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

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A mixture of benzamide (0.80 g, 6.60 mmol) and 1,3-dichloropropan-2-one (1.01 g, 7.92 mmol) was heated to 130° C. for 1 hour under nitrogen atmosphere. The crude was purified by crystallization from acetonitrile (25 ml): the suspension was heated to reflux and a brown solution with a white insoluble solid was obtained. It was filtered and the solution was cooled to room temperature. A precipitate formed and the suspension was filtered on a buckner funnel washing with acetonitrile (8 ml). The solid was recovered from the filter, dissolved in EtOAc (20 ml) and washed with 1N NaHCO3 (15 ml). The organic phase was dried (Na2SO4) and evaporated to give 4-(chloromethyl)-2-phenyloxazole (315 mg, 25% yield) as a pale brown solid.

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