Methyl oxo[(phenylmethanesulfonyl)amino]acetate → 3(2H)-Isothiazolone, 4-hydroxy-5-phenyl-, 1,1-dioxide

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Reaction Conditions

Reaction Steps

To a solution of methyl N-benzylsulfonyloxamate (2.0 g., 0.077 mol) in dimethyl formamide (15 ml.) was added in portions potassium tert-butoxide (1.74 g., 0.016 md). After stirring overnight, the solids were removed by filtration and washed with ether. The filtrate was evaporated to dryness. The solid residue, combined with the first fraction, was dissolved in a small volume of water. The aqueous solution was made strongly acidic by the addition of concentrated hydrochloric acid. After cooling at 0° C. for one hour, there was obtained on filtration the title compound (0.51 g.) m.p. 240°-251° C. (dec.). Anal. Calc'd. for C9H7NO4S: % C, 48.00; % H, 3.13; % N, 6.22. Found: % C, 48.00; % H, 3.12; % N, 6.45. When 4-chlorobenzylsulfonamide is employed as the starting material in Example 1 in place of benzylsulfonamide, and the procedures of Steps A and B are followed, there is obtained 5-(4-chlorophenyl)-4-hydroxy-3(2H)-isothiazolone-1,1-dioxide. Similarly, when 4-methylbenzylsulfonamide is employed as the starting material in Example 1, there is obtained 4-hydroxy-5-(4-methylphenyl)-3(2H)-isothiazolone-1,1-dioxide. When 3,4-dichlorobenzylsulfonamide is employed as the starting material in Example 1, there is obtained 5-(3,4-dichlorophenyl)-4-hydroxy-3(2H)-isothiazolone-1,1-dioxide. And when 3,5-diethylbenzylsulfonamide is employed as the starting material in Example 1, there is obtained 5-(3,5-diethylphenyl)-4-hydroxy-3(2H)-isothiazolone-1,1-dioxide.

Provenance & Evidence