Dimethylformamide → 1,2-Benzisothiazole-2(3H)-acetamide, N-(5-methyl-3-isoxazolyl)-3-oxo-, 1,1-dioxide

HRID 1076524Notes

Reaction equation

HRID 1076524 reaction equation
CN(C=O)C.Cl[N:7]([C:11]1[CH:15]=[C:14]([CH3:16])[O:13][N:12]=1)[C:8]([CH3:10])=[O:9].O.O.[S:19]1([C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:23](=[O:24])[NH:22]1)(=[O:21])=[O:20].[Na]>O>[CH3:16][C:14]1[O:13][N:12]=[C:11]([NH:7][C:8](=[O:9])[CH2:10][N:22]2[C:23](=[O:24])[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:30]=3[S:19]2(=[O:20])=[O:21])[CH:15]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 203243743-(Chloroacetamino)-5-methylisoxazoleHCID 46942257CID 46942257

Product 1

HCID 24255921,2-Benzisothiazole-2(3H)-acetamide, N-(5-methyl-3-isoxazolyl)-3-oxo-, 1,1-dioxideYield 74.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To 2.31 liters of DMF is added 479 grams (2.75 moles) of 3-(chloroacetamino)-5-methylisoxazole followed by 669 grams (2.9 moles) of sodium saccharin dihydrate. The mixture is heated to 100°C. and this temperature is maintained for 2 hours. The cooled reaction mixture is poured into 8 liters of water, filtered and the wet cake is recrystallized from 15 liters of ethanol to give 658 grams (74.8%) of 2,3,dihydro-N-(5-methyl-3-isoxazolyl)-3-oxo-1,2-benzisothiazole-2-acetamide 1,1-dioxide, mp 218°-220°C.; I.R. and NMR spectra are consistant with the structure.

Workup

  1. temperaturethis temperature is maintained for 2 hours
  2. customThe cooled reaction mixture
  3. filtrationfiltered
  4. customthe wet cake is recrystallized from 15 liters of ethanol

Sources & evidence

ORD record
ord-eb88a8944e734d38b944c73b1e9020ec
Source dataset
uspto-grants-1976_05
Patent number
US03957772

Reaction notes

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