Acetic Acid → HCID 21548765, compound

HRID 1605098Notes

Reaction equation

HRID 1605098 reaction equation
[C:1]([N:9]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[F:24])N=CC1C=CC=CC=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:25]1[CH:31]([C:32]([OH:34])=[O:33])[CH2:30][CH2:29][C:27](=O)[CH2:26]1.C(O)(=O)C.Cl>O>[C:1]([N:9]1[C:27]2[CH2:26][CH2:25][CH:31]([C:32]([OH:34])=[O:33])[CH2:30][C:29]=2[C:23]2[C:18]1=[C:19]([F:24])[CH:20]=[CH:21][CH:22]=2)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic Acid4×HCID 313Hydrochloric Acid3×HCID 1927304-Oxocyclohexanecarboxylic acidHCID 68140271HCID 68140271, compound

Product 1

HCID 21548765HCID 21548765, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 6.4 g. benzaldehyde 1-benzoyl-1-(2-fluorophenyl)hydrazone and 5.35 g. of cyclohexanone-4-carboxylic acid in 50 ml. glacial acetic acid and 10 ml. of glacial acetic acid saturated with hydrogen chloride was heated under reflux for two hours. An additional 10 ml. glacial acetic acid saturated with hydrogen chloride was then added and heating under reflux was continued two additional hours. A further 5 ml. glacial acetic acid saturated with hydrogen chloride was added and heating under reflux was continued another two hours. The mixture was cooled, 25 ml. water was added portion-wise, and the resulting solid was collected by filtration and washed with water to yield 3.54 g. of the title compound; m.p. 250°-251°C. (acetic acid-water).

Workup

  1. temperatureunder reflux for two hours
  2. temperatureheating
  3. temperatureunder reflux
  4. temperatureheating
  5. temperatureunder reflux
  6. temperatureThe mixture was cooled
  7. filtrationthe resulting solid was collected by filtration
  8. washwashed with water
  9. customto yield 3.54 g

Sources & evidence

ORD record
ord-b1cfa8abab724d7aa9f89a3dff178339
Source dataset
uspto-grants-1976_04
Patent number
US03948939

Reaction notes

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