Cesium carbonate → HCID 19424441, compound

Participants

Reaction Steps

To a mixture of 4-phenylmethyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide cesium salt (prepared by reacting 11.43 g (50.52 mmol) of the dioxide in methanol with 8.23 g (25.26 mmol) of Cs2CO3 followed by removal of the solvent) in 150 ml of DMF was added in one portion phenylthiomethyl chloride (8.82 g, 55.57 mmol) and the mixture was heated at 80°-90° C. under nitrogen for 17 hours. The mixture was cooled and poured into 600 ml of ice/water. The reaction mixture was extracted with ethyl acetate (3x), the organic layer was dried over sodium sulfate, and concentrated in vacuo. The residual yellow oil was purified by silica column chromatography (5%-10% ethyl acetate in hexane) to afford 16.88 g (95.9%) of 2-phenylthiomethyl-4-phenylmethyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula VI: R1 =H; R2 =CH2Ph; R3 =H) as an yellow oil.

Provenance & Evidence