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 (1.1 g, 3.6 mmol) in 10 ml of methylene chloride was added sulfuryl chloride (0.44 ml, 5.5 mmol) and the mixture was stirred for 3 hours at room temperature. The mixture was concentrated in vacuo, the residue triturated in hexane (50ml) for 1 hour, the resulting solid filtered and purified by silica gel flash column chromatography (20-25% of ethyl acetate in hexane) to afford 0.31 g 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, m.p. 62°-63.5° C.

Provenance & Evidence