Sodium Hydroxide → 2-[N-(4-fluoro-2-trifluoromethylphenyl)sulfamoyl]benzoic acid

HRID 248751Notes

Reaction equation

HRID 248751 reaction equation
C[O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10](=[O:24])(=[O:23])[NH:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[C:19]([F:22])([F:21])[F:20].[OH-].[Na+]>O1CCOCC1>[F:18][C:15]1[CH:16]=[CH:17][C:12]([NH:11][S:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([OH:25])=[O:2])(=[O:24])=[O:23])=[C:13]([C:19]([F:22])([F:20])[F:21])[CH:14]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 539726942-[N-(4-Fluoro-2-trifluoromethylphenyl)sulfamoyl]benzoic Acid Methyl Ester

Product 1

HCID 197639992-[N-(4-fluoro-2-trifluoromethylphenyl)sulfamoyl]benzoic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

6,25 g (16.56 mmol) of 2-[N-(4-fluoro-2-trifluoromethylphenyl)sulfamoyl]benzoic acid methyl ester is dissolved in 60 ml of dioxane and combined with 25 ml (50 mmol) of 2N sodium hydroxide solution. The mixture is heated on a water bath until all of the starting material has disappeared. The solution is then concentrated to dryness under vacuum, combined with 2N hydrochloric acid, and the thus-precipitated material is dissolved in ethyl acetate. The organic solution is dried over sodium sulfate, concentrated to dryness, and the residue is crystallized from ethyl acetate/hexane. The title compound melts at 148° C.

Workup

  1. temperatureThe mixture is heated on a water bath until all of the starting material
  2. concentrationThe solution is then concentrated to dryness under vacuum
  3. dissolutionthe thus-precipitated material is dissolved in ethyl acetate
  4. dry with materialThe organic solution is dried over sodium sulfate
  5. concentrationconcentrated to dryness
  6. customthe residue is crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-cc6f07ac2e4846b7a5d09b9954989b53
Source dataset
uspto-grants-1993_05
Patent number
US05210290

Reaction notes

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