Chloromethyl phenyl sulphide → 2-Phenylthiomethyl-4-propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

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Reaction Steps

A mixture of 4-propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (9 g), phenylthiomethyl chloride (7.43 g) and tetrabutylammonium bromide (1 g) suspended in 200 ml of toluene was refluxed for 8 hours, cooled, and concentrated in vacuo. The residue was purified by flash chromatography (15%-20% ethyl acetate in hexane) to afford 8.5 g (88%) of 2-phenylthiomethyl-4-propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula VI: R1 =H; R2 =propyl; R3 =methyl).

Provenance & Evidence