Diethyl Ether → 1-(p-Chlorobenzenesulfonyloxy)-6-chloro-1,2,3-benzotriazole

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Reaction Steps

In 1 N aqueous sodium hydroxide (300 ml) is dissolved 1-hydroxy-6-chloro-1,2,3-benzotriazole (38 g) and thereto is added ether (100 ml). To the solution is added dropwise p-chlorobenzenesulfonyl chloride (57 g) with stirring under ice-cooling during 15 minutes, and the mixture is stirred at the same temperature for 70 minutes. The reaction mixture is extracted with ethyl acetate. The extract is washed with a saturated aqueous sodium hydrogen carbonate and water in order and dried over anhydrous magnesium sulfate. After drying, the solvent is distilled off, and the resulting crystals are recrystallized from benzene-petroleum ether to give 1-(p-chlorobenzenesulfonyloxy)-6-chloro-1,2,3-benzotriazole (70.5 g), melting point: 125°-127° C. Infrared spectrum (Nujor): 1190, 1085 cm-1.

Provenance & Evidence