Water → 4-(N,N-dimethylsulphamoyl)-2-trifluoromethylbenzoic acid

HRID 2393014Notes

Reaction equation

HRID 2393014 reaction equation
N(OCCC(C)C)=[O:2].[CH3:9][N:10]([CH3:27])[S:11]([C:14]1[CH:22]=[CH:21][C:17]([C:18](N)=[O:19])=[C:16]([C:23]([F:26])([F:25])[F:24])[CH:15]=1)(=[O:13])=[O:12].O>C(O)(=O)C.S(=O)(=O)(O)O>[CH3:9][N:10]([CH3:27])[S:11]([C:14]1[CH:22]=[CH:21][C:17]([C:18]([OH:2])=[O:19])=[C:16]([C:23]([F:26])([F:25])[F:24])[CH:15]=1)(=[O:13])=[O:12]

Participants

6

Reactant 3

HCID 962WaterHCID 8053Isoamyl NitriteHCID 54168288HCID 54168288, compound

Product 1

HCID 541150674-(N,N-dimethylsulphamoyl)-2-trifluoromethylbenzoic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolvent

Procedure

Isoamyl nitrite (150 ml) was added to a stirred mixture of 4-(N,N-dimethylaminosulphonyl)-2-trifluoromethylbenzamide (15.1 g) in acetic acid and concentrated sulphuric acid while maintaining the temperature at 70°-80° C. It was cooled, poured into water and extracted with ethyl acetate, washed with water, dried (MgSO4) and filtered to give 4-(N,N-dimethylaminosulphonyl)-2-trifluoromethylbenzoic acid (11.2 g) as a white solid, m.p. 188.9°-189.4° C.

Workup

  1. temperaturewhile maintaining the temperature at 70°-80° C
  2. temperatureIt was cooled
  3. extractionextracted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered

Sources & evidence

ORD record
ord-5f8de3c03fcb48a696d41d167eaaff97
Source dataset
uspto-grants-1998_09
Patent number
US05804532

Reaction notes

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