Sulfuryl chloride → 2-Chloromethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

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Reaction Steps

To a solution of 2-phenylthiomethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (5.23 g, 17.43 mmol) in 200 ml of methylene chloride was added sulfuryl chloride (2.15 ml, 26.07 mmol) and the mixture was stirred for 3 hours at room temperature. The mixture was concentrated in vacuo, the residue triturated in hexane (200ml) for 2 hours, and the resulting solid was filtered and dried to afford 3.54 g (90%) of 2-chloromethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula II: R1 =H; R2 =propyl; R3 =H; X=Cl) as a solid.

Provenance & Evidence