Benzoylhydrazine → HCID 10198473, compound

HRID 1594256Notes

Reaction equation

HRID 1594256 reaction equation
F[C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[C:4]([C:6]1[O:10][C:9]([C:11]([OH:13])=[O:12])=[CH:8][CH:7]=1)=O.C([NH:26][NH2:27])(=O)C1C=CC=CC=1.CC(C)([O-])C.[K+]>C(O)(=O)C.C(O)C>[C:11]([C:9]1[O:10][C:6]([C:4]2[C:3]3[C:2](=[CH:17][CH:16]=[CH:15][CH:14]=3)[NH:27][N:26]=2)=[CH:7][CH:8]=1)([OH:13])=[O:12]

Participants

6

Reactant 3

HCID 11955BenzoylhydrazineHCID 15408135HCID 15408135, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 10198473HCID 10198473, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent

Procedure

2.5 g (11 mmol) of 5-(2-fluorobenzoyl)furan-2-carboxylic acid, 3.28 g (24 mmol) of benzhydrazide and 2 drops of glacial acetic acid in 50 ml of ethanol were heated under reflux for 10 h. The mixture was subsequently concentrated using a rotary evaporator and the residue was taken up in water, made alkaline using 2 N NaHCO3 solution and extracted with ethyl acetate. The aqueous phase was made acidic using 2 N hydrochloric acid and extracted with ethyl acetate. The combined organic phases were dried and concentrated using a rotary evaporator. The residue was dissolved in 25 ml of THF, 2.74 g (24.2 mmol) of potassium tert-butoxide were added and the mixture was stirred at reflux temperature for 1.5 h. After cooling, the mixture was concentrated using a rotary evaporator and the residue was taken up in 1 N aqueous sodium hydroxide solution and extracted with ethyl acetate. The precipitate that resulted when the aqueous phase was acidified was filtered off with suction, washed with water and dried in a vacuum drying cabinet at 40° C. This gave 1.88 g (75%) of the title compound. m.p.: 205° C. (decomp).

Workup

  1. temperatureunder reflux for 10 h
  2. concentrationThe mixture was subsequently concentrated
  3. customa rotary evaporator
  4. extractionextracted with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. customThe combined organic phases were dried
  7. concentrationconcentrated
  8. customa rotary evaporator
  9. dissolutionThe residue was dissolved in 25 ml of THF
  10. temperatureat reflux temperature for 1.5 h
  11. temperatureAfter cooling
  12. concentrationthe mixture was concentrated
  13. customa rotary evaporator
  14. extractionextracted with ethyl acetate
  15. customThe precipitate that resulted when the aqueous phase
  16. filtrationwas acidified was filtered off with suction
  17. washwashed with water
  18. customdried in a vacuum
  19. customdrying cabinet at 40° C

Sources & evidence

ORD record
ord-7525649a94b346c2b3960d8176f79ed8
Source dataset
uspto-grants-2007_11
Patent number
US07300950B2

Reaction notes

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