Tritylation of five-membered nitrogen heterocycles under conditions of phase-transfer catalysis

Treatment of imidazole, benzimidazole, benzotriazole, and 5-methyl- and 5-p henyltetrazoles with 4,4'-dimethoxytriphenyImethyl chloride in a two-phase system solid-liquid (sodium hydroxide-benzene in the presence of polyethyle ne glycol) smoothly yields the corresponding N-trityl derivatives. In the t wo-phase system methylene chloride-aqueous sodium hydroxide with tetrabutyl ammonium bromide as phase-transfer catalyst, N-trityl derivatives were obta ined only from 5-methyl- and 5-phenyltetrazoles.