Hydrochloric Acid → 2-{[2-Chloro-4-(trifluoromethyl)phenyl]amino}-3-methylbutanoic acid

HRID 2295406Notes

Reaction equation

HRID 2295406 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:6][C:7]=1F.[NH2:13][C@H:14]([C:18]([O-:20])=[O:19])[CH:15]([CH3:17])[CH3:16].[K+].S1(CCCC1)(=O)=O.Cl>O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:6][C:7]=1[NH:13][CH:14]([CH:15]([CH3:17])[CH3:16])[C:18]([OH:20])=[O:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 31347SulfolaneHCID 157153Benzene, 2-chloro-1-fluoro-4-(trifluoromethyl)-HCID 23706288HCID 23706288, compound

Product 1

HCID 39476432-{[2-Chloro-4-(trifluoromethyl)phenyl]amino}-3-methylbutanoic acidYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 10 parts of 3-chloro-4-fluorobenzotrifluoride, 10 parts of potassium valinate and 50 parts of sulfolane was heated and maintained at about 125° C. for about 17 hours, with mixing. The mixture was then cooled to room temperature, diluted with water and acidified with hydrochloric acid to a pH of 1.0. The aqueous layer was extracted with diethyl ether. The ether layers were washed with water, then dried and concentrated by evaporation to yield 9.6 parts of 2-(2-chloro-4-trifluoromethylphenylamino)-3-methylbutanoic acid (96% purity); a yield of about 65% based on the 3-chloro-4-fluorobenzotrifluoride starting material.

Workup

  1. temperaturewas heated
  2. additionwith mixing
  3. temperatureThe mixture was then cooled to room temperature
  4. extractionThe aqueous layer was extracted with diethyl ether
  5. washThe ether layers were washed with water
  6. customdried
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-471c87b11b8a4c008f06765db3f8d0a9
Source dataset
uspto-grants-1984_01
Patent number
US04424396

Reaction notes

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