Ethanol → HCID 54168288, compound

HRID 343034Notes

Reaction equation

HRID 343034 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-4c4cac6f06354823b1cd916bfc974f5d
Source dataset
uspto-grants-1999_01
Patent number
US05859283

Reaction notes

Loading…