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

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Reaction Steps

To a mixture of 4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (5.1 g, 28.65 mmol) suspended in 210 ml of toluene was added tetrabutylammonium bromide (0.92 g, 2.86 mmol) and phenylthiomethyl chloride (4.93 g, 2.86 mmol) and the resulting mixture was refluxed for 18 hours. The mixture was cooled, filtered, and the filtrate was concentrated in vacuo. The residue was purified by silica gel flash column chromatography (20% ethyl acetate in hexane) to afford 5.39 g (63%) of 2-phenylthiomethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula VI: R1 =H; R2 =propyl; R3 =H).

Provenance & Evidence