Hydrochloric Acid → 2-Chloro-5-({[1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazol-5-yl]carbonyl}amino)benzoic acid

HRID 2274013Notes

Reaction equation

HRID 2274013 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([C:15]2[N:19]([CH3:20])[N:18]=[C:17]([C:21]([F:27])([F:26])[C:22]([F:25])([F:24])[F:23])[C:16]=2[C:28]([F:31])([F:30])[F:29])=[O:14])=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[OH-].[Na+].Cl>CO>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([C:15]2[N:19]([CH3:20])[N:18]=[C:17]([C:21]([F:27])([F:26])[C:22]([F:25])([F:23])[F:24])[C:16]=2[C:28]([F:29])([F:30])[F:31])=[O:14])=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86660079methyl 2-chloro-5-({[1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazol-5-yl]carbonyl}amino)benzoate

Product 1

HCID 462196652-Chloro-5-({[1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazol-5-yl]carbonyl}amino)benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5.75 g (11.9 mmol) of methyl 2-chloro-5-({[1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazol-5-yl]carbonyl}amino)benzoate are dissolved in 30 ml of methanol p.A., and 15.0 ml (30.0 mmol) of 2 N aqueous sodium hydroxide solution are then added. The reaction mixture is stirred at room temperature for 16 hours. The reaction solution is acidified carefully with 6 N hydrochloric acid, and the aqueous phase is then extracted three times with ethyl acetate. The combined organic phases are washed once with saturated sodium chloride solution, dried over sodium sulphate and filtered. The solvent is removed under reduced pressure on a rotary evaporator. This gives 5.57 g of 2-chloro-5-({[1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazol-5-yl]carbonyl}amino)benzenecarboxylic acid as a colourless solid.

Workup

  1. extractionthe aqueous phase is then extracted three times with ethyl acetate
  2. washThe combined organic phases are washed once with saturated sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customThe solvent is removed under reduced pressure on a rotary evaporator

Sources & evidence

ORD record
ord-01fbd53a8616444ba4e080893ec11ecc
Source dataset
uspto-grants-2015_09
Patent number
US09126945B2

Reaction notes

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