Toluene → 2-Phenylthiomethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

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Reaction Steps

To a mixture of 4-isopropyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (7.0 g, 39.32 mmol) suspended in 150 ml of toluene was added phenylthiomethyl chloride (6.83 g, 43 mmol) and tetrabutylammonium bromide (1.26 g, 3.93 mmol). The resulting mixture was refluxed for 17 hours, cooled, filtered, and the filtrate was concentrated in vacuo. The residue was purified by column chromatography to afford 5.2 g of 2-phenylthiomethyl-4-isopropyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula VI: R1 =H; R2 =isopropyl; R3 =H).

Provenance & Evidence