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Report | Regular issue | Vol 16, No. 9, 1981, pp.1561-1564
Published online, 1st January, 1970
DOI: 10.3987/R-1981-09-1561
1,2,5-Thiadiazole-1-oxides. I. Synthesis and Reactions of Alkoxy and Alkylthio Analogs

Sandor Karady,* Joseph S. Amato, Daniel Dortmund, and Leonard M. Weinstock

*Division of Merec and Co., Inc, Merck Sharp and Dohme Research Laboratories, Rahway, New Jersey 07065, U.S.A.

Abstract

Diethoxy and dithiomethyl 1,2,5-thiadiazole oxides were synthesized from the corresponding oxalimidates with thionyl chlorides. The alkoxy and alkythio groups were readily replaced by amines, carbon nucleophiles and hydroxide. The resulting hydroxy compounds were alkylated and acylated on the ring nitrogen. The N-alkyl products could be also obtained by thermal O to N rearrangement of the alkoxy derivatives.