'larnides also
pror.rv-acetylaniiine
rone in g0?o yietd
Reacrions of
Aqdamtnes lOAl
OH
",*{}$_L<l
L-,/ l1 No
Sulfatbiazole
NH,
)'.
V
-'o
26.4
26.5
robenzophenone
$O.qa)
(a) N,N-Dimethylaniline
(c) m-Chloroaniline
(b) p-Chloroaniline
-2,a_limethylaniiine
(d)
of amino-sub_
rne that allow_.
rofthousand_.
'osulfonation
zenesulfonvl
nide, Hydro_
drolysis can
euse suifon-
/->(*''
(/
HNo, + Hzso4
,4'---.rirz*
Hso4- + 2H2o
(/"
Alkylamines also react with nitrous acid., but the products of these reactions,
alkanediazonium salts, are too reactive to isolaL since they lose
nitrogen
instantly to yield carbocations.
NH"
t"
:?:o
N&
fouilamide
tulfa drugr
ne.
* 'r
H2Soa
[n
. -HSo4]
__--., R* -HSo4 +
.r'',-u;u-'*
(}"
HSon-
:Nu-
0*"
N2
\ "'-"' ""-'''="""
1008
CHAPTER
26
*n=,,,,-J
polar, one.
,4-'-zB'
(/
(\'
\-/
C=N
,4-"-/cl
(/+
,Z-\1oH
,4t--r'H
U
Figure
26.3
*.-cr*'' #
1,,",(rn=NHSo4-
H,C
p-Bromotoluene
p-Methylaniline
Cr"" #
*
]
l er-=NHSoa'
-'- er'
Iodobenzene
(677o)
,ffi
iffi
26,g
Reactions of
Arytamines
I OO9
ffij
Y=N
CH,
Hso4-
C=N
COOH
o_Methylbenzonitrile
o-Methyltrenzoic
CH,
HNO,
KCN
H2SOl
,,-Methylaniline
CUCN
o-Methylbenzenediazonium bisulfate
acid
NI{"
OH
2',
\A*o,
-t
Hso' (' \
HNO,
H2SOI
NO,
7x-f{if,1'6*nilins
Vwo,
m.Nitrophenol
(86Va)
CHB
p.Methytaniline
l:
-lll
2Brz.'"$"'
Br
Y=N Eso4Br
}INO,
II3PO2
H2SOI
CHs
CH,
CH,
3,5-Dibromotoluene