Cytotoxic compounds. Part 22. Reactions of 2,2′-iminodiethanol with some chloronitrobenzenes

Abstract

Conditions have been established for the reaction of 2,2′-iminodiethanol with 2,3-, 2,4-, and 2,5-dichloronitrobenzene to give, as major products, the 2-(bis-2-hydroxyethylamino)-compounds; 3,4-dichloronitrobenzene and 4-chloro-3-nitrobenzoic acid gave the 4-(bis-2-hydroxyethylamino)-compounds. Minor products were the corresponding 2-hydroxyethylamino-compounds and the amino- or azo-compounds formed by reduction of the nitro-group.

Conversion of the bis-2-hydroxyethylamino-compounds into the bis-2-chloroethylamino-derivatives, followed by catalytic hydrogenation of the nitro-group and reaction of the resultant primary amines with aryl chloroformates, led to mustard carbamates of potential interest as anti-tumour agents.