Imidazole derivatives with potentially labile groups at the N-atom

A number of N-aminomerhyl and N-alkoxy(aroxy)methylbenzimidazoles are prepared. These compounds are decomposed in acid solution, giving benzimidazole. Sodamide reacts with them to give N-aminomethylbenzimidazole, and not the corresponding 2-amino derivative. The facility with which the compounds investigated decompose decreases in the order N-aminomethyl > N-aroxymethyl > N-alkoxymethylbenzimidazole. The mechanism of splitting is considered.