关键词:

亚氨基芪, 氯甲酰化, 保护基, 脱保护

Abstract:

A novel synthesis process of 5H-dibenz［b,f］azepine was studied.It is an important intermediate of 5H-dibenz［b,f］azepine-5-carboxamide, used in genetic engineering, materials science and so on.With 10,11-dihydro-5H-dibenz［b,f］azepine as raw material, 5-chloroformyl-5H-dibenz［b,f］azepine was prepared by reflux with triphosgene in toluene, brominated with bromine in chlorobenzene, and dehydrobrominated at 130℃, finally, the title compound was obtained by removing chloroformyl group with NaOH in isopropanol with 80.4% overall yield.The optimal reaction conditions and yields (temperature, time, molar yield) were as follows: acyl chlorination, 110℃, 10 h, 93.0%;bromination, dehydrobromination, 100℃, 2 h, 130℃, 5 h, 88.0%;removal of chloroformyl group, 40℃, 3 h, 98.2%. The melting point of the title compound was the same as literature reported, and its structure was confirmed by ¹H NMR.The optimal technology condition to remove chloroformyl group as protection group and its application of protection for some amine compounds were also studied.

Key words:

亚氨基芪, 氯甲酰化, 保护基, 脱保护