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

HRID 654012Notes

Reaction equation

HRID 654012 reaction equation
Cl[S:2]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[F:14][C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[C:17]([C:22]([F:25])([F:24])[F:23])[CH:16]=1.N1C=CC=CC=1>ClCCl>[F:14][C:15]1[CH:21]=[CH:20][C:18]([NH:19][S:2]([C:5]2[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=2)(=[O:4])=[O:3])=[C:17]([C:22]([F:23])([F:24])[F:25])[CH:16]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 678534-Fluoro-2-(trifluoromethyl)anilineHCID 823854-(Chlorosulfonyl)benzoic acid

Product 1

HCID 150576074-[N-(4-fluoro-2-trifluoromethylphenyl)sulfamoyl]benzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-5 °C

Procedure

2.21 g (10 mmol) of 4-chlorosulfonyl-benzoic acid is suspended in 30 ml of dichloromethane with exclusion of moisture, the suspension is cooled to -5° C and, at this temperature, a solution of 1.79 g (10 mmol) of 4-fluoro-2-(trifluoromethyl)-aniline and 1 ml of pyridine in 20 ml of dichloromethane is instilled. When the instillation is completed, it is allowed to come to room temperature and is stirred for 12 more hours. The resulting precipitate is suctioned off and extracted with ether. The ether extract and the filtrate are concentrated by evaporation together and the residue is dissolved in dichloroethane. The solution is extracted three times with 10 ml of saturated sodium bicarbonate solution each. The combined aqueous extracts are acidified with 2N hydrochloric acid and the product thus precipitating is filtered off. The filter residue is evaporated to dryness in a vacuum at 50° C. 3.3 g (9.08 mmol)=90.84% of the theoretical yield is obtained.

Workup

  1. customto come to room temperature
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. concentrationthe filtrate are concentrated by evaporation together
  5. dissolutionthe residue is dissolved in dichloroethane
  6. extractionThe solution is extracted three times with 10 ml of saturated sodium bicarbonate solution each
  7. customthe product thus precipitating
  8. filtrationis filtered off
  9. customThe filter residue is evaporated to dryness in a vacuum at 50° C
  10. custom3.3 g (9.08 mmol)=90.84% of the theoretical yield
  11. customis obtained

Sources & evidence

ORD record
ord-d1d807d49f7a4d2893cf830394a794a2
Source dataset
uspto-grants-1992_07
Patent number
US05130119

Reaction notes

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