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 616842Notes

Reaction equation

HRID 616842 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. dry with materialdried (Na2SO4)
  4. concentrationconcentrated to an oil which
  5. customis triturated with petroleum ether

Sources & evidence

ORD record
ord-ad6db90ceaad4a2d9a6133bd4c3318da
Source dataset
uspto-grants-1978_02
Patent number
US04076722

Reaction notes

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