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-phenylthiomethyl-tetrahydropyrrolo[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 (2x, 150 ml, 75 ml) with stirring, the solvent decanted, and the resulting solid filtered and dried to afford 2.96 g (92%) of 2-chloromethyltetrahydropyrrolo[1,2-b]-1,2,5-thiadiazol-3(2H)-one 1,1-dioxide (Formula II: R1 =H; R2 and R3 together =-(CH2)3 -; X'=Cl) as a solid, m.p. 46.5°-47.5° C.

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