Some nucleophilic reactions of cyanuric chloride and of certain 2,4-dichloro-1,3,5-triazines with compounds containing reactive hydrogen

Abstract

Cyanuric chloride and 2,4-dichloro-1,3,5-triazines react with carbohydrazides, diarylguanidines, phthalimides, arylsulphonamides, and isopropylidene arylsulphonohydrazides in well-defined, stepwise manner as with amines, but with several other types of reactive compound, demarcation of the successive stages of replacement is less clear, and substantially homogeneous products are obtained only in specific instances and under narrow ranges of conditions. Such reactive compounds include alcohols, phenols, aliphatic, aromatic, and heterocyclic thiols, alkyl dithiocarbamates, alkyl xanthates, and alkyl trithiocarbonates. Details are given for preparing new monochloro- and dichloro-triazines bearing a variety of substituent groups linked through nitrogen, oxygen, or sulphur.