1,2-Benzisothiazole-2(3H)-acetamide, N-(5-methyl-3-isoxazolyl)-3-oxo-, 1,1-dioxide → Methyl 2-{[({[(5-methyl-3-isoxazolyl)amino]carbonyl}methyl)amino]sulfonyl}benzoate
Reaction equation
[CH3:1][O-:2].[Na+].[CH3:4][C:5]1[O:9][N:8]=[C:7]([NH:10][C:11](=[O:25])[CH2:12][N:13]2[C:17](=[O:18])[C:16]3[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=3[S:14]2(=[O:24])=[O:23])[CH:6]=1>CN(C=O)C>[CH3:4][C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]([CH2:12][NH:13][S:14]([C:15]2[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=2[C:17]([O:2][CH3:1])=[O:18])(=[O:24])=[O:23])=[O:25])[CH:6]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To 60 ml DMF is added 13.5 grams (0.25 mole) of sodium methoxide. To this slurry at 15°C. is added a solution of 20 grams (0.062 mole) of 2,3-dihydro-N-(5-methyl-3-isoxazolyl)-3-oxo-1,2-benzisothiazole-2-acetamide 1,1-dioxide dissolved in 70 ml DMF. The reaction mixture is stirred at 25°-30°C. for a half hour whereupon it is acidified and extracted with chloroform. These extracts are washed with sodium bicarbonate and water, dried (na2SO4) and concentrated to an oil which is triturated with petroleum ether to give 16.3 grams (75%) of methyl 2-{[({[(5-methyl-3-isoxazolyl)amino]carbonyl}methyl)amino]sulfonyl}benzoate, mp 153°-156°C.