Aminolysis of 1,2,3‐benzotriazin‐4(3H)‐thione

Abstract

AbstractA series of 4‐N‐substituted 1,2,3‐benzotriazin‐4(3H)‐imines was prepared by aminolysis of 1,2,3‐benzotriazine‐4(3H)‐thione and its 6‐chloro derivative with primary aliphatic amines. The reaction was shown to be sensitive to amine structure and to reaction conditions. Frequently observed tar formation is attributed to instability resulting from the cryptodiazonium character of the triazine ring. Spectral data substantiate the thiono and imino structures of the starting compounds and products, respectively, in the solid state.