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Paper | Special issue | Vol 37, No. 2, 1994, pp.793-805
Published online, 1st January, 1970
DOI: 10.3987/COM-93-S55
Preparation of New Thiohydroxamic Acid Derivatives: Synthesis of Substituted 1-Hydroxy-1,2-dihydoroimidazole-2-thiones

Derek H. R. Barton, Ching-Yu Chern, and Catherine Tachdjan*

*Department of Chemistry, Texas A & M University, College Station, Texas 77843-3255, U.S.A

Abstract

A general method for the synthesis of the title compounds is reported. The N-phenacylarylamines (11), prepared from the corresponding phenacyl bromides (9) and arylamines (10), give the thiono (or dithio) carbamates (12) on treatment with phenoxythionocarbonyl or thiophenoxythionocarbonyl chlorides and potassium carbonate in dichloromethane. The desired thiohydroxamic acids (13) are obtained by heating compounds (12) with hydroxylamine hydrochloride in pyridine/ethanol.