The condensation of aromatic nitriles with 4-aminoazobenzene by AlCl
3 gave the following amidines having azo group N- (4-phenylazo) phenylbenzamidine (1a), N- (4-phenylazo) phenyl-
m-toluamidine (1b), N- (4-phenylazo) phenyl-
p-toluamidine (1c),
p-chloro-N- (4-phenylazo) phenylbenzamidine (1d) and N- (4-phenylazo) phenyl-2-naphthamidine (1e).
ArC=NH-NH-_??_-N=N-_??_ Ar=C
6H
5 (1a),
m-CH
3C
6H
4 (1b),
p-CH
3C
6H
4 (1c),
p-ClC
6H
4 (1d), 2-C
10H
7 (1e)
The HCl-adducts of the above amidines were converted into the corresponding 2-aryl-5-phenylazobenzimidazole [(2a), (2b), (2c) and (2d)] by N'-chlorination by sodium hypochlorite and the subsequent dehydrochlorination by NaHCO
3.
ArC=N-NH-_??_-N=N-_??_ Ar=C
6H
5 (2a),
m-CH
3C
6H
4 (2b),
p-CH
3C
6H
4 (2c),
p-ClC
6H
4 (2d)
Upon treatment with N, N-dimethylformamide dimethylacetal, the above amidines gave the corresponding N-dimethylaminomethylidene-N'- (4-phenylazo) phenylamidine [(3a), (3b), (3c), (3d) and (3e)].
ArC-N=CHN (CH
3)
2=N-_??_-N=N-_??_ Ar=C
6H
5 (3a),
m-CH
3C
6H
4 (3b),
p-CH
3C
6H
4 (3c),
p-ClC
6H
4 (3d), 2-C
10H
7 (3e)
The corresponding N'- (4'-phenylazo) benzoyl-N- (4-phenylazo) -phenylamidine [(4a), (4b), (4d) and (4e)] were also obtained by the condensation of p-phenylazobenzoyl chloride with the aid of NaHCO
3.
ArC=NCO-_??_-N=N-_??_-NH-_??_-N=N-_??_ Ar=C
6H
5 (4a),
m-CH
3C
6H
4 (4b),
p-ClC
6H
4 (4d), 2-C
10H
7 (4e)
(1a), (1b), (1c), (2a), (2b), (2c), (3a), (3b), (3c), (4b) and (4d) dyed acetate fiber yellow or light yellow.
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