Methanol → Methyl 2-aMino-2-(4-(trifluoroMethyl)phenyl)acetate

HRID 458924Notes

Reaction equation

HRID 458924 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:13]=[CH:12][C:6]([CH:7]([NH2:11])[C:8]([OH:10])=[O:9])=[CH:5][CH:4]=1.S(Cl)(Cl)=O.[CH3:20]O>>[F:1][C:2]([F:14])([F:15])[C:3]1[CH:13]=[CH:12][C:6]([CH:7]([NH2:11])[C:8]([O:10][CH3:20])=[O:9])=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 2777632Amino[4-(trifluoromethyl)phenyl]acetic acid

Product 1

HCID 18442492Methyl 2-aMino-2-(4-(trifluoroMethyl)phenyl)acetateYield 69%

Procedure

4-Trifluoromethyl-α-carboxybenzylamine (1.4 g, 1.83 mmol) and thionylchloride were added to methanol (8 ml) and the mixture was refluxed for 2 h. The solvent was evaporated under reduced pressure. The residue was suspended in diethyl ether and the product was filtered off, washed with ether and dried to give the title compound 0.34 g (69%).

Workup

  1. temperaturethe mixture was refluxed for 2 h
  2. customThe solvent was evaporated under reduced pressure
  3. filtrationthe product was filtered off
  4. washwashed with ether
  5. customdried

Sources & evidence

ORD record
ord-2a74959174da444eb9b2e0aa45c09bc5
Source dataset
uspto-grants-2007_03
Patent number
US07192945B2

Reaction notes

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