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

HRID 248757Notes

Reaction equation

HRID 248757 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-chlorosulfonylbenzoic acid is suspended under exclusion of moisture in 30 ml of dichloromethane, 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 added dropwise thereto. After this dropwise addition has been completed, the mixture is allowed to warm up to room temperature and is agitated for another 12 hours. The thus-produced precipitate is suctioned off and extracted with ether. This ether extract and the filtrate are evaporated together, and the residue is dissolved in dichloroethane. The solution is extracted three times with respectively 10 ml of saturated sodium bicarbonate solution. The combined aqueous extracts are acidified with 2N hydrochloric acid and the thus-precipitated product is removed by filtration. The filter residue is dried under vacuum at 50° C., thus obtaining 3.3 g (9.08 mmol)=90.84% of theory.

Workup

  1. additionAfter this dropwise addition
  2. temperatureto warm up to room temperature
  3. extractionextracted with ether
  4. extractionThis ether extract
  5. customthe filtrate are evaporated together
  6. dissolutionthe residue is dissolved in dichloroethane
  7. extractionThe solution is extracted three times with respectively 10 ml of saturated sodium bicarbonate solution
  8. customthe thus-precipitated product is removed by filtration
  9. customThe filter residue is dried under vacuum at 50° C.
  10. customthus obtaining 3.3 g (9.08 mmol)=90.84% of theory

Sources & evidence

ORD record
ord-f455f0b47ba4490f8e95448c63b1d8a1
Source dataset
uspto-grants-1993_05
Patent number
US05210290

Reaction notes

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