Water → N,N-Dimethyl-3-amino-6-chloro-2-hydroxybenzenesulfonamide

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Reaction Steps

11 ml (205 mmol; 1.20 V) of sulfuric acid and 11 ml of water were added dropwise to a solution of 9.12 g (28.8 mmol; 1.0 eq) of 2-tert-butyl-6-chlorobenzooxazole-7-sulfonic acid dimethylamide in 41 ml of 1,4-dioxane. The reaction medium was refluxed for six and a half hours. The reaction medium was concentrated and 440 ml of 1 N sodium hydroxide were added (pH at 8). The solution was extracted with ethyl acetate. The organic phases were combined, dried over magnesium sulfate, filtered and evaporated. 6.94 g of 3-amino-6-chloro-2-hydroxy-N,N-dimethylbenzenesulfonamide were obtained in the form of a brown solid. Yield=96%.

Provenance & Evidence