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Note | Regular issue | Vol 53, No. 3, 2000, pp.729-732
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8804
Efficient Route to 1-Dimethylsulfamoyl-4-iodoimidazole, Isomerisation of 1-Dimethylsulfamoyl-5-iodoimidazole to 1-Dimethylsulfamoyl-4-iodoimidazole

Lakshmi Bhagavatula, Ramiya H. Premchandran,* Daniel J. Plata, Steven A. King, and Howard E. Morton

*PPD Process Research, D45N. Bldg. R8, Abbott Laboratories, N. Chicago, IL60064, U.S.A.

Abstract

An efficient method has been developed for regioselective protection of 4-iodoimidazole using N,N-dimethylsulfamoyl chloride and 50% aqueous NaOH in THF leading to N,N-dimethylsulfamoyl-4-iodoimidazole(1) in 97% yield and >98% purity. The rearrangement of by-product 5-iodosulfonamide (2) to the desired product (1) is a key feature of this procedure.