Reactions of Alkyl Isocyanates and Chlorosulfonyl Isocyanate with 1H-Tetrazol-5-amine and Conversion of Reaction Products to (1H-Tetrazol-5-yl)ureas

Article abstract of DOI:10.1021/jo01297a026

5-Amino-N-alkyl-1H-tetrazole-1-carboxamides 2-6 were prepared by reaction of alkyl isocyanates with 1H-tetrazol-5-amine (1) and thermally isomerized to (1H-tetrazol-5-yl)ureas 7-11.The parent compound of the former series, 5-amino-1H-tetrazole-1-carboxamide (12), was prepared by treatment of 1 with aqueous isocyanic acid, and the parent compound of the latter series, (1H-tetrazol-5-yl)urea (13), was prepared either by heating 12 or by hydrolysis of 5-azido-2H-1,2,4,6-thiatriazin-3(4H)-one 1,1-dioxide (14).X-ray crystallographic studies were used to establish the structures of the octyl derivative 4 and the thiatriazine 14.