Formation of N-substituted trichloroacetamides from amines and hexachloroacetone

Abstract

Procedures are described for converting primary amines into their well-crystalline trichloroacetyl-derivatives by treatment with hexachloroacetone under mild conditions. Although secondary aromatic N-methylamines are unaffected by hexachloroacetone, saturated heterocyclic amines react vigorously.

A mechanistic study using 2-amino-4-t-butylthiazole showed that the reaction is first order in hexachloroacetone, second order in amine, and base-catalysed; there is no appreciable kinetic isotope (H/D) effect nor accumulation of intermediates during the reaction. A sequence which accommodates these results is suggested.