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Paper | Regular issue | Vol 48, No. 10, 1998, pp.2111-2123
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8271
The Formaiton of 3-Chloro-1,2,5-thiadiazoles from α-Oximidonitriles. Optimizaiton and Mechanistic Insights

John M. McGill* and Marybeth S. Miller

*Chemical Process Development, Tippecanoe Laboratories, Eli Lilly & Company, Lilly Corporate Center, Lafayette, Indiana 47902, U.S.A.


The optimized formation of substituted 3-chloro-1,2,5-thiadiazoles (2) and (3) from the α-oximidonitrile (4) is described. New mechanistic insight into the formation of 3-chloro-1,2,5-thiadiazoles comes from the identification of a reaction intermediate in the thiadiazole ring-forming reaction.