Methanesulfonic Acid → Methanesulfonic acid, 1H-benzotriazol-1-yl ester

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Reaction Steps

In dichloromethane (20 ml) are added 1-hydroxy-1,2,3-benzotriazole (2.70 g) and methanesulfonic acid (1.92 g) and thereto is added triethylamine (5.6 ml). To the solution is added dropwise thionyl chloride (1.43 ml) with stirring under ice-cooling during 15 minutes. The mixture is stirred at the same temperature for 1 hour and 10 minutes and at room temperature for 7 hours and 45 minutes, and then allowed to stand overnight. Dichloromethane is distilled off under a reduced pressure. To the residue are added water (30 ml) and ethyl acetate (100 ml). The ethyl acetate layer is washed with a saturated aqueous sodium hydrogen carbonate and water in order and dried over anhydrous sodium sulfate. After drying, the solvent is distilled off. To the residue is added petroleum ether and the mixture is filtered to give 1-methanesulfonyloxy-1,2,3-benzotriazole (1.2 g).

Provenance & Evidence