Reactions of NN-Diphenylcarbamoyl chloride III. As an acylating agent in the Friedel-crafts reaction

Abstract

The reaction of NN-diphenylcarbamoyl chloride with aromatic compounds under Friedel-Crafts conditions to give aromatic acid NN-diphenylamides has been studied. Chlorinated hydrocarbon solvents, especially ethylene dichloride, were the most useful reaction media. Acylation of naphthalene occurred predominantly at the 1-position. Mesitylene, durene, and pentamethylbenzene were readily acylated but not fluoro- or chloro-benzene. With the exception of the sterically hindered amides obtained from mesitylene, durene, and pentamethyl-benzene, the resultant diphenylamides were readily hydrolysed by alkali to the parent aromatic acids.