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

HRID 1287959Notes

Reaction equation

HRID 1287959 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]=1

Participants

4

Reactant 2

HCID 24255921,2-Benzisothiazole-2(3H)-acetamide, N-(5-methyl-3-isoxazolyl)-3-oxo-, 1,1-dioxideHCID 10942334Sodium Methoxide

Product 1

HCID 12890328Methyl 2-{[({[(5-methyl-3-isoxazolyl)amino]carbonyl}methyl)amino]sulfonyl}benzoateYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

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.

Workup

  1. extractionextracted with chloroform
  2. washThese extracts are washed with sodium bicarbonate and water
  3. customdried (na2SO4)
  4. concentrationconcentrated to an oil which
  5. customis triturated with petroleum ether

Sources & evidence

ORD record
ord-be2024ebd6594496a82537f2a6378bf1
Source dataset
uspto-grants-1976_10
Patent number
US03987038

Reaction notes

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