Phosphorus oxychloride → HCID 9946483, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4-methylsulfonyl-benzoic acid (2.5 mmol, 500 mg), 2-methylthiosemicarbazide (5a) (2.5 mmol, 468 mg) in anhydrous dioxane (5 mL) at 65° C., POCl3 (3 mmol, 280 μL) was added, and the mixture was warmed at 95° C. for 5 hours. The solvent was removed by distillation under reduced pressure to give a crude material which was basified at pH 8-7 with a saturated solution of NaHCO3. The aqueous phase was extracted with dichloromethane. The organic layer was washed with saturated solution of NaCl, dried over magnesium sulfate, filtered, and distilled to give a residue which was purified by silica gel chromatography (eluted with a gradient of cyclohexane/ethyl acetate finishing with the ratio 80:20) to afford 230 mg of the title compound. Yield: 26%.

Provenance & Evidence