Water → Glycine, N-ethyl-N-(3-methylphenyl)-, 2,2,2-trifluoroethyl ester

HRID 904880Notes

Reaction equation

HRID 904880 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[CH:5]=1)[CH3:2].Br[CH2:12][C:13]([O:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[O:14].C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O>[CH2:1]([N:3]([CH2:12][C:13]([O:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[CH:5]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 7603N-ethyl-3-methylanilineHCID 11430Potassium CarbonateHCID 109083Acetic acid, 2-bromo-, 2,2,2-trifluoroethyl ester

Product 1

HCID 174709Glycine, N-ethyl-N-(3-methylphenyl)-, 2,2,2-trifluoroethyl esterYield 94.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 13.5 g (0.1 mole) N-ethyl-m-toluidine, 22.1 g (0.1 mole) trifluoroethyl bromoacetate and 7.0 g (0.051 mole) potassium carbonate in 100 ml of acetone was heated at reflux for two hours. Water (10 ml) was added and the mixture heated at reflux overnight. Solvent was removed on a rotary evaporator, ether added and the layers separated. The aqueous layer was extracted with ether. The combined ether solution was washed once with 50 ml of water and dried over sodium sulfate. Removal of ether gave 26.0 g brown oil which gave one spot by thin layer chromatography and was used as isolated (94%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for two hours
  3. temperaturethe mixture heated
  4. temperatureat reflux overnight
  5. customSolvent was removed on a rotary evaporator, ether
  6. additionadded
  7. customthe layers separated
  8. extractionThe aqueous layer was extracted with ether
  9. washThe combined ether solution was washed once with 50 ml of water
  10. dry with materialdried over sodium sulfate
  11. customRemoval of ether

Sources & evidence

ORD record
ord-2849c7a568ff44aaae692e906ddf9e8b
Source dataset
uspto-grants-1983_12
Patent number
US04420555

Reaction notes

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