Sulfuryl chloride → 2-chloromethyl-tetrahydropyrrolo[1,2-b]-1,2,5-thiadiazol-3 (2H)-one 1,1-dioxide

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Reaction Steps

To a solution of 2-phenylthiomethyltetrahydropyrrolo[1,2-b]-1,2,5-thiadiazol-3 (2H) -one 1,1-dioxide (5 g) in 130 ml of methylene chloride was added sulfuryl chloride (2.02 ml) and the mixture was stirred for 2 hours at room temperature. The mixture was concentrated in vacuo, the residue triturated in hexane (2×, 150 ml, 75 ml) with stirring, the solvent decanted, and the resulting solid filtered and dried to afford 2.96 g (92%) of 2-chloromethyl-tetrahydropyrrolo [1,2-b]-1,2,5-thiadiazol-3 (2H) -one 1,1-dioxide (Formula II: X'=Cl; R1 =H; R2 and R3 together=--(CH2)3 --)as a solid, m.p. 46.5°-47.5° C.

Provenance & Evidence