Benzamide → 4-(Chloromethyl)-2-phenyl-1,3-oxazole

Participants

Reaction Conditions

Reaction Steps

A mixture of benzamide (0.8 g, 6.60 mmol) and 1,3-dichloropropan-2-one (1.00 g, 7.92 mmol) was heated at 130° C. stirring under nitrogen atmosphere for 1 hour (UPLC/MS complete conversion). The obtained brown solution was cooled to room temperature, and the brown solid was suspended in acetonitrile (25 ml) and heated to reflux. The white insoluble solid was eliminated by filtration, and the solution was allowed to cool to room temperature. The formed precipitate was collected by filtration and washed with acetonitrile (8 ml), dissolved in EtOAc (20 ml) and washed with aq. NaHCO3 (15 ml). The organic phase was dried (Na2SO4), filtered and evaporated to obtain 4-(chloromethyl)-2-phenyloxazole (315 mg, 24.7% yield).

Provenance & Evidence