Reactions of aniline in acetic acid solutions containing cyanuric chloride and hydrogen chloride acceptors

Abstract

Two reaction pathways in acetic acid solution containing cyanuric chloride, aniline, and some hydrogen chloride acceptors (triethylamine, sodium acetate, pyridine) were studied. Both aryl amination and acylation can be performed with high yields under proper reaction conditions. Contrary to the only known literature report on the reactions between carbonic acids and cyanuric chloride in the presence of a hydrogen chloride acceptor (triethylamine), it was established that acid chlorides are not formed. A scheme involving the replacement of chlorine atoms by acetate ion in the initial stage was proposed for the acylation of aniline promoted by cyanuric chloride.Key words: acetic acid, acylation, aniline, cyanuric chloride, aryl amination.