The chlorination of some N,N-Dimethylanilines with 1,3,5-Trichloro-1,3,5-triazine-2,4,6(1H,3H,5H)-trione (Trichloroisocyanuric acid)

Abstract

The reaction of some representative N,N-dimethylanilines and of Fischer's base (1,3,3-trimethyl-2-methyleneindoline) with trichloroisocyanuric acid in concentrated sulfuric acid has been investigated. In many cases mixtures of chlorinated products were obtained; these mixtures were examined both by gas-liquid chromatography and by proton magnetic resonance spectroscopy. The reaction of N,N-dimethylaniline with dichloroisocyanuric acid was also studied.    

A feature of these chlorinations is the marked tendency for substitution to occur ortho to the dimethylamino group. This behaviour therefore differs from that reported for the corresponding brominations involving dibromoisocyanuric acid, where meta-substitution was observed.