Ethyl trifluoroacetate → HCID 13565664, compound

HRID 1589386Notes

Reaction equation

HRID 1589386 reaction equation
[Na].[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C:3]1=[O:11].[F:12][C:13]([F:20])([F:19])[C:14](OCC)=[O:15]>C(O)C>[F:12][C:13]([F:20])([F:19])[C:14]([CH:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[NH:2][C:3]1=[O:11])=[O:15]

Participants

5

Reactant 3

HCID 9794Ethyl trifluoroacetateHCID 321710OxindoleHCID 5360545Sodium

Product 1

HCID 13565664HCID 13565664, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium (3.0 g, 0.13 mole) was dissolved in 150 ml of ethanol, and then 13.3 g (0.10 mole) of 2-oxindole was added at room temperature, with stirring. The resulting mixture was cooled in an ice-bath and 18.5 g (0.13 mole) of ethyl 2,2,2-trifluoroacetate was added rapidly with stirring. The cooling bath was removed, and the reaction mixture was heated to the reflux temperature of the solvent and held there for 1 hour. At this point, the reaction mixture was cooled and the bulk of the solvent was removed by evaporation in vacuo. The residue was added to 300 ml of water, to which was then added 100 ml of concentrated hydrochloric acid. The resulting mixture was cooled in an ice-bath and then the solid was collected by filtration. The latter solid was dissolved in ethyl acetate, and the ethyl acetate solution was washed with saturated sodium chloride and then dried using magnesium sulfate. The dried solution was evaporated in vacuo, and the residue was recrystallized from toluene, to give 13.2 g of the title compound as yellow crystals, m.p. 183.5°-184.5° C.

Workup

  1. temperatureThe resulting mixture was cooled in an ice-bath
  2. stirringwith stirring
  3. customThe cooling bath was removed
  4. temperaturethe reaction mixture was heated to the reflux temperature of the solvent
  5. temperatureAt this point, the reaction mixture was cooled
  6. customthe bulk of the solvent was removed by evaporation in vacuo
  7. additionThe residue was added to 300 ml of water, to which
  8. additionwas then added 100 ml of concentrated hydrochloric acid
  9. temperatureThe resulting mixture was cooled in an ice-bath
  10. filtrationthe solid was collected by filtration
  11. dissolutionThe latter solid was dissolved in ethyl acetate
  12. washthe ethyl acetate solution was washed with saturated sodium chloride
  13. customdried
  14. customThe dried solution was evaporated in vacuo
  15. customthe residue was recrystallized from toluene

Sources & evidence

ORD record
ord-73d88a8101da453fa37067044d678f2e
Source dataset
uspto-grants-1986_02
Patent number
US04569942

Reaction notes

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