Potassium Carbonate → HCID 178463141, compound

HRID 963145Notes

Reaction equation

HRID 963145 reaction equation
C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]([F:18])([F:17])[C:9](=O)[CH2:10][C:11]([O:13]CC)=O.C(O)(=O)C(O)=O.[CH2:25]([NH:27][NH2:28])[CH3:26]>C(O)C>[CH2:25]([N:27]1[C:11]([OH:13])=[CH:10][C:9]([C:8]([F:7])([F:17])[F:18])=[N:28]1)[CH3:26]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 96181Hydrazine, ethyl-, ethanedioate (1:1)

Product 1

HCID 178463141HCID 178463141, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 45.0 g of potassium carbonate and 50.0 g (272 mmol) of ethyl 4,4,4-trifluoroacetoacetate in 300 mL of ethanol was cooled with a salt/ice bath to about 0° C. and to this ethylhydrazine oxalate (44.9 g, 299 mmol) was added with a spatula with stirring. After 45 min (minutes) at about 0° C., the mixture was allowed to warm to ambient temperature and stir for 1 hour. It was then heated to reflux overnights The mixture was concentrated by evaporation under reduced pressure and the residue was diluted with dichloromethane and water. The product only partially dissolved and seemed to be distributed in both phases. The layers were separated and the aqueous layer was extracted with dichloromethane and filtered. The solids obtained on filtration were extracted with dichloromethane. The dichloromethane layers and extracts were combined, washed with water (2×200 mL), and dried and the volatiles were allowed to evaporate overnight. All of the solids were combined to obtain the title compound.

Workup

  1. additionwas added with a spatula
  2. stirringstir for 1 hour
  3. temperatureIt was then heated
  4. temperatureto reflux overnights The mixture
  5. concentrationwas concentrated by evaporation under reduced pressure
  6. additionthe residue was diluted with dichloromethane and water
  7. dissolutionThe product only partially dissolved
  8. customThe layers were separated
  9. extractionthe aqueous layer was extracted with dichloromethane
  10. filtrationfiltered
  11. customThe solids obtained on filtration
  12. extractionwere extracted with dichloromethane
  13. washwashed with water (2×200 mL)
  14. customdried
  15. customto evaporate overnight

Sources & evidence

ORD record
ord-34a7d0daad66447f962fa1cfc6eec224
Source dataset
uspto-grants-1998_06
Patent number
US05763359

Reaction notes

Loading…