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

Participants

Reaction Conditions

Reaction Steps

1-Hydroxy-1,2,3-benzotriazole (648 g) and triethylamine (675 ml) are dissolved in benzene (2,800 ml). To the solution is added dropwise a solution of methanesulfonyl chloride (535 g) in benzene (675 ml) with stirring at a temperature of lower than 10° C. over a period of 2.2 hours. The mixture is stirred at the same temperature for 2.3 hours and allowed to stand overnight. To the reaction mixture is added water (1,000 ml). The benzene layer is separated out. The aqueous layer is extracted twice with ethyl acetate (3,000 ml and 2,000 ml), and the extracts are combined and washed with a saturated aqueous sodium hydrogen carbonate (200 ml×2) and water and dried over anhydrous magnesium sulfate. After drying, the solvent is distilled off under a reduced pressure. The resulting crystals are washed with petroleum ether (500 ml) and dried to give faint yellow crystals of 1-methane-sulfonyloxy-1,2,3-benzotriazole (842 g), melting point: 88°-90° C.

Provenance & Evidence