Thiophenol → HCID 67544690, compound

Participants

Reaction Steps

To a suspension of 0.76 g (4.8 mmol) of N-phenyl-1-propynecarboxamide in toluene (15 mL) was added 1.0 g (4.8 mmol) of phosphorus pentachloride at room temperature and stirred for 4 hours. After removal of the solvent, the residue was dissolved in DMF (15 mL). To a solution of 1.2 mL (12 mmol) of thiophenol in DMF (15 mL) was added 0.31 g (7.1 mmol) of sodium hydride (60% in oil) under ice cooling and stirred for 0.5 hours. The mixture was added to the above-described DMF solution of the residue and stirred under ice cooling for 3 hours. After dilution with tert-butyl methyl ether (150 mL), the mixture was washed sequentially with water and a saturated NaCl solution, dried over anhydrous MgSO4, and concentrated under vacuum. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1) to obtain 0.39 g of phenyl N-phenyl-3-(phenylthio)-2-butenimidothioate (hereinafter referred to as the present compound 44).

Provenance & Evidence