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

HRID 2295405Notes

Reaction equation

HRID 2295405 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]=1Cl.[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 94813,4-DichlorobenzotrifluorideHCID 31347SulfolaneHCID 23706288HCID 23706288, compound

Product 1

HCID 39476432-{[2-Chloro-4-(trifluoromethyl)phenyl]amino}-3-methylbutanoic acidYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 10 parts of 3,4-dichlorobenzotrifluoride, 23 parts of potassium valinate and 60 parts of sulfolane was heated and maintained at about 160° C. for about 48 hours, with mixing. The mixture was then cooled to room temperature, diluted with water, 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 10.4 parts of 2-(2-chloro-4-trifluoromethylphenylamino)-3-methylbutanoic acid (85% purity); a yield of about 75% based on the dichlorobenzotrifluoride 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-650e713fdc764303907b42a1cacdf154
Source dataset
uspto-grants-1984_01
Patent number
US04424396

Reaction notes

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