Ethanol → HCID 54168288, compound

HRID 266592Notes

Reaction equation

HRID 266592 reaction equation
[CH3:1][N:2]([CH3:18])[S:3]([C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[C:8]([C:14]([F:17])([F:16])[F:15])[CH:7]=1)(=[O:5])=[O:4].[OH-].[Na+].C([OH:23])C.OO>O>[CH3:1][N:2]([CH3:18])[S:3]([C:6]1[CH:13]=[CH:12][C:9]([C:10]([NH2:11])=[O:23])=[C:8]([C:14]([F:15])([F:17])[F:16])[CH:7]=1)(=[O:4])=[O:5]

Participants

6

Reactant 4

HCID 702EthanolHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 54075582HCID 54075582, compound

Product 1

HCID 54168288HCID 54168288, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 4-(N,N-dimethylsulphamoyl)-2-trifluoromethylbenzonitrile (2.78 g), sodium hydroxide (130 mg) and ethanol was heated to 40° C. Hydrogen peroxide (7 ml of 30% solution) was then added and the mixture heated at 40° C. for 3 hours. After cooling the mixture was poured into water and extracted with ethyl acetate. The organic phase was washed with water, dried (anhydrous magnesium sulphate) and filtered. The filtrate was evaporated to dryness and the residue recrystallised from ethyl acetate/toluene to give 4-(N,N-dimethylsulphamoyl)-2-trifluoromethylbenzamide (1.39 g) as a white solid, m.p. 149°-156° C.

Workup

  1. temperaturethe mixture heated at 40° C. for 3 hours
  2. temperatureAfter cooling the mixture
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with water
  5. dry with materialdried (anhydrous magnesium sulphate)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness
  8. customthe residue recrystallised from ethyl acetate/toluene

Sources & evidence

ORD record
ord-988db69d07614bdc94db22bc88db36ed
Source dataset
uspto-grants-1997_07
Patent number
US05650533

Reaction notes

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