Phosphorus oxychloride → 4-(Chloromethyl)-5-methyl-2-phenyl-1,3-oxazole

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Reaction Steps

383 g of phosphorous oxychloride was slowly added dropwise into chloroform (2 L) solution of 430 g of 4,5-dimethyl-2-phenyloxazole N-oxide. After the dropwise addition, the solution was stirred for 2 hours at room temperature. The reaction mixture was concentrated in vacuo, and 2 L of ethyl acetate was added to the residue. The foregoing ethyl acetate solution was added to mixed solution of 2 L of ice water and 1.2 L of 25% sodium hydroxide solution under stirring. The liquid was separated, and the ethyl acetate layer was washed with 1 L of brine, and dried with 300 g of anhydrous sodium sulfate. After filtration in vacuo, the filtrate was concentrated. Ethanol:n-hexane=1:10 (1.1 L) was added to the crystalline residue, and then filtered off. The crystal was dried under reduced pressure at 40° C. for 1 hour, 321 g of the subject compound was prepared.

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