Preparation and spectra of aminotetrazoles benzylated in the nucleus or in the side-chain

Abstract

Monobenzylation at the 1- and 2-positions and on the amino-group occurs when 5-aminotetrazole is treated with various para-substituted benzyl halides. The 1- and 2-benzyl derivatives predominate (30–40% each) and the benzylamino-isomer is a minor (10%) product. N.m.r. data were useful in locating the benzyl groups; the orientations were confirmed by i.r. and u.v. measurements, and by use of the thermal interconversion of the 5-amino-1-benzyl- and 5-benzylamino-tetrazoles.