Reaction of Alkylphenols with Cyanuric Chloride-N, N-Dimethylformamide Adduct

Abstract

The reaction of alkylphenols(2)with cyanuric chloride-DMF adduct has been investigated. When the reactions were carried out at 30-40°C, where cyanuric chloride reacts with DMF to give 1 : 2 adduct, the corresponding formates of (2)were obtained. On the other hand, at 60-70°C, N²-(alkylphenoxycarbony1)-N¹, N¹-dimethylformamidines(3)were obtained. The hydrolyses of(3)in dilute acidic ethanol gave N-formylcarbamates (5)or carbamates(6). Reductions of(3)with NaBH₄ in methanol afforded dimethylaminomethylcarbamates(7).