4-Chlorobenzoyl chloride → 4-Chloro-N-(3-[1,3]dioxolan-2-yl-phenyl)-benzamide

Participants

Reaction Steps

A solution of 3-aminobenzaldehyde ethylene acetal (10 g, 60.5 mmol) and TEA (7.35 g, 72.6 mmol) in ethyl acetate (100 mL) at 0° C. is treated dropwise with 4-chlorobenzoyl chloride (9.44 mL, 72.6 mmol) during 30 min. The reaction mixture is stirred at RT for 3 h before dilution with EtOAc. The medium is washed twice with sat. aq. NaHCO3 (100 mL) and once with brine (100 mL). The organic layer is dried over MgSO4, filtered and evaporated. The residual oil is triturated with ethyl acetate and the resulting crystalline material is filtered to give the title compound (14.33 g, 78%) as a slightly pink solid; LC-MS B: tR=0.86 min; [M+H]+=304.03.

Provenance & Evidence