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

HRID 2296338Notes

Reaction equation

HRID 2296338 reaction equation
[CH2:1]([S:8]([NH:11][C:12](=[O:17])[C:13](OC)=[O:14])(=[O:10])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+]>CN(C)C=O>[OH:14][C:13]1[C:12](=[O:17])[NH:11][S:8](=[O:10])(=[O:9])[C:1]=1[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 13186355Methyl oxo[(phenylmethanesulfonyl)amino]acetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 6855393(2H)-Isothiazolone, 4-hydroxy-5-phenyl-, 1,1-dioxideYield 2.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  1. customthe solids were removed by filtration
  2. washwashed with ether
  3. customThe filtrate was evaporated to dryness
  4. dissolutionwas dissolved in a small volume of water
  5. additionThe aqueous solution was made strongly acidic by the addition of concentrated hydrochloric acid

Sources & evidence

ORD record
ord-d7dbc6b2c5dd4f2d93bc948ab8682c5b
Source dataset
uspto-grants-1984_01
Patent number
US04428956

Reaction notes

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