Phosphorus oxychloride → HCID 18172446, compound

Participants

Reaction Steps

A solution of 4-benzyloxy-N-phenethylbenzamide (1.000 g, 3.0 mmol) in POCl3 (10 ml, 107.3 mmol) was refluxed under N2 for 18 hr, then the cooled reaction mixture was slowly added to ice-water (50 ml) with stirring. The resulting mixture was extracted with EtOAc (4×20 ml), then the remaining aqueous layer was basified to pH 10 with concentrated ammonia (80 ml). This was extracted with EtOAc (3×50 ml), then the combined extracts were dried over MgSO4 and concentrated in vacuo to give 0.270 g of yellow solid. Purification by flash chromatography, eluting with hexane:EtOAc (6:4) gave 0.151 g (16% yield) of yellow solid.

Provenance & Evidence