Preparation of halomethyl??1, 3, 4??thiadiazoles. Conversion to 2??amino??5??(1??methyl??5??nitro??2??imidazolyl)??1, 3, 4??thiadiazole, an important antimicrobial agent

WA Remers, GJ Gibs, MJ Weiss

Index: Remers,W.A. et al. Journal of Heterocyclic Chemistry, 1969 , vol. 6, p. 835 - 840

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Citation Number: 18

Abstract

Abstract A new route for the synthesis of 2-amino-5-(l-methyl-5-nitro-2-imidazolyl)-1, 3, 4- thiadiazole (1) is described. This route was based upon the preparation of 2-amino-5- halomethyl-1, 3, 4-thiadiazoles by condensation of haloacetic acids with thiosemicarbazide. One of these intermediates, 2-acetamido-5-dichloromethyl-1, 3, 4-thiadiazole (4), was hydrolyzed to the corresponding 5-amino-2-carboxaldehyde 6, which was trapped as its ...