Thionyl Chloride → 6-(4-Chlorobutoxy)-1,4-dihydro-2H-3,1-benzoxazin-2-one

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Reaction Steps

Sixty grams (0.253 mol) of 6-(4-hydroxy-butoxy)-4H-3,1-benzoxazin-2-one and 5 ml of pyridine are added to 300 ml of thionyl chloride, under stirring, at ambient temperature. After refluxing for two hours, the excess thionyl chloride is distilled off in a rotary evaporator, and the residue is taken up in chloroform and is stirred with the same volume of ice water for 30 minutes. Then, the chloroform phase is removed, washed twice with water, and dried with sodium sulfate, and the chloroform is distilled off. The residue is recrystallized from toluene/diisopropylether (3:1).

Provenance & Evidence