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

참여 물질

반응 단계

3.4 ml of sulfuric acid (63.59 mmol; 1.16 V) and 3.4 ml of water were added to a solution of 2.93 g of 2-tert-butyl-6-chlorobenzooxazole-7-sulfonic acid dimethylamide (9.25 mmol; 1.0 eq) in 13 ml of 1,4-dioxane. The reaction medium was refluxed for four and a half hours. The reaction medium was concentrated. 130 ml of 1 M sodium hydroxide were added to the residue (pH=10), followed by 400 ml of water. The solution was extracted with ethyl acetate (2×250 ml). The organic phases were combined, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was chromatographed on silica gel (250 g prepacked column: eluent heptane/ethyl acetate, from 20% to 40% of ethyl acetate, flow rate 100 ml/min). 1.66 g of 3-amino-6-chloro-2-hydroxy-N,N-dimethylbenzenesulfonamide were obtained. Yield=72%.

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