Hydrogen Peroxide → HCID 54168288, compound

HRID 2393015Notes

Reaction equation

HRID 2393015 reaction equation
[OH:1]O.[CH3:3][N:4]([CH3:20])[S:5]([C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([C:16]([F:19])([F:18])[F:17])[CH:9]=1)(=[O:7])=[O:6].[OH-].[Na+].[Cl-].[Na+]>C(O)C.O>[CH3:3][N:4]([CH3:20])[S:5]([C:8]1[CH:15]=[CH:14][C:11]([C:12]([NH2:13])=[O:1])=[C:10]([C:16]([F:17])([F:19])[F:18])[CH:9]=1)(=[O:6])=[O:7]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 54075582HCID 54075582, compound

Product 1

HCID 54168288HCID 54168288, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Hydrogen peroxide (30%, 100 ml) was added to a stirred mixture of 4-(N,N-dimethylaminosulphonyl)-2-trifluoromethylbenzonitrile (20.37 g) and sodium hydroxide (1.0 g) in ethanol under an inept atmosphere maintaining the temperature at 40°-45° C. The mixture was stirred and heated at that temperature for 3.5 hours. It was cooled, poured into water, sodium chloride was added and it was extracted with ethyl acetate, washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was re-crystallized from a mixture of ethyl acetate and toluene to give 4-(N,N-dimethylaminosulphonyl)-2-trifluoromethylbenzamide (16.44 g) as white crystals, m.p. 149°-156° C.

Workup

  1. temperaturemaintaining the temperature at 40°-45° C
  2. temperatureheated at that temperature for 3.5 hours
  3. temperatureIt was cooled
  4. additionwas added
  5. extractionit was extracted with ethyl acetate
  6. washwashed with water
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customThe filtrate was evaporated to dryness
  10. customthe residue was re-crystallized from a mixture of ethyl acetate and toluene

Sources & evidence

ORD record
ord-950da05116ff4a3386b611e85aafdb4d
Source dataset
uspto-grants-1998_09
Patent number
US05804532

Reaction notes

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