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

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4-propyl-1,2,5-thiadiazolidin-3-one 1,1dioxide (1.0 g, 5.6 mmol) suspended in 15 ml of toluene containing tetrabutylammonium bromide (0.18 g, 0.56 mmol) was added phenylthiomethyl chloride (0.98 g, 6.2 mmol) and the resulting mixture was refluxed (120° C.) for 20 hours. The mixture was cooled, filtered, and the filtrate was concentrated in vacuo. The residue was purified by silica gel flash column chromatography (20% of ethyl acetate in hexane) to afford 1.16 g of 2-phenylthiomethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula VI: R1 =H; R2 =propyl; R3 =H).

Provenance & Evidence