
-.
(- ). -
. :
NO2
NO2
HNO3
C2 H5 Br
NH2
[H]
NHCOCH3
(CH3CO)2 O
H2SO4
OH
OH
OC2H5
174
OC2H5
OC2H5
. 1.
. -. K2Cr2O7 ( ) - :
OC2H5
H5C2O
NHCCH3
HCl; H 2O
H2N
+
2 H5C2O
NH2
+ CH3COOH
H ; Cr 2O 7
OC2H5
89 H5C2O
H 2N
NH
O C 2 H5
2
Cr2 O7 ; H
H2N
OC2H5
89
H5C2O
N=
=N
OC2H5
H2N

2. HNO3
, 3--4-:
NHCOCH3
HNO3
NHCOCH3
NO2
OC2H5
OC2H5
. -,
-, .
175
.
, , -00
, = . .:
NHCOCH3
NH2
HCl; t
CH3COOH
N3N
NaNO2
Cl
HCl
OC2H5
OC2H5
OC2H5
.
. . .
. .
, .
, , , .
(Xycainum)
(Lidocainum)
H3C
CH3
NHCCH N
HCl
O
-2,6-
. . , ,
.
. 2,6-
,
. 2,6-
:
ClCH2COCl
H3C
NH2
CH3
2,6-
HCl
(C 2H5 )2NH
H3C
CH3
NHCOCH2Cl
2,6-
176
HCl
HCl
89
H3C
CH3
NHCOCH2N(C2H5 )2
. 1. Cl.
2.
2,6-, (. ).
. 1. ,
(II) , = . .
2. , = . .
3. , = . .
4. , = . .
. , .
. . ,
. . , .
(Trimecainum)
Trimecaine hydrochloride*
CH3
H3C
CH3
NHCCH N
HCl
O
-2,4,6-
. .
, , .
. :
CH3
CH3
(C 2H5 )2NH
ClCH2COCl
H3C
NH2
CH3
2,4,6-
HCl
H3C
CH3
NHCOCH2Cl
2,4,6-
177
HCl
CH3
89
HCl
H3C
CH3
NHCOCH2N(C2H5)2
. 1. Cl.
2. ( ) ,
NH2-:
CH3
CH!
NaNO 2
H2O; t
H!C
CH!
NHCOCH N(C H# )
NaOH
H3C
CH3
H3C
CH3
N
3N
+
NaOH
HCl
CH3
OH
Cl
89
NH2
CH3
CH3
N=N
NaO
H3C
. 1. ,
(II) , = . .
2. , = . .
3. , = . .
4. , = . .
. ,
.
. .
.
178

,
.

, .
, , , .

, .

.
(Acidum benzoicum)
COOH
. . .
, , , , . .
.
() Resina Benze 1608 .
:
1. :
CH3
+ 3MnO2 + 3H2SO4 89
COOH
+ 3MnSO4 + 4H2O

2. :
CH3
3Cl2
3HCl
CCl3
C(OH)3
3H2 O
H 2O
3HCl
179
COOH
3. :
COO
COOH
2
COOH
Ca
+ 2Ca(OH)2 89 2
COO
COO
Ca2+
89 2CaCO3 +
330350 C
HCl
COOH
2
+ CaCl2
. 1. (III) . NaOH ( ). (III)

- (III) :
COONa
6
+ 2FeCl3 + 10H2O 89
89
O
Fe3+Fe(OH)37H2O + 3
COOH
+
+ 6NaCl
2. .
. ,
, , = . .:
COOH
COONa
+ NaOH 89
+ H 2O
. .
.
.
(Natrii benzoas, Natrium benzoicum)
COONa
.
, - .
, .
180
. :
COOH
2
COONa
+ Na2CO3 89 2
+ H2O + CO26
. 1. Na+
.
2. FeCl3 (. ).
. , ,

, , = . .:
O
ONa
+ HCl 89
O
OH
+ NaCl
. .
. .
(15 %- ) ,
.
. ,
(), ,
, . , , .
C6H5COOH + H2NCH2COOH 89
89 C6H5CNHCH2COOH + H2O

.
, . , ,
181
(, )
( ),
, , .
(Acidum salicylicum)
COOH
OH
-
. .
. .
, , , , .
. , . 125 C.
:
ONa
OH
CO2; t
OH
COONa
COOH
HCl
(250300 C)
-.
. 1. FeCl3 - ,
HCl
CH3COOH:
O
CO
OH + FeCl3 89
OH
FeCl + 2HCl
2. 160
().
,
( ):
182
OH
OH
OH
+ CO26
3.
( ):
COOH
+
COOH
OH
H H
HO
HO
89
H2 O
COOH
. H2SO4
COOH
COOH
OH
HO
[O]
COOH
O
.
:
OH
,
, ,
, , .
. 1. , , . , ,
NaOH , = . .:
C
OH
O
OH
COONa
+ NaOH 89
OH
+ H2O
2. , , ,
= 1/6. .:
183
KBrO3 + 5KBr + 3H2SO4 89 3Br2 + 3K2SO4 + 3H2O
COOH
OH
Br
Br
+ 3Br2 89
OH
+ 3HBr + CO26
Br
2KI + Br2 89 I2 + 2KBr
I2 + 2Na2S2O3 89 2NaI + Na2S4O6
. , .
. , ,
.
.
, , , .
.
.
(Natrii salicylas, Natrium salicylicum)
COONa
OH
. ,
, - . ,
, , .
. :
COOH
OH
COONa
+ NaHCO3 89
OH
+ CO26 + H2O
. 1. Na+ .
2. FeCl3 (. ).
3. , .
184
. 1. (. ),
= . .
2. , .
. , ,
.
. , .
(Acidum acetylsalicylicum)
(Aspyrinum)
O
OH
OCCH3
O

. , .
,
. , , , , .
. 1.
:
OH
CH3C
O
+
CH
C
3
COOH
O
H2SO4
.
O
OH
+ CH3COOH
OCCH3
2.
:
OH
3
COOH
+ 3 CH3COOH + PCl3
185
50 C
C
89 3
OH
OCCH3
+ H3PO3 + 3HCl6
O
3. :
OH
COOH
+ CH2 =C=O 89
O
OH
OCCH3
O
. 1. :
COOH
COONa
3NaOH
OCOCH3
+ CH3COONa + 2H2O
ONa
COONa
COOH
H2SO4
+ Na2SO4
OH
ONa
t = 156161 C
,
: -
, :
CH3COOH + C2H5OH
H2SO4
.
CH3C
O
OC2H5
+ H 2O
, ,
(III)
.
186
2. . .
, ( ).
3.
, ,
-, -, -,
HCl :
C
2
O
OH
OCCH3
+ 2Ca(OH)2
C
89
O
O
OH
t
(CH3COO)2Ca
Ca2+ + (CH3COO)2Ca + 2H2O

2
CH3CCH3 + CaO + CO26

O
NO
H3CCCH3 +
C
O 89
H
NO
NO
CH2CCH3 89
OH
CH2CCH3
OH
C
C=C
. 1. , ,
, = . .:
COOH
+ NaOH
20 C
OCOCH3
COONa
OCOCH3
187
+ H 2O
20 C .
2. -, , ( ),
= 1/2. .
.
3. (. ).
. .
. , , , ,
, , ,
.
. ,
, , .
. , , , , .
(Phenylii salicylas, Phenylium salicylicum)
(Salolum)
OH
COOC6H5

- . . 1886 .
. , ,
,
, . ,
, , ,
, . .
.
. , , , .
188
.
:
OH
ONa
+ 2
+ POCl3 89
COONa
OH
89 2
+ NaPO3 + 3NaCl
COOC6H5
. 1.
FeCl3 ,
(III) .
2.

:
O
O
+ H 2O
H SO "
OH
OH
OH +
OH
,
(. ).
. 1. ,
:
OH
+ 3NaOH
ONa
ONa
+
COONa
COOC6H5
+ 2H2O

:
OH
ONa
+ HCl 89
+ NaCl
COONa
COONa
ONa
OH
+ HCl 89
189
+ NaCl
, .
, 1 / , , = . .
.
2. , = 1/12 . .
. , .
.
(, ), , , .
. , , .
(Salicylamidum)
Salicylamide*
O
CNH2
OH

. . . , , 95 %- , .
.
:
COCH3
CNH2
25 %- NH3
OH
OH
+ CH3OH
. 1. FeCl3 - .
2. :
O
Br
CNH2
OH
CNH2
+ 2Br2 89
+ 2HBr
OH
Br
190
3. NH3
30 %-
:
O
CNH2
CONa
NaOH; t
+ NH36
OH
OH
. , = ..
. , , H3BO3 -
.
H3BO3 + NH3 89NH4BO2 + H2O
4H3BO3 + 2NH3 89 (NH4)2B4O7 + 5H2O
NH4BO2 + HCl + H2O 89H3BO3 + NH4Cl
(NH4)2B4O7 + 2HCl + 5H2O 89 4H3BO3 + 2NH4Cl
.
. ,
.
. , .
,
.
.
(xaphenamidum)
Osalmid*
CN
OH
OH
-
. , -
. , 95 %-
, .
191
. :
O
COC6H5
OH
CN
OH
+
OH
NH2
OH
OH
n-
. 1. :
CN
OH
NH2
COH
HCl; t
OH
OH
OH
n-
n- - :
NH
NH2
ONa
+
ONa
ONa
89
ONa
ONa
HCl
NaOH
ONa

N
12
OH
OH

, .
192
2. FeCl3.
. , = . (. ).
. ,
.
. . ,
.
(Dermatolum, Bismuthum subgallicum)
HO
HO
COBi
OH
OH
HO

-3,4,5-
. ,
.
, 95 %- ,
, ,
, .
. . 3040 C :
HO
Bi(NO3)3 + HO
HO
COOH + 2H2O 89
HO
89 HO
COOBi
OH
OH
+ 3HNO3
HO
. 1. Na2S - :
193
HO
2 HO
HO
COOBi
OH
+ 3Na2S + 6HCl 89
OH
HO
89 Bi2S35 + 2 HO
COOH + 4H2O + 6NaCl
HO
2. ,
H2S FeCl3 -
( ).
. HNO3 HClO4,
,
= 1/2. . Bi2O3.
. , .
. , (, , ) , , .

n-
, . - ( H1) :
NH2
COOH
,
, , , .
194
- , .
:
CH2
CHCHC
HC3N
CH2
CH
CHCH2
O
OCH3
OCC6H5
O
,
.
.

, , .
,
( ),
:
N(C)nXCOAr ,
X = O, S, NH.
, (, .).
(Anaesthesinum)
Benzocaine*
NH2
COOC2H5
-
. , . . 195
, , , , .
. :
NO2
NO2
HNO 3
K2 Cr2 O7
C2 H5OH
H 2SO 4
H2 SO 4
H2SO4
CH3
CH3
n-
O
OH
n-
NH2
NO2
Fe; CH3COOH
89
COOC2H5
OC2H5

n-
. 1. :
+
N3N
NH2
NaNO2
Cl
HCl
O
OR
HO
O
OR
N
N
NaO
89
O
OR

196
2. :
CH3
NH2
O
+
N=CH
CH3
N
CH3
N
CH3
H 2O
OR
OR
3. ,
:
NH2
NH2
NaOH; t
+ C2H5OH
COOC2H5
COONa
C2H5OH + 4I2 + 6NaOH 89 CHI35 + 5NaI + HCOONa + 5H2O
4.
HCl .
. 1. , , = . .:
+
N3N
NH2
NaNO2
Cl
HCl; KBr
OR
O
OR
2NaNO2 + 2KI + 4HCl 89 I2 + 2NO6 + 2H2O + 2KCl + 2NaCl

.

-00
.
2. , , = 1/4. .:
197
NH2
Br
NH2
Br
+ 2Br2 89
+ 2HBr
COOC2H5
COOC2H5
Br2 + 2KI 89 I2 + 2KBr
I2 + 2Na2S2O3 89 2NaI + Na2S4O6

3. , , = 1/4. .:
NH2
NH2
+ 2ICl 89
COOC2H5
+ 2HCl
COOC2H5
ICl + KI 89 I2 + KCl
I2 + 2Na2S2O3 89 2NaI + Na2S4O6

. , .
. 510 %
, ,
. .
520 %- . ,
, .
(Novocainum)
Procaine hydrochloride*
O
H 2N
CO CH2CH2N
C2H5
HCl
C2H5
- -

. , . 198
. , ,
, .
. 1.
-
:
C 2H 5
HOCH2 CH2 N
H2N
COOC2H5
C 2H 5
C 2H5ONa
89 H2N
COOCH2CH2N

89 H2N
C2H5
HCl
C2H5
C2H5
COOCH2CH2N
C2H5
HCl
2. ,
-:
O2N
CH3
K 2Cr2 O7
H2 SO4
n-
n-
89 O2N
n-
89
COOCH2CH2N
-
n-
89
H2N
OH
C 2H 5
C 2H 5
Cl
-
n-
H2N
SOCl2
HO CH2 CH 2 N
COOCH2CH2N
O2N
89
O2N
C2H5
C2H5
Fe
CH3COOH
C2H5
C2H5
HCl
C2H5
COOCH2CH2N
HCl
C
H
2 5
199
. 1. .
2. -.
3. KMnO4. , , 0,1
( ).
4. .
.
5.
:
H2N
89 H2N
C2H5
COOCH2CH2N
HCl + NaOH 89
C2H5
COOCH2CH2N
C2H5
C2H5
+ NaCl + H2O
. 1. (. ), = . .
2. . , ,
, , = . .
3. ,
= . .
. .
. .

.
. . , .
, - . n-
(), , , .
.
. , .
200
(Novocainamidum)
Procainamid hydrochloride*
O
CNHCH2CH2N
H 2N
C2H5
HCl
C2H5
- -
. , . , , ,
.
. :
C 2H 5
O2N
n-
C 2H 5
Cl
CONHCH2CH2N
89 O2N
- n -
89 H2N
CONHCH2CH2N
- n-
89 H N
2
C2H5
Ni Raney
C2H5
C2H5
HCl
C2H5
CONHCH2 CH2N
C2H5
HCl
C2H5
. 1. .
2. -.
3. .
NH4VO3,
- (
).
. .
. .
201
. .
; :
O
NH
, ,
. ,

.
(Dicainum)
Tetracaini hydrochloridum*
O
H9C4NH
CH3
COCH2CH2N
HCl
CH3
-
-
. .
, , .
. :
H2N
COOH
C 4H9Br
H9C4NH
COOH
SOCl2
n-
CH3
O
89 H9C4NH
HOCH2CH2 N
CH3
-
Cl
n-
O
89 H9C4NH
CH3
COCH2 CH2 N
-
n-
202
CH3
HCl
CH3
COCH2CH2N
HCl
CH3
89 H9C4NH
. 1.
:
CH3
COO(CH2)2N
COONa
HCl
CH3
+ 2NaOH
NHC4H9
NHC4H9
CH3
+ HO(CH2)2N
CH3
+ NaCl + H2O
-
, :
COONa
COOH
COOH
HCl
NaCl
NHC4H9
HCl
Cl
+
NH2C4H9
NHC4H9
N-
:
COOH
COOH
Cl
NaNO 2
+ H2O
HCl
NH2C4H9
ONNC4H9
2. -.
203
3.
- - - :
O
H9C4NH
CH3
CO(CH2)2N
HNO3; t
HCl
CH3
89 H9C4NH
CH3
CO(CH2)2N
N
+
CH3
HNO3
KOH
C2H5 OH
OK
89 H9C4N
O
CO(CH2)2N
N
+
CH3
CH3
.
, = . .:
ONNC4H9
HNC4H9
NaNO 2
HCl; KBr
. .
. .
, 2
10 .

-
n- () .
204
1946 . ,
, . . -
, , . OH-
.
.
, . N- () , .
- (Natrii para-aminosalicylas)
C
H2N
OH
O
ONa 2H O
2
-
. , .
.
, . Na-
80 C, .
. - ,
, n-
:
OH
NO2
-
OH
[H]
COOH
OH
CO2
NaHCO 3
NH2
NH2
-
COONa
OH
n-
NH2
-
. 1. :
205
COONa
OH
COOH
OH
NaNO 2
OH
Cl
HCl
NaOH
N3N
NH2
ONa
89
N0N
ONa
O
ONa
2. FeCl3 - .
3. Na+
.
4. -;
.
.
- ( ),

n-. :
+
N3N
HO
OH
Cl 89
+
NO2
NO2
NO2 NH2
. 1.
( ), = . .
2. , , = . .
3. , = 1/4. .
4. (. ).
. , .
. .
:
.
206
(Bepascum)
Calcii Benzamidosalicylas*
COO
O
C6H5CNH
OH
Ca2+5H2O
2
-
. , .
,
95 %- ,
.
. :
COONa
OH
C 6H 5 C
COONa
OH
CaCl2
Cl
NHC
NH2
n-
O
OC6H5
n-
89
COO
O
C6H5CNH
OH
Ca2+5H2O
2
. 1.

.
2. FeCl3 .
. . , HCl .
NaOH , = . .
. , .
. .
207
-
()

N- :
5
4
1
2
OH 2
NH
4
6
.
(Acidum mefenaminicum)
O
OH
NH
H3C
CH3
N-(2',3'-)-
(Mefenaminum natrium)
O
ONa
NH
H3C
CH3
N-(2',3'-)-
. () - , .
, ,
.
- . , .
. 1. - 1 .
208
2. -.
3. -
- .
4. .
. .
, , ,
= . .:
COOH
NH
COONa
+ NaOH 89
H3C
NH
CH3
H3C
+ H 2O
CH3

.
. .
. , , .
,
.

N- N-.
, ,
-.
- (Diclofenac-Natrium)
CH2C
Cl
O
ONa
NH
Cl
2-(2',6'-)-
. , ,
.
209
SO2OH
SO2NH2
(I) (II):
SO2N
Cl
R
O
R
SO2NHCNHR
I.
II.
R=H, COOH
R= CH3, Cl, NH2
R'=Na, Cl
R'= C4H9, C3H7
,

.
(Chloraminum )
SO2N
Cl
3H2O
Na
N--,
.
. ,
.
210
. , .
, .
HOSO 2Cl
SO2Cl
NH3
SO2NH2
NaClO
SO2N
89
Cl
Na

, ,

:
NaClO + H2O 89 NaOH + HClO
SO2NH2 + NaOH 89
SO2N
Na
H
+ H2O
. 1. .
( ):
SO2N
Cl
Na
+ H2O 89
SO2NH2 + NaClO
NaClO + H2O 89 NaOH + HClO

2HClO 89 2HCl + O26

( ),
(
).
2. .
(Na+).
3.
:
211
SO2N
Cl
+ HCl 89
Na
SO2NH2 + Cl26 + NaCl

.
:
Cl2 + 2KI 89 I2 + 2KCl
. , , , = 1/2. . Cl2. (.
). . , ,
:
I2 + 2Na2S2O3 89 2NaI + Na2S4O6
2529 % .
. , .
. .
, (0,250,5 %-
), ,
(13 %- ),
, (1,5
2 % - ).
(Pantocidum)
SO2N
Cl
HO
Cl
N---
. .
,
.
. 1.
( ), (
).
2. :
212
O
HO
SO2N
89
Cl
Cl
+ 2HCl 89
HO
SO2N
H
H
+ 2Cl26

(. ).
. , , .
,
. , , , = 1/2. . Cl2:
2NaOOC
SO2N
Cl
Cl
+ 8KI + 3H2SO4 89
89 4I2 + Na2SO4 + 4KCl +

+ 2HOOC
SO2N
H
H
+ 2K2SO4
I2 + 2Na2S2O3 89 2NaI + Na2S4O6

50 %.
. , ,
.
. . ,
, , ,
, .

,
II .
213
(Butamidum)
Tolbutamide*
H3C
SO2NHCNHC4H9
O
N-(-)-N'-
. , . ,
95 %- , , .
. :
HOSO 2Cl
H3C
H3C
NH3
SO2 Cl
n-
89 H3C
SO2NH2
NaOH
C 2H 5OH
n-
89 H3C
SO2N
n--
Na
H
C 4H9N =C =O
Na O
89 H3C
SO2NCNHC4H9
HCl
O
89 H3C
SO2NHCNHC4H9
. 1. 30 %-
,
. :
H3C
SO2NHCNHC4H9 + 3KOH 89
O
214
89 H3C
SO2OK + C4H9NH2 + NH36 + K2CO3
2. 50 %-
( )
- 135138 C:
H3C
SO2NHCNHC4H9
H2 O
H2 SO4
O
89 H3C
SO2NH25 + CO26 + C4H9NH2
3.
, .
-.
4. -
. , 0,001 %-
0,01 227 .
405435.
. , , , = . . , . :
H3C
SO2NHCNHC4H9 + NaOH 89
O
89 H3C
SO2NCNHC4H9 + H2O
Na O
. , .
. .
215
(Chlorpropamidum)
O
Cl
SO2NHCNHC3H7
N-(-)-N'-
. .
, , ,
, , .
. :
O
Cl
SO2NH2
H 2N C NH 2
NaOH
n-
O
89 Cl
SO2NHCNH2
H 2SO 4
CH3OH
n-
89 Cl
SO2NHCOOCH3
C 3H 7NH 2
N-n-
O
89 Cl
SO2NHCNHC3H7
. 1.
, :
O
Cl
SO2NHCNHC3H7 + 3NaOH 89
89 Cl
SO2ONa + C3H7NH2 + NH36 + Na2CO3

216
2.
. - -:
HCl
SO42 + Ba2+
Cl + Ag+
BaSO45
HNO3
AgCl5
3. 50 %- ( ) n-
143144 C:
O
Cl
SO2NHCNHC3H7
89 Cl
H2 O
H2 SO4
SO2NH25 + CO26 + C3H7NH2
. , , , , = . .:
O
SO2NHCNHC3H7 + NaOH 89
Cl
Na O
89 Cl
SO2NCNHC3H7 + H2O
. .
. .
(Bucarbanum)
Carbutamide*
O
H2N
SO2NHCNHC4H9
N-(-)-N'-
. .
217
(Glibenclamidum)
Maninil*, Daonil*
H3CO
CN(CH2)2
SO2NHCN
Cl
N-[4-[2-(5--2-)-]-]N'-
. ( ),
.
(Predianum)
O
H3C
SO2NHCNHN
1-(3-[3,3,0]--3-)-3-(-)-
. ;
, .

( )
,

RHN
SO2NHR'
. 1. :
H 2N
SO2OH
NaOH
H2N
SO2 ONa
n-
218
(CH 3CO)2O
PCl5
SO2ONa
89 CH3CONH
n-
R NH 2
SO2Cl
89 CH3CONH
n-N-
H2SO4
SO2NHR
89 CH3CONH
HOH
R- n-N-
SO2NHR
89 H2N
R-
2. N-:
HOSO2Cl
H3COCNH
O
89 H3COCNH
SO2Cl
R NH 2
n-
89
H3COCNH
SO2NHR
NaOH
O
R- n-
89 H2N
SO2NHR
. 1. .
. , :
RHNO2S
NH2HCl
.
219
, .

:
Na
H2N
SO2NHR
NaOH(Na2CO3)
H2N
SO2NR

(R). , .
, :
NH
H2N
SO2NHCNH2
2. , , :
Br
H2N
SO2NHR
2Br2
SO2NHR + 2HBr
H2N
Br
3.

. - - .
+
NH2
N3N
NaNO2
Cl
HCl
SO2NHR
HO
NaOH
SO2NHR
N
NaO
89
SO2NHR
, ( , . .).
.
220
4.
10- .
SO42 :
H2N
SO2NHR
. HNO3
89 H2SO4 + CO26 + NH4NO3 + NO6 + NO26 + H2O

H2SO4 + BaCl2 89 BaSO45 + 2HCl
5.
(CuSO4, CoCl2, FeCl3).
, . 0,1
, .
,
.
:
H2N
Na
2 H2N
SO2NR
SO2NR
CuSO4
Cu
Na2SO 4
SO2NR
H2N
6. 1 %-
- .
7. ()

. .
8. . -.
,

1 - . ,
:
H2N
SO2NHR +
O
H
C
221
H
H 2O
CH=N
89
SO2NHR
9. -.
. 1.
.
20 C, , = . .:
H2N
SO2NHR
NaNO 2; HCl
N3N
KBr
SO2NHR Cl
2. . . , = . .:
Na
H 2N
SO2NHR
NaOH
H2O
H2N
SO2NR
,
.
, (). = 107108 ()
- .
= 109 (, )
(, ). , , .
3. . - , , = . .:
Na
H2N
SO2NR
HCl
NaCl
H2N
SO2NHR
4. .
.
222
. ,
, = 1/4. .:
KBrO3 + 5KBr + 3H2SO4 89 3Br2 + 3K2SO4 + 3H2O
NH2
NH2
Br
Br
+ 2Br2 89
+ 2HBr
R
Br2 + 2KI 89 I2 + 2KBr
I2 + 2Na2S2O3 89 2NaI + Na2S4O6

5. . ,
, = 1/4. .:
NH2
NH2
+ 2ICl 89
+ 2HCl
I2 + 2Na2S2O3 89 2NaI + Na2S4O6
6. .
(, ).
NH2
NH2
+ AgNO3 89
N
SO2NH
+ HNO3
Ag N
SO2`N
2HNO3 + Na2B4O7 + 5H2O 89 4H3BO3 + 2NaNO3

, , , ( ),
= . .
223
7. . .
8. .
. , , , , , .
. , ,

, n- .
.
. .
(Streptocidum)
Sulfanilamide*
H2N
SO2NH2
-
. . , ,
, ,
, .
. 1. :
H 2N
SO2NH2 + NaOH
89 H2N
SO2ONa + NH36
2.
.
3. - ,
.
4. , (III)
- .
.
, .
. .
224
(Streptocidum solubile)
NaO3SCH2NH
SO2NH2
-
. . ,
.
. 1. (
-
).
2. (Na+).
3.
( ).
,
:
NHCH2SO3Na
NH2
O
H2 SO4; t
+ NaHSO4 + HC
SO2NH2
O
+ HC
OH
HOOC
89
+ SO26
SO2NH2
COOH
2
CH2
HO
COOH
[O]
OH
HOOC
89
CH
HO
COOH
O
2KIO3 + 5SO2 89 I2 + 4SO3 + K2SO4

. . , :
Na2SO3 + I2 + H2O 89 2NaI + H2SO4
225
. .
. .
- (Sulfacylum-natrium)
Sulfacetamidum natricum*
(Albucid-natrium)
Na O
H2N
SO2NCCH3H2O
-
. .
, , , , .
. 1. .
2. (
Na+).
3. - , .
4. , :
Na O
H2N
SO2NCCH3
89 H2N
C 2H5OH
H2SO4
SO2NH2 + CH3COOC2H5 + NaHSO4
. , .
. , .
(Sulginum)
Sulfaguanidine*
NH
H2N
SO2NHCNH2H2O
-
. .
,
226
.
, .
. 1. - ,
( ,
):
2NH=CNH2
NH=CNHC=NH + NH36
NHR
NHR
NHR
2. , , .
0,1
23 .
3. :
NH
H2N
SO2NHCNH2 + H2O + 3NaOH

89 H2N
SO3Na + 3NH36 + Na2CO3
4. .
.
, .
. .
(Urosulfanum)
Sulfacarbamide*
O
H2N
SO2NHCNH2H2O
-
. ,
. , , , , .
. 1. - , ( ).
227
2. :
O
H2N
SO2NHCNH2 + 3NaOH
89 H2N
SO3Na + 2NH36 + Na2CO3
3. 5 %- - (
).
4. .
. .
. .
(Norsulfazolum)
Sulfathiazole*
H2N
N
SO2NH
S
2-(-)-
- (Norsulfazolum-natrium)
Sulfathiazolum natrium*
Na
H2N
N
SO2N
S
2-(-)-
. ,
. , , ,
, , .
- , ,
.
.
. 1.
- .
2. ,
-.
228
3. - ,
( ),
, () .
4. .
5. ( Na+).
. .
. , .
(Aethazolum)
Sulfaethidole*
H2N
N
SO2NH
N
S
C2H5
2-(-)-5--1,3,4-
- (Aethazolum-natrium)
Sulfaethidolum natrium*
Na
H2N
N
SO2 N
N
S
C2H5
2-(-)-5--1,3,4-
. ,
, . , , ,
, .
- .
, , .
. 1. - , .
2. .
3. - ,
( ).
4. .
.
.
. , .
229
(Sulfadimezinum)
Sulfadimidine*
CH3
H2N
SO2`NH
N
N
CH3
2-(-)-4,6-
. , . , ; , .
. 1.
- , .
2.
.
3. .
.
.
. , .
(Phthalazolum)
Phthalylsulfathiazole*
COOH
N
SO2NH
CONH
S
2-[-(-)-]-
. , .
, , ,
.
. 1. ( ).
2. .
3. ,
230
. - :
CO
OH
+
COOH
. H 2SO 4
NaOH; H2O
HO
COOH
OH
OH
C
89
HO
COONa
COONa
OH
NaOH
NaO
OH
. 1.
.
2. .
. ,
, = 1/2. . ,
,
:
COOH
CONH
N
SO2NH
COONa
89
CONH
+ 2NaOH
HCON(CH 3)2
Na
N
SO2N
+ 2H2O
, 1,58 (
).
. .
231
. . , .
.
(Sulfadimethoxinum)
Sulfadimethoxine*
OCH3
H2N
SO2NH
N
OCH3
6-(-)-2,4-
. ,
.
, , .
. 1.
- .
2. -
.
3. .
. .
. .
. .
(Sulfalenum)
Sulfalene*
H2N
SO2NH
N
N
H3CO
2-(-)-3-
. , .
232
,
.
. 1. 310 340 325 2 .
.
2. -
275 310 289 2 . .
3. .
4. - , -.
. ().
. .
. .
. .
65 . , .
(Sulfazinum)
Sulfadiazine*
H2N
SO2NH
N
2-(-)-
. , .
, ,
.
. 1. - , .
2. .
3. , . . ,
233

-.
.
.
. .
. , , , , , .

.
(Sulfapyridazinum)
Sulfamethoxypyridazine*
H2N
SO2NH
NN
OCH3
6-(-)-3-
.
- (Sulfapyridazinum-natrium)
H2N
SO2N
NN
OCH34H2O
Na
6-(-)-3-
(Phthazinum)
O
CHN
SO NH
NN
OCH!
COH
O
6-(-)-3-
. , , .
234
(Slazopyridazinum)
Salazodine*
OH
O
C
HO
N=N
SO2NH
NN
OCH3
5-(-[N-(3--6)-])-
. .

.
(Salazodimethoxinum)
OH
O
C
OCH3
HO
N=N
SO2NH
N
OCH3
5-{-[(2,4--6)-]-}
. .
.
(Bactrim)
Co-Trimoxazole*
, :
.
235
H2N
SO2NH
CH3
3-(-)-5-
H2N
N
N
OCH3
CH2
NH2
OCH3
OCH3
2,4--5-(3,4,5-)-
.
, - ,
.

(Sulfatonum), .
,
, , ,
.
, .
(I) 5- .
4
5
O1
I.
O2N
O
II.
(II),
5- (III) (IV):
O2N
O
III.
O2N
O
IV.
CH0NR
, ,
. ,
.
237
(Furacilinum)
Nitrofural*
O2N
CH0NNHCNH2
5-
. - , , . (1 : 4200, NaCl
), (1 : 590), , .
.
5- ,
,
, . :
CH 3COONO 2
C
H
OCCH3
( HNO 3 C 5H5N)
OCCH3
0
(CH3 CO)2 O
(
)
&'
O2N
C
H
OCOCH3
OCOCH3
H2 O
. H 2SO 4
5-
&'
O2N
5-
&'
O
H
O2N
H 2N NH CO NH 2
CH0NNHCONH2
238
,
,
.
. 1.
- , .
, , .

, . ,
:
CH0NNHCNH2
NaO
&'
NaO
OH O
O
+
&'
NaOH
O2N
CHN0NCNH2
H2 O; t
NaOH
O
H + H2NNH2 + Na2CO3 + NH36
2. : 230236 ( ).

5-, . :
95 %- ,
10 %- CuSO4,
10 %- NaOH
, 30 %-
NaOH
95 %- e, 5 %-

239
. . .
,
:
O
H2NNHCNH2
-
t
N26 + Cu2O5 + NH36 + Na2CO3
(I) ( , ).
. 1. , , , = 1/4 . .

.

. - , :
O2N
&' O2N
CH0NNHCONH2
O
H
+ 2I2 + 6NaOH 89
+ N26 + 4NaI + Na2CO3 + NH36 + 3H2O

:
, , :
NaI + NaOI + H2SO4 89 I2 + Na2SO4 + H2O
I2 + 2Na2S2O3 89 2NaI + Na2S4O6
.
2. , .
3. 50 %- .
. ,
.
. ,
.
- .
240
(Furadoninum)
Nitrofurantoinum *
O
CH0N
NH H2O
O2N
O
N-(5--2-)-1-
. -
, .
95 %- , .
. 1. - .
2. , ,
- .
. 1. .
2. ,
, , = . .
3. -.
. ,
.
. .
(Furasolidonum)
Furazolidone *
CH0N
O2N
O
N-(5--2-)-3--2
. - , . ,
95 %- .
. 1. .
2. ,
, ,
.
241
. 1. KOH.
2. -.
. , .
. .
(Furosemidum)
Cl
SO2NH2
O
CH2NH
COOH
4--N-(2-)-5-
. () .

, ,
2-:
2-
(Pyracetamum)
O
0
CH2CNH2
O
2-
. ,
, .
. 1.
- 1 %- 230350 .
242
2. .
. (.
).
. , .
. () .
()
(Polivinylpyrrolidonum)
CCH2
H
N-
, , , .
. , .
, , , , ,
.
. - :
NH 3
H 2O
HC
CH
CCH2
H
. 1. 0,1 .
2. , ( ).
3. .
. , , . -243

.
2. (, ).

, ,
.
. 15 %- 0 +20 , 10 +30 .
. 35 %-
3000040000 .

, , . :
(Enterodesum), . . 126002700 ()
; (Haemodesum) -
, 6 % (. . 126002700) Na+, K+,
Ca2+, Mg2+, Cl, HCO3; (Neohaemodesum), (80002000),
.
,
:
N NH
N NH
H
-5
O
N NH
N NH
-5 ,
.
244
(Antipyrinum)
Phenazone*
CH3
NCH3
1--2,3--5
. , . ,
, , .
. 1883 . :
3540 C; H 2O
O0C
100 C
C 2H 5OH
OC2H5 H
OC2H5
CH3
N
CH3
N
&'
C6H5SO3CH3
CH3
NH
SO3
NNC6H5
H2C CCH3
O0C
H2 CCCH3
NaOH
1--3--5
SO3Na
89
CH3
NCH3
+
+ H2O
. 1. - :
245
ON
H+
C6H5
CH3
N
CH3
N
NaNO2
CH3
NCH3
C6H5
2. (III)
:
CH3
NCH3 2FeCl3
C6H5
3. (110113 ).
4. .
, - - :
N 0 N
O
CH3COOH
C6H5
CH3
N
CH3
N
CH3
N
CH3
N
ON
NH2
C6H5
.
5.
( ).
6. 2- (1:20000):
O
NO2
,
.
.
,
.
246
. , , , = 1/2 . .
, .
:
C6H5
CH3
NCH3
+ HI
CH3
I
NCH3 + I2 79
N
O
C6H5
I2 + 2Na2S2O3 89 2NaI + Na2S4O6

,
,
:
CH3COONa + HI 89 CH3COOH + NaI
, , ,
.
. , .
. , . (1020 %- ) (, ).
(Analginum)
Metamizole Sodium *
NaO3SH2C
N
O
CH3
N
CH3
N
H3C
H2O
1--2,3--4--5-N- ,
.
,
. .
247
. 1,5 , 160
95 %- , ,
.
. :
CH3
NCH3
H 2C
H3C
OH
SO3Na
NaO3SH2C
CH3
NCH3
H3C
C6H5
C6H5
. 1.

( ), :
5SO2 + 2KIO3 89 I2 + 4SO3 + K2SO4
(FeCl3, , HNO3 .)
.
2. SO2 ( ):
H O; HCl
CH3
N`CH3
C6H5
N`
O
CH3
N
`
CH3 Cl +
N
N`
NaO3SH2C
H3C
H3C
C6H5
+ SO26 + CH2O6 + NaCl

3. Na+ ( ).
. 4-.
():
CH3
NCH3
C 6H 5OH; K 3[Fe(CN) 6]
NH4OH
O0
0N
O
C6H5
CH3
N
CH3
N
H2N
C6H5
- (),
.
248
. , , = 1/2 . . , 30 :
NaO3SH2C
N
O
CH3
NCH3 + I + 2H O 89
N
2
2
H3C
C6H5
N
O
CH3
I + NaHSO4 + HI + CH2O
N
CH3
N
89
H3C
C6H5
. , .
. . , . ,
.
(Butadionum)
Phenylbutazone *
NN
H9C4
1,2--4--3,5
. , . , ,
, ,
, . 249
, - :
H9C4
NC6H5
OH
NC6H5
NaOH
C6H5
C6H5
&'
H9C4
N
ONa
NC6H5
H9C4
C6H5
. - :
H9C4CH
C
O
OC2H5
OC2H5
HNC6H5
C 2H5 ONa
HNC6H5
H9C4
O
O
N NC6H5
ONa
N NC6H5
89 H9C4
C6H5
C6H5
. 1. , . .
:
NHNH
[O]
N 0 N
2. . 250
, -:
C6H5
H9C4
89
O
NC6H5
Cu2+5 + Na2SO4
ONa
NC6H5 + CuSO4 89
H9C4
C6H5
3. (104107 ).
. .
FeCl3 . - .
. , , , = . .
. , .
. , .

, 1, 3:
4 3
5 12
N
H
, , , .
(Mercazolylum)
Tiamazolum *
N
SH
CH3
1--2-
251
.
, .
, , , .
. 1. : ;
-; .
2. , ,
.
3. - .
. , , , = . .
, ,
:
N
N
SH
+ AgNO3 89
CH3
N
N
SAg
+ HNO3
CH3
HNO3 + NaOH &' NaNO3 + H2O

. , ,
.
. .
(Metronidazolum)
Flagyl *
N
N
O2N
CH3
CH2CH2OH
1-(-)-2--5-
. -
. , .
. 1. -
0,001 %- 312 ; 1%
- 1 = 515548.
252
2. 4 %- - ,
, .
3. 148153 .
4. :
N
CH3
H2N
CH2CH2OH
O2N
[H]
NaNO2
HC l
CH3
CH2CH2OH
OH
N
N
89
CH3
Cl
NaOH
CH2CH2OH
89
N
N
N0N
ONa
CH3
CH2CH2OH
. 1. ,
, = . .
2. -.
3. .
. ,
.
. .
. .

,
:
253
, , .
(Clophelinum)
Catapresan *,Clonidini hydrochloridum
N
N
Cl
NH
HCl
Cl
H
2-(2', 6'-)-
. , ,
, .
. 1. - 0,02 %- : 2722 2802 .
2. Cl.
. ( ) () , , = . .
. ,
.
. .

.

(Diaethylamidum acidi nicotinici)
Nicethamidum*
O
N(C2H5)2
N
.
. , 95 %-
, - .
254
.
:
COOH
N
HN(C 2H5) 2
O
N(C2H5)2
Cl
N
. 1. , :
O
N(C2H5)2
COONa
NaOH; t
+ HN(C2H5)26
2. , - :
C
4
O
N(C2H5)2
CuSO4
89
O
N(C2H5)2 Cu SO4
89
2NH4 SCN
O
N(C2H5)2 Cu (SCN)25 + (NH4)2SO4
3. .
2,4- , ,
-:
255
R
N
NO2
NaOH
NaCl
NO2 Cl
NO2
&'
R
+
Cl
NO2
&'
HNCH0CCH=CH
O
N2
C
NO2 OH &'
H &'
N2
NO2
R
+ HC=CCH=CH C
&'
HO
N2
NH2
N2
O
H
4.
:
Br2 + NH4SCN 89 BrSCN + NH4Br

()
R
N
+ BrSCN 89
R
+
2H O
Br 89
SCN
HC
89
O
CH
C
C
R
OH + NH SCN + HBr
2
H
.
256

, , :
CCH=CHC=C
OH
H
+ 2H2N
2H O
R
89 R
N=CHCH=CHC=CHNH
, .
. . , ,
, (2 : 1), = . .:
CON(C2H5)2
N
COONa
1. H 2SO 4
2. NaOH
+ HN(C2H5)26
N
+
HN(C2H5)2 + H3BO3 89 [H2N(C2H5)2]BO2 + H2O

+
2NH(C2H5)2 + 4H3BO3 89 [H2N(C2H5)2]2B4O72 + 5H2O
[H2N(C2H5)2]BO2 + HCl + H2O 89 [H2N(C2H5)2]Cl + H3BO3

+
[H2N(C2H5)2]2B4O72 + 2HCl + 5H2O 89 2[H2N(C2H5)2]Cl +

+ 4H3BO3
.
. . .
. .
(Cordiaminum)
25 %- .
. . .
. .
. .
. , .
257
(Nicodinum)
NHCH2OH
N

. . , 95 %- ,
.
. :
O
HC
NH2
O
NHCH2OH
. 1. , :
CONHCH2OH
H 2O
COONa
NaOH; t
+ NH36 + CH2O6
2.
2,4- (. ).
- .
3.
- ( . . ).
. , , , = 1/2 . .:
O
NHCH2OH + 4NaOH + I2 89
COONa
89
+ 2NaI + NH36 + HCOONa + 2H2O

258
.
.
. ,
, 20 .
. , ,
.
(Isoniazidum)
CONHNH2
N
()
. ,
. , ,
, .
. :
CH3
[O]
N
-
COOCH3
COOH
CONHNH2
NH2NH2
CH3OH
. 1. ;
-, - ,
:
CONHNH2 C
NNH2
NNH2
OH
CuSO 4
H2NN
OCuO
C
t
H2 O
N
COOH
89
259
+ N26 + Cu2O5
2.
,
:
CONHNH2
COOH
+ 4[Ag(NH3)2]NO3 + H2O
+ 4Ag5 +
+ 4NH36 + 4NH4NO3 + N26

3. 2,4- - , -.
. , , , = 1/4 . .:
CONHNH2
COONa
+ 2I2 + 5NaHCO3 89
+ N26 + 4NaI + 5CO26+ 4H2O
N
I2 + 2Na2S2O3 89 2NaI + Na2S4O6
.
. , .
. .
(Phthivazidum)
CH
CONHN
N
OH
OCH3
H2O
3--4- ,
. -
, . , 95 %- , .
.
:
260
CONHN
OH
H2O
OCH3
CH
CONHNH2
N
OH
OCH3
. 1. 2,4- - ,
.
2. - -.

, - (
):
CH
CONHN
CH
CONHN
NaOH
N
OH
OCH3
H Cl
ONa
OCH3
HC l
CH
CONHN
Cl
N
OH
OCH3
3. :
COOH
H2O; t
2HCl
N
OH
OCH3
CH
CONHN
O
H
OH
. .
261
+ NH2NH22HCl
OCH3
,
, , .
:
CONHNH2
O
C
+
NaNO2
N=N=N
HC l

.
:
O
H
NaOH
OH
OCH3
OCH3
ONa
. ,
. - -,
- , = . .:
HClO4
N
OH
CH
CONHN
CH
CONHN
OCH3
OH
OCH3
ClO4
(
). .
. .
. .

:
"
#
!
$
H
262
, , .
(Promedolum)
Trimeperidini hydrohloridum*
H5C6
H3C
OCC2H5
HCl
O
CH3
N
CH3
1,2,5--4--4-
.
. , , .
. 1. Cl.
2. .
3. (
) .
4. .
. 1.
() ,
, = . .
2. , = . .
3. , , = 1/6 . .
4. , = . .
5. -.
. .
. ().

1,4--(1--[2,2,2]-):
4
5
6
8
7
, , , , .
263
(Aceclidinum)
Aceclidine*
OCCH3
N
COOH
OH
3-
. .
, , .
. 1. ,
-
, -.
2. . - :
OCCH3
N
+ NH2OH HCl
2. H C l
+ CH3C
3 CH3`+
O
NHOH
OH
1. NaOH
+ FeCl3 89 CH3C
+ NaCl + H2O
NHOH
O
NHO
Fe3+ + 3HCl
3. - (
(III) ).
. 1. ,
, = . .
2. , = . .
3. ( ).
. , .
. () .
(Oxylidinum)
Benzoclidini hydrochloridum*
OCC6H5
HCl
O
N
3-
264
. . , ,
.
. 1.
(190195 ).
2. -
( ).
3. Cl.
4. (246250 ).
. 1.
() , = . .
2. .
. , .
. , .
(Phencarolum)
Quifenadine*
C6H5
C6H5
OH HCl
N
-3-
. ,
. , .
. 1. Cl.
2.
, :
C
N
C6H5
C6H5
OH HCl + NH4[Cr(NH3)2(SCN)4] 89
C
89
C6H5
C6H5
OH [Cr(NH ) (SCN) ] + NH Cl
3 2
4
4
H
3. -
( ).
. 1.
() , = . .
265
2. -.
. , .
. .

, , .
.
H
O
H
O
N
R
N! "
O
#
O
R1
$
N
N
O
R2
O
H
( )

.
:
1) -,
:
H
O
12 O
N
H
OH
N
O
2) -,
:
H
O
12 HO
266
56 . 5- (, 5- ), 5,5- (,
5,5- ) ,
. , , , :
H
O
O
N
R
N
R
+ NaOH 12 NaO
+ H2O
O
R1
R1
N
N
Barbitalum
Barbital*
O
N
C 2H 5
C 2H 5
N
O
5,5-
H
Phenobarbitalum
Luminal*
O
N
C 2H5
C 6H5
N
O
5--5-
H
Benzonalum
Benzobarbitalum*
Benzobarbital*
O
O
O
C 2H 5
C 6H 5
O
CC6H5
1--5--5-
-
Aethaminalum-natrium
Nembutal*
Pentobarbitalum Natrium*
O
NaO
H
C 2H5
CH CH2 CH 2 CH3
O
CH3
5--5-(2'-)-
267
2
O
Hexenalum
Hexobarbital Sodium*
Hexobarbitalum Natrium*
NaO
CH 3
N
CH3
1,5--5-(-1'-)-
-
Thiopentalum-natrium
Thiopentalum Natricum cum
Natrii Carbonate*
Thiopental Sodium
with Sodium Carbonate*
O
C 2H 5
NaS
CH CH2 CH2 CH3 + Na2CO 3
N
O
CH3
5--5-(2'-)-2-

. ,
()
(-), . - , , . - ,
, .
.
:
1) ;
2)
.
:
H2C
COOC2H5
C2 H5 Br
C 2H5 ONa
COOC2H5
H5C2
H5C2
H5C2
H5C2
COOC2H5
COOC2H5
COOC2H5
COOC2H5
H2N
C=O
H2N
C 2H5 ONa
O
89 NaO
C2H5
C2H5
5,5-
268
H Cl
O
H
C2H5
C2H5
O
5,5-
. 1. :
AgNO3 ;
Co(NO3)2 CaCl2 - ;
CuSO4 ( ):
-
;
- ,
;
- ;
- ;
, -, ;
- - .
(
).
.
, :
O
N
R1
O
OCuO
R1
N
=O
N
R1
Cu
2.
,
:
H
O
R1
+ 5NaOH 89
R
R1
CHCOONa + 2NH36 + 2Na2CO3
CO2 :
Na2CO3 + 2HCl 89 H2O + CO26 + 2NaCl
269
R
R1
CHCOONa + HCl 89
R
R1
CHCOOH + NaCl
3. :
)
:
, ;
- ;
) - :
- - ;
.
1 5.
4. ( ):
H
O
H
C2H5
. H 2SO 4
N
H
NaNO 3
C2H5
N
H
NO2
5. ( FeCl3 - ):
6C6H5COONa + 2FeCl3 + 10H2O 89 (C6H5COO)3FeFe(OH)37H2O5 +
+ 3C6H5COOH + 6NaCl
6. KMnO4 ( ):
O
NaO
N
N
CH3
+ Br2 89 NaO
CH3 O
CH3
N
CH3 O
Br
Br
7. - :
) :
270
O
NaS
C2H5
CH(CH2)2 CH3 + 6NaOH + (CH3COO)2Pb 89
CH3
H5C2
CHCOONa
89 PbS5 + HC(CH2)2CH3 + 2NH36 + 2Na2CO3 + 2CH3COONa
CH3
:
5PbS + 2HCl 89 H2S6 + PbCl2
) -
.
8. :
) Na+;
)
HCl:
O
NaO
R1
R2
+ HCl 89 O
R1
R2
+ NaCl
. , ,
5-- 5- .
, ,
-
( ) .
:
) ( HCl; );
) ( ).
. 1. - :
)
.
() , 271
( ) NaOH
, , = . .:
H
O
R1
R2
+ HC
CH3 89 O
CH3
R1
R2
R2
O
+
N
H
CH3
CH3
O
R
+ HC
R1
+ CH3ONa 89 NaO
CH3O + HC
N
H
N
R2
+ CH3O
R1
CH3 89 CH3OH + HC
CH3
CH3
CH3
) -
.

, = . .:
H
O
R1
R2
+ NaOH 89 NaO
R1
R2
+ H2O
) , , = . .:
O
NaO
R1
R2
+ HCl 89 O
R1
R2
272
N
O
+ NaCl
.
(%)
:
X=
VHCl K T 100 100

% K,
m (100 % )
% ;
,
.. . . NaOH.
-
.
2. . . ,
. -.
3. . (
) 5 %-
( ), = . .:
H
O
R1
ONa
R
R1
ONa
R
Na 2CO 3
R1
+ O
OAg
R
N
H
R1
89 2O
AgNO3
OAg
R
N
O
R1
89
R1
N
N
OAg
R
R1
ONa
Ag
Na
+ AgNO3
Na2CO 3
2AgNO 3
2O
N
N
OAg
R
R1
OAg
. . .
- 0,51,0 ,
273
, , , ,
.
0,050,25 % , - 56 % .
, ex tempore.
. .
. -
.

.
(Hexamidinum)
Primidone*
C2H5
C6H5
N
O
H
5--5--4,6
. . , .
. 1. , :
C2H5
C6H5
NaOH; t
2NH36 + Na2CO3 + HCH +
H5C2
+
274
H5C6
CHCOONa
2.

(- ):
SO3H HO3S
HO
CH
HO
OH
SO3H HO3S
. , = 1/2 . .:
. .
. .

-2,4-
:
OH
NH
O
H
OH
, , .
(Methyluracilum)
O
NH
H3C
O
H
6-, 2,4--6-1,2,3,4-
275
(Kalii orotas)
O
NH
KOOC
H
-4-
(Phthorafurum)
Tegafur *
O
F
NH
O
O
N !-(2-)-5-
. .
,
, , .
. 1.
: ;
.
2.
();
30 %-
(); -
- ().
3. -
270 (), 275
(), 285 ( ).
4. :
) .
pH = 4,05,0
:
2F + CaCl2 89 CaF25 + 2Cl
276
) . -, , -
:
Fe(SCN)3 + 6F 89 [FeF6]3 + 3SCN
5. - (III)
- .
6. .
. :
1) (. ),
= . .:
ONa
OH
N
H3C
+ NaOH 89
H3C
+ H2O
H
H
2) , = 1/2 . .
: 1) ( 600 ), , = . .:
K2CO3 + 2HCl 89 2KCl + H2O + CO26
2) (III) ;
3) -.
: 1) , , , = 1/2 . .
O
F
NH
O
F
+ Br2 89
NH
+ HBr
Br
O
2KI + Br2 89 I2 + 2KBr

I2 + 2Na2S2O3 89 2NaI + Na2S4O6
2) -.
277
. , , .
. ;
; - .

1,4- 1,2-, , - :
O
5
6
7
8
7
8
O
1
3
2
K
.
(Neodicumarinum)
Ethyl biscoumacetate*
OC2H5
OH C=O OH
CH
O
O O
-(4--3)-
. ,
. ,
, , .
.
4- , :
278
COOH
C 2H 5OH
COOH
COOC2H5
O
C
H
[H]
COOC2H5
OH
COOC2H5
OH
COOC2H5
O
+ C
+
H
O
O
89
4-
OC2H5
OH C=O OH
CH
89
O O
. 1. () - .
2. , .
-(4--3)- :
OH
COOH OH
CH
.
:
- ; .
3. -, () - .
. -(4--3)- ,
.
. , , = . .:
279
OC2H5
OC2H5
OH C=O OH
ONa C=O OH
CH
CH
NaOH
H 2 O
O
O
O
O O
O O
.
. ,
.
. ; .
, .

.
(Dibazolum)
Bendazol*
N
N
CH2
HCl
H
2-
. , , - . .
, ,
, .
. -
:
NH2
NH2
o-
+ C
CH2
N
2H2O
OH
CH2
HCl
89
N
N
H
CH2
280
HCl
. 1.
:
N
N
HCl + NH4OH 89
CH
N
N
89
|
5 + NH4Cl + H2O
CH2
2.
- (
25 ):
N
N
I2; H
CH2
CH2
I2HI5
. -
(III) .
. ,
() , , = . .:
2
N
N
HCl + 2HClO4 + (CH3COO)2Hg
CH2
CH 3COOH
89 2
N
N
CH2
HClO4 + 2CH3COOH + HgCl2
.
. , .
. . ( , , 281
, )
0,02 (12 % ). ; .

([b]) ,
:
4
3
5
6
N1
H
, ,
.
(Indometacin*)
O
H3CO
6
7
O=C
CH2COH
CH3
Cl
1-(-)-5--2--3-
. - .
, ,
.
.
.
. . .
, , .
(,
, ).
0,025
0,05 .
282
, :
5
4
3
6
7
N
1
: 8- , , ; 4-
, ;
8- , .
(Nitroxolinum)
Nitroxoline*
NO2
N
OH
5--8-
. - , . .
. ,
-, -.
. 8- 8-, ,
:
H
HNO3
OH
O = C CH =CH 2
[H]
NO2
OH
NH2
OH
283
NO2
89
NaNO 2; H Cl
N
OH
OH H
8-
8--1,2-
NO
NO2
[O]
89
OH
OH
5--8-
. 1. (III)
- .
2. - 0,001 %-
220460 : 242, 356
455 .
3.
- :
NO2
N3N
NH2
OH
NaNO2
[H]
OH
Cl
H Cl
NaOH
N
OH
OH
N=N
89
NaO
N
ONa
4. - :
ON=O
+ NaOH 89
N
O
OH
284
ONONa
+ H 2O
. 5,7--8- 5--8 .
. 1. ,
. 0,1 - ,
, = . .:
NO2
NO2
+ CH3ONa
+ CH3OH
N
ONa
OH
.
2. , .

0,1 , , = . .:
NO2
NO2
+ HClO4
HCOOH
+
ClO4
OH H
OH
.
3. .
. , .
. (, .) 0,05 .
(Chingaminum)
Chloroquine diphosphate*
CH3
C2H5
HNCHCH2CH2CH2NC2H5
Cl
2H3PO4
4-(1 !--4 !-)-7-

285
. , , .
. , 95 %- , , .
. 1. - 0,001 %-
0,01 220 350
: 257, 329, 343 .
2. , 204,5207 .
3. :
) H3PO4 + 3AgNO3 89 Ag3 PO45 + 3HNO3
) H3PO4 + 3NH4OH + MgSO4
NH 4Cl
MgNH4PO4 5 + (NH4)2SO4 +
+ 3H2O
) H3PO4 + 21HNO3 + 12(NH4)2MoO4 89

89 (NH4)3PO4 12MoO3 5 + 21NH4NO3 + 12H2O
. , , , = 1/2 . .:
C2 H 5
CH3
HN `CH `CH2)3 `N`C2H5
Cl
2H3PO4 + 2HClO4 89
CH3
C2H5
+
HNCH(CH2)3NC2H5
89
H
Cl
(ClO
4 )2 + 2H3PO4
H
.
. , .
286
. ; .
(Chinocidum)
Quinocide*
H3CO
2HCl
N
NH(CH2)3CHNH2
CH3
6--8-(4 !-)-
. - ,
. , 95 %-
, , .
. 1. - ,
( ).
2. .
. 1. , ,
= 1/2 . .
-
, . . .
2. ,
() , , = 1/2 . .
. .
. ( -
).
, .
3- .
287
(Ofloxacinum*)
(Tarivid), (Zanocin)
COH
F
N
H3CN
CH3
9--2,3--3--10-(4--1-)-7-7H--[1,2,3-de]-1,4-
(Norfloxacin*)
COH
F
HN
N
C2H5
1--6--1,4--7-(1-)-4--3-
(Ciprofloxacine*)
(Ciprobay), (Cifran)
COH
F
HN
N
CH
H2C
CH2
1--6--1,4--4--7-(1-)3-
288
(Lomefloxacin*)
(Maxaquin)
O
H3C
HN
COH
N
F
C2H5
1--6,8--1,4--7-(3--1-)-4-3-
, , , ,
. .

, -.
38 .

, .
.
0,2 0,4 , 0,2 %-
50 100 (100 200 ) 1 %-
(, ).
. , , , - , , .

.
(Aethacridini lactas)
NH2
H2N
OC2H5
OH O
CH3CHCOH
2--6,9-
289
. ,
. , , .
. . -2- :
CH3
CH3
Cl2
Fe
O2N
O2N
Cl
2--4-
COOH
89
Cl
[O]
O2N
2--4-
OC 2H 5
COOH
H 2N
-
O2N
OC2H5
NH
5--4 ! --2-
, , 9-, .
, :
COOH
OC2H5
POCl3
O2N
NH
Cl
89
OC2H5
NH3
OH
O2N
2--6--9-
NH2
89
OC2H5
[H]
O2N
2--6--9-
NH2
89
OC2H5
OH
CH3 CH C OH
H2N
290
NH2
89
CH3CHCOH
H2N
OH
OC2H5
. 1.
, .
2.
, :
NH2
NH2
OC2H5
89
H2N
OH
CH3CHCOH + NaOH 89
H2N
OH
OC2H5
OH
+ CH3CHCONa + H2O
OH
2CH3CHCONa + H2SO4 89 2CH3CHC OH + Na2SO4
OH
5CH3CHCOOH + 2KMnO4 + 3H2SO4 89 5CH3CH +

+ 5CO26 + 2MnSO4 + K2SO4 + 8H2O
3. - :
NH2
H2N
CH3CHCOH
N
NH2
89
OH
OC2H5
N3N
OC2H5
N
291
NaNO2
H Cl
OH
Cl + CH3CHCOH
4. 0,1 -
, 95 %- .
. 1. , , , = 1/4 . .:
NH2
NH2
89
OH
OC2H5
+ CH3CHCOH + 2HCl
H2N
CH3CHCOH + 2ICl 89
H2N
OH
OC2H5
I
I2 + 2Na2S2O3 89 2NaI + Na2S4O6
.
2. ,
.
. .
. .

, .
5
6
3
2
7
8
10
, , :
S
R!
R
292
HCl
10 . , , 10 (, , , )
, 10- (, ) - .

S
R!
R

Aminazinum
Chlorpromazine
hydrochloride*
CH 3
CH2 CH 2 CH2 N CH 3 H Cl
2--10-(3'-)
Diprazinum
Promethazine
hydrochloride*
Propazinum
Promazine
hydrochloride*
Aethaperazinum
Perphenazine
hydrochloride*
Triphthazinum
Trifluoperazine
hydrochloride*
Aetmozinum
Moracizin
hydrochlorid*
R!
Cl
CH 3 CH 3
CH2 CH N CH 3H Cl
10-(2'-)
CH3
CH2 CH2 CH2 N CH 3 H Cl
10-(3'-)
(CH2 )3
(CH 2)2 OH2HCl
2--10-[3'-(1''---4 '')-]-
(CH2)3
Cl
CH32HCl
2--10-[3'-(1'' --4 '')-]-
O
C (CH2 )2
CF3
O
N
OHCl
2--10-(3'-)-
293
NH C OC2 H5
.
. ,
, .
. 1. . H2SO4, , HNO3, FeCl3 .,
. . , -, -, .
: , 9-S-
9,9-S-:
O
S
S
R!
[O]
R!
O
R!
[O]

, :
- ;
- ;
- ;
-, - .
,
:
+
(BrBr2)
H2SO4 :
;
- ;
- .
2.
.
3.
. , .
4. ( )
.
294
5. - -.
.
: , 2-, .
. 1. .
() .
: ; , .
2. .
3. ( ).
4. , E = 1/2 M. .
5. , .
6. .
7. .
.
, , , , .

, ,
, , (, , ).
, ! ,
( ).
. .
; .
, 10 (), .

, 1,4-:
H
9
8
2
3
7
6
N4
() .
295
(Chlozepidum)
Chlordiazepoxide*
Elenium, Librium
NHCH3
N
N
Cl
7--2--5--3-1,4--4-
(Sibazonum)
Diazepam*
Seduxen, Valium
CH3
N
Cl
7--1--5--2,3--1-1,4--2-
(Nozepamum)
Oxazepae*
Tazepam
N
N
Cl
OH
7--3--5--2,3--1-1,4--2-
296
(Nitrazepamum)
Nitrazepam*
Radedorm, Eunoctin
N
N
O2N
7--5--2,3--1-1,4--2-
(Phenazepamum)
Fenazepam
N
N
Br
Cl
7--2,3--5-(-)-1-1,4--2-
. . - . , .
.
1,4- 4. NHCO ,
, .
. 1. (H2SO4, HCl,
HlO4) , -.
2.
.
3. .
297
4. :
N
N
Cl
NH2
OH
HCl; t
C=O
Cl
NaNO2
HC l
NaO
+
N3N
89 Cl
N=N
OH
C=O Cl
C=O
Cl
NaOH
5. - .
6. ( , ,
).
7. H3PO4 ,
:
NHSO2H
HO2SO
NH2
+ 3HC
O
H
89
NHSO2H
O
NHSOCH
89
OH
OH
=NH
NHSOCH
O
298
+ HCOH
H OSO2H
. ,
, = . .

.
. , , .
. (, ). , ,
.
, .
.

,
:
1
N
2
N
3
N7
N9
H
(Acidum adenosintriphosphoricum)
, Fosfobion
NH2
N
N
N
OH
N
O
OH
OH
CH2OPOPOPOH
O
HO OH
-5 !- ,
9--D-

, .
.
299
. . 1 %- (Solutio Natrii adenosintriphosphatis 1 % pro

injectionibus) pH = 7,07,3.
. 1. ,
FeCl3 HCl .
20 .
2. - :
PO43-+ Mg2+ + NH4+
NH 4OH
NH 4Cl
MgNH4PO4 5
3. .
.
.
, .
. , ,
.
. , ,
1 %- .
(Riboxinum)
OH
N
N
N
CH2OH
HO OH
9--D-
. , , . 300
, ,
.
. 1. - .
2. , .
3. : 47 54 (1 %- ).
. .
. , .
. , , , , , . .

, ,
, .

.
,
, , . , (,
, ).
.
-
:
, , .
, ,
. ,
. , , , ,
.
:
1. .
2. .
, . :
1. .
2. - .
3. .
4. .
5. ().
6. .
302

, .
.

,
, , .
, , , .
:
1. , , (
).
2. ( ).
3. ( ).
4. ( ).
5. -
H3PO412MoO32H2O .
, (
).
6. -
H3PO412WoO32H2O.
7. -
SiO212WoO34H2O.
8. 5 %- .
9. .
, 12 ,
45 .
,
.
, :
; ;
; .
:
1. .
2. .
3. ( ).
4. (
).
303
5. (
).
6. ( - ).
;
.
:
1. , .
2. - :
) , ;
) ;
) ( ,
, );
) .
3. .
4. , .
5. - .
,
, .
,
.
:
1. (I) (II) (, ):
1
9
8
7
N
5
I.
N
5
2
3
II.
2. (, , , ):
7
NCH3
6
3
4
304
3. (III) () (IV)
( ):
5
6
7
8
4
3
III.
N2
IV.
4. ():
5
HN
1
N
3
5. (, , ):
4
N1
H
6. (, , ):
6
1
2
3
N
N
NH
8
N
9
7. 1- ():
CH3
7
6
1
5
N
4
2
3
8. (, ).

, , , ,
Fabaceae, Euphorbiaceae, Nymphaeaceae, Lycopodiaceae.
.
305
(Cytisinum)
NH
N
O
1,2,3,4--6, . .
. . , , .
. 1.
.
2. Co(NO3)2 - .
3. FeCl3 ,
.
4. 154157 .
5. : 120 123 (2%- ).
. , , , = . .:
NH + HCl 89
H
+
NH Cl
. .
. .
0,15 %- .
(Pachycarpini hydroiodidum)
N
HI
CH2
N
-
.
. .
, ,
.
306
. 1. I.
2. , :
) ( );
)
.
3. - ,
.
4. : +8,6 +9,6 (7 %-
).
. 1.
(II) ,
, = 1/2. .:
2
CH2
HI + Hg(CH3COO)2 + 4HClO4 89
H
+
89 2
CH2
(ClO4 )2 + HgI2 + 2CH3COOH
H
2. , , ,
= . .
3. ,
= . .
4. .
. .
. ; , .

,
. .
: (I) -2- (II).
307
COOH
NCH3
OH
NCH3
I.
OH
II.

(, , .).
, .
(Atropini sulfas)
CH2OH
NCH3
OCCHC6H5
O
H2SO4H2O
2
(+),()- ,
1833 . ,
. 114116 ,
,
:
O
NCH3
CH2
OCC
.
. ,
.
. 1. .
HNO3
, 0,5M
KOH , :
308
CH2OH
NCH3
OCCHC6H5
O
H2SO4
2H O; t
HNO!
HOOCCHCH2OH
89
NCH3
OH H2SO4 + 2
2
HOOCCHCH2OH
HOOCCHCH2OH
O2N
NO2
3HNO!.; t
3H O
2KOH
C H#OH
ON=O
KOOCCCH2OH
O2N
NO2
89
ONOK
2. SO42.
3. (115
117 ) .
4. .
5. ( ) H2SO4
K2Cr2O7:
HOOCCHCH2OH
K2Cr2O7; t
H 2SO 4
.
,
.
309
. 1. ,
, = . .:
CH2OH
+
NCH3
OCCHC6H5
SO42 + HClO4 89
2
CH2OH
+
89
NCH3
OCCHC6H5
ClO4 +
CH2OH
+
NCH3
OCCHC6H5
HSO4
2. - , = 1/2. .
3. .
. .
. (, )
.
(Scopolamini hydrobromidum)
Hyoscini hydrobromidum*
CH2OH
O
NCH3
OCCHC6H5 HBr3H2O
O
()- ,
. . , ,
.
. 1. Br.
2. ( ).
310
3. (192196 ) : 22 26 (5 %- ).
. , 0,1 KMnO4
5 . .
. 1.
(II) ,
, = . .
2. , , = . .
. ,
.
. .

, .
.
:
O
NCH3
OH
R1
C CH
R2
Cl
NCH3
R1
OCCH
R2
(Homatropini hydrobromidum)
Homatropine hydrobromide*
OH
NCH3
OCCHC6H5 HBr
O

311
. . , ,
, .
. 1. Br.
2. .
3. KOH , .
4.
, - ( ,
).
. 1.
(II) , = . .
2. -
, = . .
. , .
. () . .
(Tropacinum)
Diphenyltropin hydrochloride*
C6H5
NCH3
OCCH
HCl
C6H5
O

. . , , .
. .
. 1. :
O
NCH3
OCCH
HCl
H O; t
HNO !
COOH
89
NCH3
OH HCl +
C
H
312
HNO3 .; t

O2N
89 O2N
COOH
NO2
NO2
C
O2N
2KOH
2H O
NO2
O
89
O2N
COOK
NO2
NO2
OK O N
2
NO2
2. Cl.
3. (212216 C).
.
(II) , = . .

, = . .
. , .
. , .

, , . , - -,
, .
, .
(Cocaini hydrochloridum)
COOCH3
NCH3
OCC6H5 HCl
O

. , , 313
. ,
, , .
. 1. Cl.
2. KMnO4 ( ).
3. H2SO4
, , ,
, , ,
, :
COOCH3
NCH3
OCC6H5 HCl
. H SO"
HO
O
COOH
+
89
NCH3
HSO4 + C6H5COOH + CH3OH
H
C6H5COOH + CH3OH
. H SO "
C6H5COCH3 + H2O
O

.
4. ( 195 C); : 71 73 (2,5 %- ).
. 1.
(II) , = . .
2. , = . .
3. , = 1/2. .
. , .
. .

, 1-, 1935 . .
. . .
314
(Platyphyllini hydrotartrs)
CH3 CH3
CH3CH=CCH2CHCOH
HOCHCOOH
C=O
C=O HOOCCHOH
O
N
CH2
.
, .
, ,
.
. 1. - (
).
2. .
3. - H2SO4 .
4.
( ).
5. : 38 40 (5 %- ).
.
5 %- .
. 1. ,
, = . .
2. - , = . .
3.
000-II.
. .
. (, )
.

, :
315
H3CO
6'
7'
5'
8'
CH2
4'
3'
4
8
7
CH=CH2
OH
3H2O
2'
1'
6'--(4')-[5--(2)]-
, :
1) ( );
2) ( ).

, .
: , , .
(Chinini sulfas)
Quinini sulfas*
CH=CH2
CH
H3CO
H2SO42H2O
OH
N
(Chinini hydrochloridum)
Quinini hydrochloridum*
XHCl2H2O

(Chinini dihydrochloridum)
X2HCl

.
, . .
.
316
: , , .
. 1. . 23 1
- :
CH=CH2
CH
H3CO
+Br2 89
OH
N
CHCH2
O
CH
Br
Br
OH
89
+ 4NH4OH 89
N
CHCH2
NH
CH
HN
OH
OH
OH
89
+ 2NH4Br + 4H2O
H5C2
OH
N
H
OH
C
N=N
C2H5
OH
N
H
OH
2.
.
3. : Cl
SO42.
317
4. 3 %- 0,1
HCl :
225;
245;
240.
5. , H2SO4,
(
)
(C20H24O2N2)4(H2SO4)2(HI)2I46H2O.
,
HCl, 2
H2SO4.
. 1. , , , .

:
X =
m. F 100 100
m (100 % )
F (
).
2.
:
(C20H24O2N2)HCl+NaOH 89C20H24O2N25+NaCl+H2O
= . .
(C20H24O2N2)2H2SO4+2NaOH 89
892C20H24O2N25+ Na2SO4+2H2O
= 1/2.
. , .
. . ( ).

, .
318
(Papaverini hydrochloridum)
H3CO
H3CO
H3CO
H3CO
6
7
3'
4'
4
3
N HCl
1 2
CH2
2'
1'
6'
5'
6,7--1-(3',4'-)
.
. , . , ,
, .
. 1. Cl.
2. HNO3 ,
. .
3. H2SO4 .
4.
(145147 ).
5. , -.
,
- .
,
:
H!CO OCH! H!CO OCH!

CH
H!CO
H!CO
CH
CH
OCH! SO 2
4
OCH!
.
319
. 1.
(II) , = . .
2. - , , = . .
3. ( ).
. , .
. .
.
(Drotaverine hydrochloride*)
- (Nospanum)
H5C2O
H5C2O
H5C2O
NH
CH
HCl
H5C2O
1-(3',4'-)-6,7-1,2,3,4-
, .
Omnoponum.
( 3 20 %) :
HO
2
1
O
NH
HO
11 10
12
13
*
14 * 9
*
*
5
16
15
*
8
6
7
NCH3
: 3,6-N--4,5--7
320
5 .
, ,
:
HO
H3CO
NCH3
HO
NCH3
HO
. HCl;
140
H5C2O
HO
HO
NCH3
NCH3
HO
()
HCl
(Morphini hydrochloridum)
HO
O
NCH3
HCl3H2O
HO
. , . ,
,
.
. 1. Cl.
2. , , .
321
3. ,
NaOH ( ).
4. ,
- ( ).
5. : 97 99 (2 %- ).
6. FeCl3 ( ).
7. .
8. (III)
. FeCl3
( ):
HO
4
O
NCH3
+ 4K3[Fe(CN)6] 89
HO
HO
HO
89
O
NCH3
HO
NCH3
HO
+ 3K4[Fe(CN)6] + H4[Fe(CN)6]
K4[Fe(CN)6] + FeCl3 89 KFe[Fe(CN)6]5 + 3KCl

9. , - .
. 1. ,
(II) ,
, = . .
2. , = . .
3. - , = . .
. , .
322
. () .
0,5 %-
30 %- .
(Codeinum)
Codeine*
H3CO
H2O
O
NCH3
HO
(Codeini phosphas)
Codeine phosphate*
H3CO
H3PO41,5H2O
O
NCH3
HO
. , . ,
, , .
,
. . ,
, .
. 1. - , .
2. .
H2SO4 FeCl3 , 1 HNO3.
3. HNO3 .
:
) PO43 AgNO3 Ag3PO4;
) ,
NaOH (154157 C).
323
. - , , = . .:
H3CO
H3CO
+ HCl 89
HCl
NCH3
NCH3
HO
HO
:
) , = . .;
) -
(1:2), , = 1/2. .:
H3CO
H3PO4
O
NCH3
2NaOH
Na2HPO4; 2H2O
H3CO
HO
89
O
NCH3
HO
. , .
. () .
(Aethylmorphini hydrochloridum)
H5C2O
HCl2H2O
O
NCH3
HO
. ,
. , ,
.
324
. 1. Cl.
2. H2SO4 FeCl3
, - , 1 HNO3 ( ).
3. . ,
.
. 1.
(II) , = . .
2. - , = . .
. .
. () . .
( )
, .

.
(Apomorphini hydrochloridum)
HO
HO
NCH3
HCl3/4H2O
. , . . , .
. :
325
HO
HO
HO H
HO
HO
H
. HCl ; t

NCH3
H 2O
HO
H NCH3
H
2H2O
HO
89 HO
NCH3
HCl
. 1. HNO3 Cl.
2. HNO3 -
.
3. I2 NaHCO3
- ,
.
4. : 46 52 (1,5 %- 0,02
HCl).
.
(II) , = . .
. .
. .
(Glaucini hydrochloridum)
OCH3
H3CO
H3CO
HCl
NCH3
H3CO
4,5,7,8-
.
326
. -
. , .
. , .
. ;
, ,
.

2,6-, :
OH
N
HO
NH
N
H
12
NH
N
H
, ,
- , , .
(Coffeinum)
Cffeine*
O
H3C
O
NCH3
N
H2O
CH3
1,3,7-
(Theophyllinum)
O
H3C
O
NH
N
H2O
CH3
1,3-
327
(Theobrominum)
O
H
O
NCH3
N
CH3
3,7-
.
, . , . , , , .
, .
, , , ,
.
. , , ,
.
, 9.

(
1 7).
. ,
, .
.
. .
(H2O2, Br2,
HNO3 .) . 12 - :
CH3
O
H3C
2
NCH3
N
CH3
[O]
NH
C=O
NH2
328
O
+
H3C
O
CH3
1,3-
O
H3C
+
OH
N
N
HCl
H3C
N
N
OH
O
N
N
O O
CH3
CH3
CH3
NH !
CH3
1,3-
O
H3C
89
N
O
CH3
H4NO
CH3
O
CH3

()
. : 1) 0,1 %-
, ;
2) 0,1M HCl
C8H10N4O2I4HI, ;
: 1) ,
( ), CoCl2 , , - :
O
ONa
H
N
NCH3
N
NCH3
+ NaOH 89
+ H2O
N
N
N
N
O
O
CH3
CH3
`
ONa
N
NCH3
N
CoCl2
2NaCl
NCH!
N
Co2+
CH!
CH3
2) AgNO3 ( ), 80 .
: 1) CoCl2 329
( );
2) , .
. : 1)
.
Cl4 , , = M. .;
O
H3C
NCH3
N
+ (CH3CO)2O 12
CH3
O
H3C
12
NCH3
+
H3C
+ (CH3COCCH2)
CH3COOH + HClO4 12 CH3COOH+

2 + ClO4
(CH!COCCH ) + CH3COOH2+ 12 (CH3CO)2O + CH3COOH

O
O
O
O
H3C
NCH3
N
H3C
+ ClO4 89
NCH3
N
ClO4
CH3 H
CH3 H
2) , , ,
= 1/4M. .:
O
H!C
O
NCH!
N
H! C
+ 2I2 + HI 89
N
N
CH!
CH!
330
NCH!
_1"_01
. I2
+ 2Na2S2O3 89 Na2S4O6 + 2NaI
( ),

, 0,1 , , = . .:
O
H
OAg
NCH3
N
+ AgNO3 89
O
CH3
NCH3
N
H3C
NH
N
+ HNO3
CH3
O
H3C
+ AgNO3 89
CH3
NAg
N
+ HNO3
CH3
HNO3 + NaOH 89 NaNO3 + H2O
.
. .
.
, , ; (-, ) .
- (Coffeinum-natrii benzoas)
O
H3C
O
NCH3
N
COONa
CH3
. , .
, .
.
,
.
331
. 1. : 1) (234237 C)
;
2) ;
3) ;
4) .
2. :
1) FeCl3 - (.
);
2) Na+ .
. 1.
(. ).
38 40 %.
2.
( 1:1) ( , ), = . .:
COONa
COOH
+ HCl 89
+ NaCl

58 62 %.
- . - ,
.
. , .
. . ,
, .
(Euphyllinum)
Aminophilline*
O
H3C
O
N
N
NH CH2NH2
CH2NH2
N
CH3
1,2-
332
. ,
. , .
; .
. 1. :
1) ;
2) (269274 C)
HCl pH = 45.
2.
- :
CH2NH2
CH2NH2
+ CuSO4 89 Cu
CH2NH2
CH2NH2
SO4
3
. 1. , , = 1/2. .:
CH2NH2
CH2NH2
+ 2HCl 89
CH2NH2
CH2NH2
2HCl
1418, 1822 %.
2.
125130 C , = . .
8085, 7582 %.

.
. CO2,
,
.
. , , . , (12
24 %- ) (2,4 %- ).

.
333
(Diprophyllinum)
O
H3C
NCH2CHCH2OH
N
OH
CH3
7-(2',3'-)-
. , . , ,
.
(Xantinoli nicotinas)
,
O
H3C
O
NCH2CHCH2N
N
N
COOH
CH3
N
CH2
OH
CH3
CH2OH
7-[2'--3'-(N---)-]
. .

:
1) ;
2) ;
3) ;
4) .
(Physostigmini salicylas)
Eserini salicylas*
CH3
H3CNCO
H
CH3 CH3
334
COOH
OH

(Proserinum)
Neostigmine methylsulfate*
H3C
H3C
H3C
OCN
O
CH3
CH3 CH3SO4
. , .
. ,
. , , .

, ,
Pilocarpus.
Pilocarpus jaborandi .
(Pilocarpini hydrochloridum)
H5C2
CH2
NCH3
HCl
O
N
O
---(1--5-)-
-.
. . . , , .
. 1. Cl.
2. (H2O2 + . H2SO4
+ K2Cr2O7), - .

.
335
3. : +88,5 +91 (2 %- ).
4. .
,
HCl. 1 %-
.
5. ():
CH2
H5C2
O
NCH3
N
CH2
C
NaOHN
89
NH OHHCl
NaOH
CH2
H5C2
89
HCl
NCH3
FeCl!
CH2
NCH3
HCl
OH
H5C2
CH2
OHN
Fe3+
OH
. 1.
(II) , = . .
2. , = . .
. ,
.
. () . .
,
-
,
.
HO
H
CCH2NH2
HO
OH
CCH2NH2
H
336
(Ephedrini hydrochloridum)
CHCHCH3 HCl
OH
NHCH3
()1--2--1
. , . ,
, .
, . .
.
. . - .
HO
CCCH3
CCCH3
HO
NHCH3
NHCH3
(-)
( -)
. 1. Cl.
2. CuSO4 :
CHCHCH3
O
NHCH3
Cu
NHCH3
CHCHCH3
- ,
.
3. ()
( ):
337
CHCHCH3
OH
! [Fe(CN)$]
t
O
C
NHCH3
4. : 33 36 (5 %- ).
. 1.
(II) , = . .
2. - , = . .
3. HCl, = . .
. , .
. (, ) .

() , , . m(H2O)n. , .
:
1) , ,
, . .;
2) ;
3) ( ) ;
4)
(, ), ( 2 10 ) ( 10 ).
(Glucosum)
CH2OH
OH
H
H
OH H
H2O
OH
HO
H OH
.
, . 1,5
338
, 95 %- , .
.
.
(C6H10O5)n + nH2O
nC6H12O6
, , 30 , , , 30 , ,
: 61262
. - :
O
CH
HCOH
HOCH
HCOH
HCOH
CH2OH
COO
+2
HCOH
HCOH
NaOOC
HOCH
Cu
HOCH
COOK
OOC
COONa
HCOH
89
+ 3NaOH + 2KOH 89
HOCH
HCOH
COONa
+ 4
HCOH
HCOH
HCOH
+ 2CuOH5 + 2H2O
COOK
CH2OH
52CuOH
Cu2O5 + H2O
,
( ) .
- - 339
,
.
, .
. : .
, - , 100 % -D-(+)-.
:
CH2OH
5
H * OH
H
4 *
* 1
OH H
*
* OH
2
HO 3
H OH
6
-D-(+)-
36 %
CH2OH
H * O OH
H
4 *
* 1
OH H
*
* H
2
HO 3
H OH
6
O
CH
-D-(+)-
63 %
HCOH
HOCH
HCOH
HCOH
CH2OH
D-(+)-
CH2OH
HOCH O
*
5
4 *
*
3
CH2OH
*
HOCH O
OH H
* 1
5
4 *
OH
OH H
*
3
OH
-D-(+)-
OH
*
* 1
OH
-D-(+)-
1 %
-D-(+)- +119;
-D-(+)- +19.
340
D-, 63 % -D-(+)-, 36 % -D-(+)- 1 %

.
+51,5+53. .
, ,
, - - .
- , , ; -
, , , .
. , .
,
.
. 1. .
.
2. .
3. , , ,
=1/2. .

:
O
O
RCH + NaOI + NaOH 89 RCONa + NaI + H2O
:
NaI + NaOI + H2SO4 89 Na2SO4 + I2 + H2O
I2 + 2Na2S2O3 89 2NaI + Na2S4O6
.
. .
. , ,
, ,
.
341
(Sacchrum)
CH2OH
OH
H
H
1
4
OH H
6
HO
HOH2C 1
2
H HO
4 6
CH2 OH
OH H
OH
HC
*
CH OH
HCOH
*
HOCH
*
OHCH
HO
*
HCOH
*
HCOH
*
HC
*
HC
*
CH OH
CH OH
2--D---D-
.
. ,
. 0,5 60 ,
.
184185 ,
,
().

, ,
.
. .
.

:
CH2OH
OH
H
H
1
4
OH H
6
HO
OH
HOH2C 1 O
1
O
H HO
3
4 6
CH2 OH
OH H
342
HCl; H O
t
CH2OH
OH
HOH2C O CH2OH
H
H
89
+
H HO
OH H
OH
HO
H
HO
OH H
H OH
:
[]D20 = +66.

, []D20 = +52,5
[]D20 = 93.
(40). ,
, .
.

.
. , .
. .
. .
, (Saccharum lactis)
CH2OH
HO * O
H
4 *
* 1
OH H
*
* H
2
H 3
H OH
-D-
OH
2
* OH
OH H
4 *
* 1 H O
2
H
H5 * OH
6 CH2OH
3
*
-D-
4--,--,-
,
; 58, 46 %
.
343
.
, . ,
, .
,
,
.
, , ,
.
.
.
. 1. :
CH2OH
O
HO
H
OH H
H
H
H OH
OH
COO
NaOOC
OH
HCOH
HOCH
OH H
Cu
+
2
+
H
HCOH
HOCH
H
H
O
COOK
OOC
CH2OH
+ 3NaOH + 2KOH 89
CH2OH
O
HO
H
89
OH H
H
H
H OH
H
O
OH
COOK
O
HCOH
OH H
C
+
4
+
H
HCOH
OH
H
OH
CH2OH
COONa
+ 2CuOH5 +2H2O
2CuOH
Cu2O5 + H2O
2. +52 +53,5
(5%- ).
20
2 .
, .
. .
.
344
, . ,
,
. .

,
( )
, ( ).
:
. - - , .

.

(-), (N-), ().
- :
1) ( );
2) ( , , );
3) (, );
4) ();
5) ();
6) ( );
7) ();
8) .
, .
, , , .
6- (L-), 2,6- (D-)
3-- (D-, L-).
() , .
,
17 . , , , ,
345
, :
X2
R
2
3
1
4
10
5
11
9
6
12
8
7
13
14
15
OH
X2
CH3
17
16
X3
2
3
X1
10
5
11
9
6
12
8
7
CH3
13
14
15
17
16
OH
X1
17
14.
10.
.

X3
X2
X1
CH3
CH3
OH
CH3
OH
CH3
OCOCH3
OH
.
.
. :
1. :
346
. ,
. ,
.
2. :
96 %- , .
,
.
3. , (III) ;
. .
.
:
1.

.
2. - - .
3.
- .
(III) ; .
. ,
( ,
. .). 2-, , :
1. : , (III) , .
- , - . ,
.
2. :

, - 347
. ,
.

. , ,
Rf . - -.
. ,
. (), , .

,
.
(), (), ()
1 , , 1 1 .
. , .
. .
, , , .
,
, ,
( ), ,
().
() . - - .
OH
HO
COO
OH
HO
COOH
OH
348
OH
HO
OH
COOH
COO
OH
OH
n-
, , -:
CH2OD
O OD
H
H
OD H
H
DO
H OD
D
. .
,
, ( ).
, ; () .
(III) -
- .

.
(Tanninum)
. - , .
, , . .
. 1. 10 %-
.
2. 1 %- (III)
,
.
349
. , , , , .
.
. .
. ; .
,
( 0,5 %- ).

.
,
,
. (
) .
, ().
,
, .
, (, ),
. , : - .
,
:
I. : ( ),
( 15), ( 3).
II. : ( ),
( D).
III. : .
IV. : ( ), ( ),
( ), ( 6),
( 1), ( c), ( 2),
( 12).
350
--
.
. : ,
, . D-.
,
, ( 15).
.
, , , . D- .
, -, . , ,
.
, - ,--,- ()
:
H3C
*
HOCH2CCHCNHCH2CH2COOH
H3C
OH
.
(Acidum ascorbinicum)
Acidum ascorbicum*
HO OH
H
3
* 4
O
HOCH
5*
CH2OH
--2,3--L-
. ,
. , ,
, , .
,
.

.
351
3;
(. ).
:
1) ( );
2) , - :
HO OH
H
[O]
[H]
O
HOCH
O O
H
1)
[O]
O
HOCH
2)
O
H
CH2OH
CH2OH
. 1. :
HO OH
H
O
HOCH
O O
H
O
+ 2AgNO3 89
+ 2Ag5 + 2HNO3
O
O
HOCH
CH2OH
CH2OH
2. 1
2,6- :
OH
OH
CH2OH
Cl
O O
H
=
O
HOCH
HO OH
H
89
O
HOCH
Cl
CH2OH
NH
O
Cl
Cl
OH
352
3. , [Fe(CN)6]3 [Fe(CN)6]4, Fe3+ Fe2+, Cu2+

Cu+, MnO4 Mn2+, NO3 NO2, AsO43 AsO33,
NO6, - .
4. (II)
,
:
HO OH
H
2
O
HOCH
+ FeSO4 + 2NaHCO3 89
CH2OH
O OH
H
89
O
HOCH
CH2OH
Fe2+ + Na2SO4 + 2CO26 + 2H2O
. 1. , , , = 1/2. .:
O O
H
HO OH
H
3
O
HOCH
+ KIO3 89 !
O
HOCH
+ KI + 3H2O
CH2OH
CH2OH
:
KIO3 + 5KI + 6HCl 89 3I2 + 6KCl + 3H2O
2. , , ,
= . .:
353
HO OH
H
+ NaOH 89
O
HOCH
NaO OH
H
O
O
HOCH
CH2OH
+ H2O
CH2OH
3. , , = 1/2. .:
O O
H
HO OH
H
+ I2 89
O
HOCH
O
HOCH
+ 2HI
CH2OH
CH2OH
4. 2,6-, = 1/2 M. .
.
5. - (, .),
= 1/2 M. .
. .
, , .
. (), , , .
(Calcii pangamas)
O
HCOH
HOCH
HCOH
Ca2+H2O
HCOH
CH2OCCH2N
O
CH3
CH3
2
354
. ,
. ,
.
. 1.
-.
2. Ca2+.
3. Fe3+ .
4.
.
5. ( ):
HCOH
HOCH
Ca2+
HCOH
HCOH
CH2 OCOCH2 N
NH OHHCl
CH3
CH3
+ 2CH2OH(CHOH)4COONa + 2
H3C
H3C
NCH2C
H3C
NCH2C
H3C
O
NHONa
FeCl!
NHONa
89
Ca(OH)2 +
NaOH
H3C
H3C
HCl
NCH2 C
O
NHO
F3+ + 3NaCl
. , , , 25 % 6 %
, :
355
1)
(3,64,2 %);
2) (5,87,4 %);
3) ( 2,2 %);
4) (1115 %) .
. , .
. , , . .
,
.
(Calcii pantothenas)
H3C
*
HOCH2CCHCNHCH2CH2COO
H3C
OH
Ca2+
2
D-(+)-,--,--N-'-
. .
, .
. 1. Ca2+.
2. (-):
H3C
HOCH2CCHC=NCH2CH2CO
H3C
OH
ONa
Cu
H3C
HOCH2CCHC=NCH2CH2CO
H3C
OH
ONa
3. , --,- . 356
,
(III)
:
H3C
Ca2+
HOCH2CCHCNHCH2CH2CO
H3C
OH
4NaOH
t
H3C
89 Ca(OH)2 + 2 HOCH2CCHCONa + H2O +
H3C
OH
+ 2 H2NCH2CH2CONa
H3C
3 HOCH2CCHCONa
H3C
FeCl!
HCl
OH
H3C
89
HOCH2CCHCO
H3C
OH
Fe3+
3
4. :
H3C
Ca2+
HOCH2CCHCNHCH2CH2COO
H3C
OH
2HCl
HOH
CH3
89 2H2NCH2CH2COOH + 2
CH3
3
H3CC
H2C
H2C
CHOH
O
CHOH
O
H3CC
NH2OHHCl
NaOH
357
H3C
89 3 HOCH2CCHCNHONa
H3C
OH
FeCl!
HCl
H3C
89 HOCH2CCHCNHO
H3C
OH
Fe3+
!
5. +25 +28 (5 %- ).
. .
. Ca2+ (8,28,6 %) , (5,76,0 %)
.
. ,
.
. , , , ,
, .

(
A) ( D).
,
, .
1909 . 1928 , ,
, . -, - -.
D, , , .
D: D1D7,
, - . D2 () D3 ().
D2 D3 , , , .
.
.
358
(Retinoli acetas)
Axerophtholum aceticum*
H3C
CH3
CH3
CH3
CH2OC
O
CH3
CH3
-9,13--7-(1,1,5--5--6)-7,9,11,13--15
. - .
.
, 95 %- , ,
.
. (III) .
. -.
. , ,
,
, +5 .
, +10 .
. ,
, . , , , . .
(Ergocalciferolum)
CH3
H3C
CH2
CH3
CH3
CH3
HO
24--9,10--5,7,10(19),22--3 -
. , .
359
, , , , .
, .

- - .
D2 . ,
.
.
(III)
- . .
. ,
, ,
.
. (0,5 %-) (0,125 %-) D2
, , .
D
.

2--1,4 ( ).
.

.
(Vikasolum)
O
CH3
SO3Na3H2O
O
2,3--2--1,4--2-
. ,
. ,
, .
360
. 1. 1 :
O
CH3
SO3Na
CH3
NaOH
+ Na2SO3 + H2O
2--1,4- , (104
107 ).
2. :
O
CH3
CH3
SO3Na + H2SO4 89 2
+ 2SO26 +
+ Na2SO4 + 2H2O
3. Na+.
. 2--1,4--3-.
( 2 %).
2--1,4--3- - (
).
. , , -, = 1/2. . 2--1,4-,
.
2--1,4-, 0,1
:
O
CH3
SO3Na
O
CH3
NaOH
+ Na2SO3 + H2O
O
361
OH
CH3
CH3
Zn
HCl
OH
OH
O
CH3
CH3
+ 2Ce(SO4)2 89
+ Ce2(SO4)3 + H2SO4
OH
O
2+
Fe
3+
+ Ce4+ 89 Fe
+ Ce3+
. , .
. .
, .

, ( ), (, , , , .),
, . , ,
, , .

.

.

6--2--2-(4',8',12'-)-:
362
CH3
HO
6
7
13'
12'
11'
10'
6'
7'
9'
CH3CHCH2CH2CH2
1'
2'
3'
4'
5'
8'
CH2CH2CH2CHCH2CH2CH2CH
O
CH3
1
CH3
CH3
2

; 7 . -. .
, (),
. , -
, .
(Tocopheroli acetas)
O
H3C
CH3
CH3
CO
H3C
CH2(CH2CH2CHCH2 )2 CH2
O
CH3
CH3CHCH2
CH3
CH3
()-2,5,7,8--2-(4',8',12'-)6-
. -, , ,
. ,
95%- , , .
.
. 1. , ,
- (-):
O
H3C
CH3
CO
H3C
HNO!
R
O
CH3
CH3
O
H3C
R
O
CH3
CH3
-
363
2. KOH ( ), .
3. (III)
--:
CH3
H3C
CH3
CH3
HO
H3C
[ O H ]
CH3
CH2
K ![Fe(CN) $]
CH2
O
CH3
H3C
R
O
CH3
CH3
. , , , = 1/2. .:
O
H3C
CH3
CH3
CO
R
O
H3C
CH3
HO
HOH
H2 SO4
H3C
CH3
R
O
CH3
CH3
+ CH3COOH
CH3
HO
H3C
R
O
CH3
+ 2Ce(SO4)2
CH3
CH3
O
89
H3C
O
CH3
C
OH
n-
364
R
CH3
+ Ce2(SO4)3 + H2SO4
4+
Ce
H2 SO4
NH
HSO4

(- )
.
, .
. ,
, , .
. , , , ,

0,32 % -, , 0,05;
0,1 0,2 - 1 , .
(Rutinum)
HO
HO
HO
O
OH
CH!
O
HO OH
CH2
O
O
OH
HO
3H2O
OH
OH
3- , 3-3,5,7,3',4'-
. -
. , , ,
, , ,
, .

,
.
. 1. 1M
- .
:
365
OH O
NaO
OR
HO
OR
NaOH
CH
ONa
NaO
OH
OH
ONa
ONa
2. ,
, ( ).
:
OH O
OH
OR
HO
OR
Mg
HCl
OH
HO
OH
O
Cl
OH
OH
3.
.
4. -
259 362,5 .
. .
. , .
. ,
.
- , ,
. . ,
, .

, , ,
( ) ( 6).
, -, 18671870 . 19371938 . 366
, ,
. ,
.
6 : (), , :
HO
CH2OH
N
H3C
O
H
CH2OH
[O]
HO
CH2OH
N
H3C
[H]
NH!
CH2NH2
HO
CH2OH
89
H3C
, .
(Acidum nicotinicum)
COOH
N
-3-
. , . 95 %- , , .
(
) ( ).
. 1. :
COO
COOH
2
+ CuSO4 89
Cu2+ + H2SO4
2
2. Na2CO3 :
367
COOH
Na CO!
+ CO26
N
N
3. 2,4-
(. ).
. 1. , , , = . .:
COOH
COONa
+ NaOH 89
+ H 2O
N
N
2.
. ,
CuSO4 , , = 2. .:
COONa
2
COO
+ CuSO4 89
N
.
Cu + Na2SO4
2
2CuSO4 + 4KI 89 Cu2I25 + I2 + 2K2SO4

I2 + 2Na2S2O3 89 2NaI + Na2S4O6
.
. , .
. .
, , ,
, , .
: , .
, ,
.
(Nicotinamidum)
O
NH2
N

. , . 368
, , .
.
. 1. :
CONH2
Na2CO3
t
+ CO26 + NH36
2.
:
CONH2
COONa
NaOH
+ NH36
3. .
. , , = . .:
CONH2
N
+ HClO4
CONH2
CH!COOH
+
ClO4
H
.
. , .
. , .
(Pyridoxini hydrohloridum)
CH2OH
HO
H3C
CH2OH
HCl
2--3--4,5--()-
. ,
- . , 95 %- , .
369
. 1. (III)
, ( ):
CH2OH
HO
H3C
CH2OH
Cl2FeO
CH2OH
+ FeCl3 89
H3C
CH2OH
+ HCl
2. 2,6-,

.
:
CH2OH
HO
H3C
CH2OH
N
Cl
+ ClN
HCl
Cl
CH2OH
HO
89
H3C
CH2OH Cl
N
O
Cl
3.
. , :
CH2OH
HOH2C
OH
N
CH3
1. N
R Cl
2. ZnCl2
HOH2C
89
R
370
N=N
H2C
N
Zn
O
CH3
4. -.
. . 2,4-
,
:
H2CO
HOH2C
O
N
OCH2
CH2OH
O
CH3 H3C
H+

.
. 1.
(II) ,
, = . .:
CH2OH
HO
2
H3C
CH2OH
HCl + Hg(CH3COO)2 + 2HClO4
CH!COOH
CH2OH
HO
&' 2
H3C
CH2OH
N
HClO4 + HgCl2 + 2CH3COOH
.
2. , , , = . . Cl.
-,
17,1 17,35 %.
CH2OH
HO
H3C
CH2OH
HO
CH2OH
N
HCl + NaOH 89
H3C
CH2OH
N
+ NaCl + H2O
371
. , .
. , , .
- ( 1 ) ()
(), :
CH3
N
H3C
CH2 N
NH2
CH2CH2OH
ClHCl
,
, ().
(Thiamini bromidum)
CH3
CH2 N
N
H3C
NH2
CH2CH2OH
BrHBr1/2H2O
4--5---N-(2'--4'--5'-)
. , . , , .
. 1.
,
, -:
372
CH3
CH2 N
N
N
H3C
NH2
H3C
O CS
NH2
HH
NaOH
CH3
CH2 N
&'
BrHBr
CH2CH2OH
CH2CH2OH
89
H3C
CH3
N
N
K![Fe(CN)]$
CH2CH2OH
2. -

- .
. 1. . :
SiO212WO32C12H17BrN4OS. , 0,25 ( ), .
2. , ,
, = . .
3. , , = 1/2. .:
(C12H17N4OS)+BrHBr + 2AgNO3 89
89 2AgBr5 + (C12H17N4OS)+NO3HNO3
4. .

- , :
CH3
CH2 N
N
H3C
NH2
CH2CH2OH
373
BrHBr + NaOH 89
CH3
CH2 N
89
H3C
NH2
CH2CH2OH
Br + H2O + NaBr
, 0,1 0,1 NH4SCN

()
:
3NH4SCN + FeNH4(SO4)2 89 Fe(SCN)3 + 2(NH4)2SO4
0,1 :
CH3
CH2 N
N
H3C
NH2
(CH2)2OH
CH3
CH2 N
89 2AgBr5 +
H3C
NH2
Br + NaBr + 2AgNO3 89
(CH2)2OH
NO
3 + NaNO3

() :
3AgNO3 + Fe(SCN)3 89 3AgSCN5 + Fe(NO3)3
, , = . .
. , . , :
CH3
N
S
CH2CH2OH
374
(Thiamini chloridum)
CH3
CH2 N
N
N
H3C
NH2
CH2CH2OH
ClHCl
4--5---N-(2'--4'--5'-)
. . , 95%-
, , , . .
. 1. .
2. -.
.
(II) , , = 1/2. .:
CH3
CH2 N
N
H3C
NH2
CH2CH2OH
+ Hg(CH3COO)2
CH2 N
N
H3C
NH2
CH3COOH
CH3
89
ClHCl + 2HClO4 +
CH2CH2OH
ClO4HClO4 +
+ HgCl2 + 2CH3COOH
.
.
. .
.
, , , .
,
.
375
(Cocarboxylasum)
Cocarboxylase*
CH3
CH2 N
N
H3C
NH2
CH2CH2OPOPO HCl
OH
OH

.
. ,
- .

( 2)
. B2
, ,
, (. flavus
).
, , ,
; , ; .
(Riboflavinum)
CH2(CHOH)3CH2OH
H3C
H3C
N
N
O
6,7--9-(1-D-)-
. - , . . , 95 %-
, , , , .
. 1. - -.
,
, :
376
CH2(CHOH)3CH2OH
H3C
H3C
N
N
O
NaHSO!
CH2(CHOH)3CH2OH
H
89
H3C
H3C
N
H
N
N
O
2. : 110 130 (0,5 %-

- ).
3.
,
.
4.
-
.
. ,
:
CH3
H3C
H3C
N
N
O

( ) .
. 1. .
2. .
3. .
4. , = 1/2. .
5. , = . .
. .
. ,
, , .
377
,
( ), , , ; (, , ),
, .
, .
(Acidum folicum)
CH2CH2
OH
N
N
H2N
CH2NH
CONHCH
COOH
COOH
N-{4'-[(2--4--6)-]-}-L-(+)-
. -
. , . , 95 %- ,
, , ,
,
, .
: 2--4- (), - .
:
, 4.
. 1.
-6- (2--4--6 ),
-:
OH
N
N
H2N
COOH
2. - .
3.
. ,
378
, , (III) -.
:
N
RH2C
O
H2N
N
Me
O
CH2R
NH2
.
.
- , N-(1-)- . :
OH
H2N
CH2NH
CNHCH
H2N
.
N
N
COOH
[O]
COOH
N
OH
89
CH2CH2
COOH
+ H2N
CH2CH2
CNHCH
COOH
COOH
2KMnO4 + 5NaNO2 + 6HCl 89

89 5NaNO3 + 2KCl + 2MnCl2 + 3H2O
O
H2N
COOH
CNHCHCH2CH2COOH
O
+
89 N3N
NaNO
HCl
COOH
CNHCHCH2CH2COOH Cl
379
NaNO2 + H2NSO2OH 89 NaHSO4 + H2O + N26
O
+
N3N
NHCH2 CH2NH2
COOH
CNHCH
COOH Cl
CH2CH2
NHCH CH NH
N=N
COOH
CNHCH
89
COOH
CH CH

7,8- :
OH
N
N
H2N
OH
CH2R
[O]
[H]
H2N
CH2R
N
H
7,8-
, .
. , .
. ,
, , .

( 12) , ,
. , 12 , .
12 , , .
12
.
380
.
, 5,6-, , , ,
.
( ) .
5,6- 3
. .
(Cyancobalaminum)
H
H
OH
CH OH
H!C
N
N
H!C
O=PO
H NOC
O
HC
HC
H!C
CH!
CONH
CH
H NOCH C
C
B
H!C
CH
CHCH!
CH
H!C
CH!
Co
N
H NOCH CH C
C3N
CH!
H NOCH C
CO
N
D
CH!
NH
CH CH
CH!
CH CONH
. - , , . , 95 %- , , , .
. 1. - .
381
2. 1--2-3,6- .
. -.
. , ,
.
. , , , , .

,
, .
50 .
(
, ). .
, ,
, , . , , ,
( , ,
, ).
(
, ).

. : , , ().

:
I
HO
I
*
O
I
CH2CHCOOH
NH2
3,5,3',5'- ()
382
I
HO
I
*
CH2CHCOOH
NH2
I
3,5,3'-
L-, , .
(Thyreoidinum)
. - ,
.
. L-
L-3,5,3'-.
. 1. .
.
2. , . , ,
. , , - .

. , 0,2 % . , , .
.
. .
.
:
5HI + 6KMnO4 + 9H2SO4 89 5HIO3 + 6MnSO4 + 3K2SO4 + 9H2O
HI + 2KMnO4 + H2SO4 89 2MnO25 + HIO3 + K2SO4 + H2O

:
383
2KMnO4 + 5NaNO2 + 3H2SO4 89

89 2MnSO4 + 5NaNO3 + K2SO4 + 3H2O
5MnO2 + NaNO2 + H2SO4 89 MnSO4 + NaNO3 + H2O
:
O
2 HNO2 + H2NCNH2 89 CO26 + 2N26 + 3H2O

() ,
. , , ,
:
HIO3 + 5HI 89 3I2 + 3H2O
I2 + 2Na2S2O3 89 2NaI + Na2S4O6
0,170,23 % .

, .
. .
. , , , , .

.
,
, .
(Adrenalini hydrotartras)
Epinephrine bitartrate*
HO
HO
OH
*
CHCH2NHCH3
HOCHCOOH
HOOCHCOH
()-1-(3',4'-)-2-
384
(Noradrenalini hydrotartras)
Levarterenol bitartrate*
HO
HO
OH
HOCHCOOH
CHCH2NH2
H2O
HOOCHCOH
()-1-(3',4'-)-2-
(Mesatonum)
Phenylephrine hydrochloride*
HO
OH
CHCH2NHCH3HCl
1-(-)-2-
. ,
, , . , . , .
.
. :
O
CCH2Cl
ClCCH2Cl
HO
OH
HO
NH CH!;
( NH3

)
OH
-3,4-
CCH2 N
89
HO
OH
385
H
CH3
HCl
[H]
CH(OH)CH2N
89
H
CH3
HCl
HO
OH
, .
. 1. (III)
- , 1 -, -.
(III) .
2. 0,1 ,
= 3,56 6,5. , - ( = 3,56) - ( = 6,5) .
(-
) , = 6,5:
HO
HO
CH(OH)CH2N
H
R
I2
pH = 3,56
() 6,5
CHOH
CH2
R
R = H, CH3
3. - .
4. - .
5.
-
, , , .
6. .
7. - :
386
HO
OH
CH3
HO
HO
4H
CH(OH)CH2NH
OH
CH3
8.
,
3,4- :
HO
HO
CH(OH)CH2NHR 89
HO
CCH3 + RNH26
HO
R = H, CH3
9. ,
.
. , .
. , , = . .:
COOH
HO
HO
CH(OH)CH2N
H HOCH
+ HClO4 89
R
HCOH
COOH
COOH
HO
89 HO
CH(OH)CH2N
H
HOCH
H ClO4 +
HCOH
R
COOH
R=CH3, H
387

.

, ,
= 1/6 . .:
HO
CHCH2NHCH3 + 3Br2 89
OH
HO
Br
89 Br
CHCH2NHCH3 + 3HBr
Br
OH
Br2 + 2KI 89 I2 + 2KBr

I2 + 2Na2S2O3 89 2NaI + Na2S4O6
(II)
,
, .
. , .
0,1 % [
(IV)].
. , () . ,
, ,
, . 0,1 %-
0,51 %- .

() , ,
388
, (), () (),
).
. :
18
12
X2
11
19
1
2
X1
CH3
10
5
C
H
H
B
CH3
13
14
17
16
15
, 10 13, . R
( 8, 9, 14) -
- .
, ( ).
-,
(-), , - (-), .
,
.
,
.
;
( ).
, ,
.
.

, , ,
, , .
389
, 3,
, , 2,4-,
(, -).
NH OH
NHNH
NHNH
NO
O
CNHNH
NO
N
HON
NHN
O2N
NO2
O
NHN
CNHN
( , ) ( ).
, 3 17
,
(, ) :
ROH +
CH3C
CH3C
O 89 ROCCH3 + CH3COOH
O
390
ROH +
O
Cl
89 ROC
+ HCl
,
(, ), :
OH
O
O
C
CH2OCCH3
NH OHHCl
NaOH
O
OH
CCH2OH
+ CH3C
3 CH3C
O
NHONa
H ; FeCl!
CH3C
O
NHO
O
NHONa
Fe3+ + 3NaCl
3

-
.
,
,

. .
-,
, , . .

, .
3 ,
4. 17 -
.
: .
391
. (- )
11 17.
,
, ().
() ()
.
, .
, , . ,
, .

, , : - , , .
.
, , . ,
1 .
9-, 16- . , 2040 .
(),
9- 6-, ( 150300 ). , ,
, .
.
, , .
, - . . .
.
-
(I) .
- ,
:
392
CCH2OH
COH
[O]
, ( ), - , (III).

:
CCH2OH
O
+ H5C6C
COH
O
NNC6H5
+
N=NC6H5
+ H5C6C
Cl
89
NNHC6H5
N=NC6 H5
.

(Desoxycorticosteroni acetas)
Desoxycortone acetate*
CH3
H3C
H
H
CCH2OCCH3
O
-4--21--3,20-21-
. (- ),
-
(21-).

- . , ( ).
393
. -.
0,5 %-
.
. , .
. , , , .
(Cortisoni acetas)
Cotisone acetate*
O
H3C
H
H
O
O
CH3 OH
CCH2OCCH3
H
O
-4--17,21--3,11,20-21-
. ( 3); ( ); - (21-).
( ); 1520 -
( ).
. - = 238 .
.
, .
(Hydrocortisoni acetas)
O
HO
H3C
H
H
CH3 CCH2OCCH3
OH
H
O
-4--11,17,21--3,20-21-
. ;
( ).
394
(21-).
(
3).
- ,
( ).
.
.
. -.
(Prednisolonum)
Prednisolone*
O
HO
H3C
H
H
CH3 CCH2OH
OH
H
O
-1,4--11,17,21--3,20
. ( );

( 3).

- ( - 365 );
, - ( ).
.
.
. -.
(Dexamethasonum)
CH2OH
HO
H3C
H
F
CH3 C=O
OH
H
CH3
O
16--9-
395
.
( 3). 5 -
, ( ).
- - ,
.
. .
. -.
(Triamcinolonum)
Triamcinolone*
CH2OH
HO
H3C
CH3 C=O
OH
H
OH
F H
O
9--16-
. . .
, , .
- -.
. .
. -.
(Fluocinoloni acetonidum*)
(Synaflanum)
CH2OH
HO
H3C
O
CH3 C=O
O
H
O
F H
CH3
CH3
6, 9--16--16,17-
396
. -, .
. .
(Flumetasoni pivalus*)
CH2OCOC(CH3)3
HO
H3C
O
CH3 C=O
OH
H
CH3
F H
F
6,9--16--21-

( ) , ,
10 13,
3 4. ,
, 11, , , 17
- () - () ().
(Progesteronum)
CH3
CH3 C=O
H3C
H
H
O
-4--3,20
. . , , .
397
. -, .
. ( ).
- , -.
2,4-, (
3).
.
.
. 2,4
= 241 .
. , .
. .
1 2,5 %- .
(Praegninum)
Ethisterone*
H3C
H
H
CH3 OH
C3CH
H
O
-4--20--17--3, 17-
. . ,
, .
. -, . . ,
( ).
( 3).
. 1. .
, , , = . .:
398
OH
OH
C3CH + AgNO 89
3
C3CAg + HNO
3
HNO3 + NaOH 89 NaNO3 + H2O

2. = 241
.
. , .
. . 56 ,
,
.

() . ,
, , ,
.
, .
,
,
.
.
(17-),
, -
.
, ,
. ,
1. 100
.
3 (-) 4 5. 399
10. , (19- ) , ,
.
715 .
(Testosteroni propionas)
CH3 H
H3 C
H
H
O
OCCH2CH3
O
-4--3--17
. . , , .
. ( 3) ,
.
-
(17-).
.
.
. -.
. ,
.
. , ,
.
(Methyltestosteronum)
H3C
H
H
CH3 CH3
OH
H
O
17--4--17--3
. . , ,
, , .
400
. - ;
-
( ).
( 3)
( 17).
. .
. ,
.
. . 23
, ,
.
(Methandrostenolonum)
Metandienone*
H3C
H
H
CH3 OH
CH3
H
O
17--1,4--17--3
. , . ,
, , .
.
( ). 2,4- - ( 3).
. () , ( 0,01 %)
.
. -.

.
. ,
.
.
, , ,
.
401
(Methylandrostendiolum)
Methandriol*
H3C
H
H
CH3 OH
CH3
H
HO
17--5--3,17
. . , ,
.
.
- ; ( ). .
. .
. .
(Phenobolinum)
Nandrolone phenylpropionate*
CH3
H
H
OCCH2CH2
O
O
17--19--4--3--17-,
19-
. ,
. , , .
. (95
99 C), .
. -.
. .
. .
402
18
11
1
2
3
9
10
5
12
CH3
13
14
17
16
15
, , . 3
. , , 10.
17 () (, ).
:
CH3 O
CH3 OH
H
H
H
H
HO
HO
,
.
( ) , .
, , 17
. .
, - .
403
(Oestradioli dipropionas)
Estradiol dipropionate*
CH3
H
O
OC
C2H5
CO
C2H5
-1,3,5(10)--3,17-
. . , .
. - -.
, .

.
, .
. , . 0,1 ,
0,1
, = 1/2. .
. , .
. . 0,1 %- 23
.
(Aethinyloestradiolum)
Ethynilestradiol*
H
H
CH3 C3CH
OH
H
HO
17--1,3,5(10)--3,17
. -
. , 404
, , , , .
. , - ( ).

- . - -, .
( ).
.
.
. (. ),
:
HOO2S
HOO2S
N=N
H
H
CH3 C3CH
OH
H
HO
N=N
. .
. . . .

, ,
, . ,
. , . . ,
( 3 17)
1,1, - 1,2, -
1,22 . - , 0,75, .
405
(Synoestrolum)
Hexestrolum*
C2H5
HO
CHCH
OH
C2H5
-3,4--(-)-
(Diaethylstilboestrolum)
C2H5
HO
C=C
OH
C2H5
-3,4--(-)--3
. ( ) (
) .
. , .
. 1.
( )
- ( ).
, .
2. (.
).
- ;
-, .
3.
(III) .
,
, .
4.
-.
5.
. 406
(),
.
. 1. .
( ) .
, , = 1/2. . .
:
C2H5
HO
CHCH
OH + 2
CH3C
CH3C
C2H5
O
O 89
O
C2H5
89 H3CCO
CHCH
O
OCCH3 +
C2H5
+ 2CH3COOH
O
CH3C
CH3C
O + H2O 89 2CH3COOH
O
CH3COOH + NaOH 89 CH3COONa + H2O

.
2. , = 1/8. .:
5KBr + KBrO3 + 3H2SO4 89 3Br2 + 3K2SO4 + 3H2O
C2H5
HO
CHCH
OH + 4Br2 89
C2H5
407
Br
Br
C2H5
89 HO
CHCH
OH + 4HBr
C2H5
Br
Br
.
3.
:
+
N3N
C2H5
HO
CHCH
HSO4 89
OH + 2
C2H5
SO3H
C2H5
89 HO
N=N
CHCH
C2H5
SO3H
OH
+ 2H2SO4
N=N
SO3H
. , .
. .
- , .
2
0,1 23 %- (
).
,
(, ,
, , .). , . ,
:
408
COOH
CH3
10
11
12
13
14
15
16
17
18
19
20
,
.
E, F, A, B ( , F, A, B).
. ,
. -, -, -, , .
. :
1. ( ,
.).
2.
.
3. .
. : , , , () . -.

,
(, ,
), .
.
, -
, ,
, , . 1 2 ; ,
F ; 1
2, , .

, , , ) ,
409
,
(, , , ) .
. 80-
IX , Penicillium
notatum.
. 1928
. . . 19341940 .
:
;
;
.
, , - ,
, .
:
1. ( ,
.).
2. ( ).
3. (,
, .).
4. :
;
(, , ,
);
( );
( ).
5.
(, , ).
6. (, .).
7. :
;
;
-5,8-;
.

, , 410
, .

:
1. (Penicillium)
(Streptomyces) . , , , .
, .
:
;
;
();
.
2. ( ).
3. .
( ,
, .).
, ,
- .
.
.
,

-.
.

, .

().
, - . 1
.
411
, ,
, .
, /.
: ;
(, , );
( ,
).

()

():
7
8
5a
11a
6a
10a
10
11
4
4a
12a
12
3
2
. : Streptomyces rimosus Streptomyces

aureofaciens.

.

(Tetracyclinum)
H3C
8
9
10
OH
5a
11a
4a
12a
6a
10a
11 12
OH O
CH3
OH 1
OH O
CH3
OH
CNH2
O
4--1,4,4,5,5,6,11,12--3,6,10,12,12-6--1,11--2-

(Tetracyclini hydrochloridum).
412
(Doxycyclini hydrochloridum)
H3C
OH O
CH3
OH N
H
CH3
OH
OH
OH O
CNH2 HCl1/2C2H5OH1/2H2O
O
4--1,4,4,5,5,6,11,12--3,5,10,12,12-6--1,11--2-

(Methacyclini hydrochloridum)
H2C
OH N
OH O
OH
OH O
CH3
CH3
OH
CNH2 HCl
O
4--1,4,4,5,5,6,11,12--3,5,1012,12-6--1,11--2-
:
(+) ;
(+ , 1, 2).
.
- ,
, .
.
- , . , , ,
. 4,
10 3 12.
413
. 1. , :
H3C HO
OH O
OH
OH O
CH3
H3C
CH3
OH
. H SO"
CH3
CH3
OH
OH
OH OH O O
CONH2
CONH2
2. -.
.
3. .
4.
(III) ( 10).
5. (II),
.
6.
-.
7. .
8. .
9. -
, -, , .
:
R
N! N Cl`
N=N
OH
OH
. 1.
.
1 = 1 , 1,0 =1 000 000 .
2. -, .
. ,
, .
414

4-
. ,
.

.

, . ,
.
H3C
OH O
OH
OH
OH O
CH3
CH3
OH
H3C
[OH `]
CONH2
OH O
OH
O O
CH3
CH3
OH
CONH2
. ,
, , .
, ,
, .
, .
(),
. (, ,
), (12 ).
, , ,
.
. ,
, . .

, , Al, Mg, Ca.
,
.
415
,
, , ,
1947
Streptomyces venezuelae, 1949 .
, , .
,
, .
(Laevomycetinum)
(Chloramphenicolum)
NHCOCHCl2
O2N
CHCHCH2OH
OH
D-()--1---2--1,3
(Laevomycetini stearas)
NHCOCHCl2
O2N
CHCHCH2OC(CH2)16CH3
OH
O
D-()--1---2-1,3-3-
(Laevomycetini succinas sulubile)
NHCOCHCl2
O2N
CHCHCH2OC(CH2)2CONa
OH
O
O
D-()--1-n--2-1,3-3-
2
: D- L--, D-
L--, :
416
H H
NHCOCHCl2
*
CCCH2OH
CCCH2OH
OH H
OH NHCOCHCl2
.
- D .
D () L (+) - ,
, (
50 % ).
- ,
.
. -,
:
O
O2N
CCH3
Br
O2N
CCH2Br
(CH ) $N "
HCl
---
89 O2N
CCH2NH2HCl
(CH!CO) O
O
---
O
HC
89 O2N
CCH2NHCCH3
O
---
NHCOCH3
89 O2N
CCHCH2OH
[H]
O
-----
NHCOCH!
89 O N
CHCHCH OH
OH
D,L--1--2--1,3
417
HO
HCl
NH2HCl
89 O2N
CHCHCH2OH
NaOH
OH
D,L--1--2--1,3-
NH2
89 O2N
CHCHCH2OH
OH
D,L--1--2--1,3

D- . D-- :
NH2
O2N
CHCHCH2OH
Cl2CHCOCH3
OH
CH3OH
D-()--1--2--1,3
NHCOCHCl2
89 O2N
CHCHCH2OH
OH
.
- .
.
. , .
.
, , .
. ; ,
.
5 %- : +18
+21() +15 +20 ( ),
11 12,6 ( ,
).
. 1. 418
.
, , ( ),
-
:
NHCOCHCl2
CHCHCH2OH + 4NaOH 89
O2N
OH
OH
89 N
CCHCH2OH +
ONa
OH
CCOONa +
+ NH36 + H2O + 2NaCl

, Cl.
2.
, ,
:
NHCOCHCl2
O2N
CHCHCH2OCO(CH2)16CH3
HCl
HO
OH

NHCOCHCl2
89 O2N
CHCHCH2OH + HOOC(CH2)16CH3

OH
3.
:
419
NHCOCHCl2
O2N
CHCHCH2OH + 5Zn + 4H2SO4 89 ZnCl2 +

OH
O
NHCCH3
+ 4ZnSO4 + 2H2O + H2N
CHCHCH2OH
NaNO
HCl
OH
1---2--1,3
NHCOCH3
+
OH
CHCHCH2OH Cl
89 N3N
NaOH
OH
NHCOCH3
89
N=N
ONa
CHCHCH2OH
OH
4. -
- -
, , ,
:
ONa
N=CCHCl2
O2N
CHCHCH2OH
O
Cu
O
O2N
CHCHCH2OH
N=CCHCl2
ONa
420
5. -,
.
. 1.

, = . .:
NHCOCHCl2
O2N
CHCHCH2OH
OH
89 H2N
Zn
HCl
NHCOCH3
CHCHCH2 OH
NaNO
HCl
OH
NHCOCH3
+
CHCHCH2OH Cl
89 N3N
OH
2. = 278 (), 272
( ) 275 ( ).
3. , .
(. ).
0,01 (),
. ,
, = 2. .
4. , .
. (II) , -

, , ,
= 2. .:
2C11H12Cl2N2O5+CuSO4
NaOH
(C11H12Cl2N2O5)2Cu
(C11H12Cl2N2O5)2Cu+H2SO4 892 C11H12Cl2N2O5+CuSO4

2CuSO4+4KI 89I2+Cu2I25+2K2SO4
I2+2Na2S2O3 892NaI+Na2S4O6
.
421
5. .
, 2 ,
, = 1/2. .
6. .
7. .
. ,
= 1/6. .
8. , , = 1/4. .
. ,
.
. , , ,
, .
810 . , .
. ,
.
.

6- (6-), () - () :
H2N
O
B
7
S1
A
N4 3
6-
CH3
CH3
COOH
.
,
. . , .

.
.
Penicillium notatum Penicillium chrysogenum.
422

- , .

8090 %
, ,
- .
,
, 6-.
6-. :
O
O
CH!
CH!
S
S
RCCl
CH!
CH!
RCHN
HN
HCl
O
O
COOH
COOH
N
N

6-
O
S
RCHN
O
CH3
CH3
COOR1
R1
CH2C6H5
Na(K)
()
Benzylpenicillinum
natrium (kalium)
CH2OC6H5
(Penicillium V
)
Phenoxymethylpenicillinum
CH2C6H5
NH
C H#
COO(CH ) NH
C H#
423

Benzylpenicillinum
novocainum
R1
CHC6H5
3H2O
NH2
H!C
C$H#
H2O
CHC6H5
Ampicillinum
-
Na

Oxacillinum natrium

3--5-4-
Na

Carbenicillinum
dinatrium

6-(2-)
Na

Azlocillinum natrium

6-[D-2-(2-1-1-)2-]
Na

Carphecillinum natrium

6-(L-)
COONa
O
HCHNCN
O
NH
C6H5
CHC6H5
COOC6H5
424
( ).
. 1. (II) ()
(III) ( )
- :
O
RCHN
O
S
N
CH3
CH3
COOH
NH2OHHCl
NaOH
O
RCHN
89
O C HN
NHONa
89
CH3
CH3
COONa
2+
Cu
H
O
S
RCHN
HN
C
CH3
CH3
O
C
O
NHOCu
2. - -.
3. .
4. , , ( , . .).
5. - .
6. Na+, K+ .
, , , ( ).
. 1.
( 510 %).
2. :
) ;
) .
, ,

= 4,5 ( ):
425
O
S
H5C6CH2CHN
O
CH3
CH3
COOH
NaOH
O
S
H5C6H2CCHN
HN
C
CH3
CH3
COONa
O
ONa
C6H5CH2CONHCHC
COOH
HSC
CH3
CH3
H2NCHCOOH
3I
O
C6H5CH2CNHCHCOOH
COOH

HO3SC
CH3
CH3
H2NCHCOOH

I2 + 2Na2S2O389 Na2S4O6 + 2NaI

,
8 , = 1/8. .

, .
426
,%:
X =
V K T 100 C 100
5m
: V 0,01 ,
, ;
T
1 0,01 ;
0,01 ;

, , ;
m , ;
100/5 .
.
N- :
CH3
CH3
H
COO
H5C6H2CCHN
O
C2H5

,
, , = . .:
O
RCHN
O
S
N
CH3
CH3
+ NaOH 89
COONa
O
89
RCHN
HN
C
. NaOH
O
ONa
+ HCl 89 NaCl + H2O

427
CH3
CH3
COONa
3. .
. .
.
, , , , , . per os,
( ).
,

.
. -
, .
7- (7-) 7- (7-).
H2N
O
7
6
S1
CH2OCOCH3
COOH
4
7-
H2N
O
7
6
S1
2
3
CH3
COOH
4
7-
, - .
Cephalosporium salmosynnematum ,
.
- .
7- ,
., 7- , .

:
1. , ( ), ( ), , (, ).
2. , , .
3. , , , .
428
, - ,
.
:
R1HN
O
CH2R2
COOH
R1
R2
7-
Cefalexinum
CHC
*
()
Cefaloridinum
()
Cephazolin
HH2O
NH2 O
O
S
O
N
NCH2 C
N
N
Ceftriaxon
CH2C
CC
N
NOCH3
NH2
N
H3C
N
S
NaO
S
NCH3
S
7-
O
Cefalotinum
Cefapyrinum
CH2C
CH3C
S
O
N
SCH2C
CH3C
O
O`
O
O`
Cefuroxim
CC
NOCH3
NH2CO`
O
Ceftaxim
N
H2N
CC
S
NOCH3
* 4 COO.
429
CH3C
O
O`
. , . ( , ),
. .

.
. 1. - -.
2. -
(II) (III).
3. 80 %- 1 %- ,
-,
-.
. 1. ( ).
2. .
3. - (-, ).
. , .
.
, , .

. .

, , ; .

, - , :
O
CHCH2OH
O
COOH
N
3-(2-)-7--4--1-[3.2.0]-2-
- ,
.
:
, .
430
,
. .
1944
..
. Streptomyces griseus.
.
(Streptomycini sulfas)
O
CHO
H3C
HO
OH O
OH
OH
CH2OH
H3CNH
OH
3H2SO4
HO
H2NCNH
NHCNH2
NH
NH
N---L--L--

(1,3--2,4,5,6-) (N--L- L-).
. ,
, . . ,
, .
431

( N-) .
,
, N--L L-.
. 1. :
O
OH
O
CH3
(-----)
(III) , .
2.
- ,
- .
3.
:

();

( ).
. 1. .
2. , .
. , .
. , , , , .
. - , ,
(23 ).
-
,
, , , .
432
OR'
RO
OH
NH2
NH2
R, R' .
. - , ,
, .
, .
. 1. .
2. - ( ).
3.
(III) .
.
. 1. .
2. ( ).
3. .
. -
,
. , , ,
, .
-
- 1217
, ( ) .
, - , . 100 -
:
433
OR2 OR1
CH3 CH3
HO
O
H3C
O
O
H3C
CH2CH3
OH OH
CH3 CH3

(Erithromycini phosphas), , , .
. . ,
, .
-

, ,
-.
-
.
, , , , .
[3-(4--1-)-], ,
.
. -
. , . , - 0,30,45 .
.

, , . , .
, , , .
434
67 3540
.
:
, , , , , , , .
. , ,
, .
-
-
,
(, ).
, , .
. , .
. -
, ,
, , .

1940 .
, 1952- ,
.
,
, .
,
, :
();
();
-5,8- ().

, - .
. , ,
, .
1. . 1- . .: , 2001. 556 .
2. . 10- . .: ,
1968. 1079 .
3. . 11- . . I. .:
, 1987. 334 .
4. . 11- . . II. .:
, 1989. 398 .
5. / . . , . . , . . . .: - ; , 2001. 240 .
6. /
. . , . . . : , 1976. 248 .
7. /
. . . : ., 1984. 224
8. . . . .: , 1986.
768 .
9. . . .: 2. . 1: : . . - . . -. .:
. ., 1993. 432 .
10. . . : 2 . . 1: : . . - . . -.
, 1996. 608 .
11. . ., . . . .: , 1978. 256 .
12. . : 2 .: . .
.: , 1981; . 1. 616 .; . 2. 523 .
13. . ., . . . .
, . .: , 1989. 288 .
14. / .
. . . .: . ., 1989. 375 .
15. . : . . .: ,
1986. 584 .
16. . . : . :
2 . 13- . : , 1997. . 1. 560 .; . 2. 592 .
436
17. . . : 2 . .: ,
1976. . 1. 780 .; . 2. 827 .
18. / . . , . . , . . . : , 1984. 224 .
19. / . . , . . . : , 1978. 240 .
20. /
. . . , . . , .. , .. . .: , 1999. 896 .
21. . . .
: . ., 1985. 240
22. - ., . : . .
.: , 1981. 624 .
23. . ., . . - . .: , 1971. 328 .
24. / . . . . .: , 1987. 303 .
25. - / . . .
. . . : , 1989. 200 .
26. : . . /
. . . . . . : ,
1996. 777 .
27. . . : ., 1973. 495 .
28. British Pharmacopoeia, 1999. CD-ROM. Vol. 3.0.
29. European Pharmacopoeia. Third Edition. Supplement, 1998. Council
of Europe Strasbourg.
.................................................................................................................. 3

.......................................................................... 5
....................................................................... 5
.................................................................................. 5
.............................. 15
................................... 16
,
........................................................................................... 18
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............................................................................ 21
............................................................. 21
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................................................................................ 23
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................................................ 25
.......................................................................... 26
pH .......................................................................................................... 27
........................................................................ 28
...................................................................... 29
........................................................................... 29
.................................................................................................. 29
() .......................................... 30
() .................................................. 31
.................................... 32
..................................................................... 32
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438
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VI VII ......................................................... 39
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..................................................................................................... 44
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................................................................................................ 46
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5 %- ...................................................................... 47
10 %- .................................................................... 48
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.......................................... 50
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III, IV V ..................................................... 55
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10 %- ................................................................................ 57
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439

II ...................................................................... 66
, .................................................................. 66
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, ................................................................. 70
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, ..................................................................... 73
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I VIII ........................................................... 79
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, -32, ..................... 85
-, -131, ................. 86
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440

.................................................. 96
................................ 96
40 %- ....................................................................... 96
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- 10 %- ........................................... 119
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1 %- ..................................................................... 124
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-(-)- ................................................................ 132
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() ....................................................... 146
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441
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n- ................................................................................. 205
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() ............................................................................................ 208
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61145, , . , 26.

Farmaceutical Chemistry

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. . , . . , . .

.., .., ..,

+ 2H2O + Pb2+ 89 PbS5 + CH3COONH4 + 2H+

, (III) : NH4SCN, 4[Fe(CN)6],

5CaC2O4 + 2HCl 89 CaCl2 + H2C2O4

n = n0 + C1F1 + C2F2 ++CiFi ,

89 2CuOH5 + RCOONa + 4KNaC4H4O6 + 2H2O

+ Hg5 + 4KI + 2H2O

+ HOH89 R8COOH + R'OH

+ 2HCl 89 Cl26 + CaCl2 + H2O

(CH3COO)2Ca + (NH4)2C2O4 89 CaC2O45 + 2CH3COONH4

+ 2HCl + 2KI 89 I2 + 2KCl + CaCl2 + H2O

Na+ + Zn[(UO2)3(CH3COO)8] + CH3COO + 9H2O89

+ 2HCl 89 Cl2 + NaCl +

2Br + Cl2 89 Br2 + 2Cl

2H3O 89 2H2O + H26

K2Cr2O7 + H2SO4 89 H2Cr2O7 + K2SO4

H2N8 C 8NH8 C 8NH2

5Ag2SO3 + 5S + H2O 89 Ag2S5 + H2SO4

+ H2O 89 HNO3 + 2Bi

Bi2O3 + 3C 89 2Bi + 3CO6

2Bi2O35 + 2NO26 + 1/2O26 + H2O

Bi Na+ + Na+ + 2H+

Bi Na+ + H3Ind + Na+

NH3 + CO2 + H2O 89 NH4HCO3

893MgCO3Mg(OH)23H2O5 + 4Na2SO4 + 5CO26

2KAl(SO4)2 + 6NH4OH 89 2Al(OH)3 + K2SO4 + 3(NH4)2SO4

HCl + NaOH 89 NaCl + H2O

2MnO4 + 10SO42 + 16H+

5ZnO + 2CO26 + 3H2O

+ 3KOH 89 Hg5 + HCOOK + 2KCl + 2H2O

HgO + 2HCl 89HgCl2 + H2O

HgCl2 + Hg(CN)2 + H2O

53CuS + 8HNO3 89 3Cu(NO3)2 + 3S5 + 2NO6 + 4H2O

I2 + 2Na2S2O3 89 2NaI + Na2S4O6

AgNO3 + Cu(NO3)2 + NO6 + 2H2O

Cl2 + C2H5OH 89 CH3C

HCl + C2H5OH 89 C2H5Cl + H2O

2NaOH + Cl2 89 NaClO + NaCl + H2O

+ NaOH 89 CHCl3 + HCOONa

+ Hg5 + 4KI + 2H2O

3AgI5 + 3HNO3 + CO6

AgNO3 + NH4SCN 89 AgSCN5 + NH4NO3

2(C6H10O5)n + nH2O 88889 nC12H22O11 88889

+ 2MnHPO4 + K2HPO4 + 8H2O

89 2Ag5 + 2NH4NO3 + NH36 + CH3C

CH28 CH8 CH2

CHOH + 3(CH3CO)2O 89 CHOCOCH3 + 3CH3COOH

CHOCOCH3 + 3NaOH 89 CHOH + 3CH3COONa

HCOOH + NaOH 89 HCOONa + H O

NaOH + HCl 89 NaCl + H2O

NaOH + HCl 89 NaCl + H2O

+ 4NH3 89 (CH2)6N4 + 6H2O

2NH36 + Na2SO4 + 2H2O

NH2 I + 5KI + H2O

+ Hg5 + 4KI + 2H2O

+ 2NaOH 89 Na2SO4 + 2H2O

I2 + 2Na2S2O3 89 2NaI + Na2S4O6

+ CCl3COOH + HCl + H2O

Cl2 + 2NaOH + H26

NaOH + HCl 89 NaCl + H2O

+ 5CaSO45 + 10CO26 + 2K2SO4 + 4 MnSO4 + 16H2O

3[Kat]H+ + HOCCOONa 89 HOCCOOH + 3[Kat]Na+

HO`C`COOH + 3NaOH &' HO`C`COONa + 3H2O