Cinnamoylbenzene → HCID 3798265, compound

HRID 1160047Notes

Reaction equation

HRID 1160047 reaction equation
[OH-].[K+].[C:3]1([CH:9]=[CH:10][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=O)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:19]1([NH:25][NH2:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(O)C>[C:19]1([N:25]2[CH:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:10]=[C:9]([C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)[NH:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7189CinnamoylbenzeneHCID 7516PhenylhydrazineHCID 14797Potassium Hydroxide2×

Product 1

HCID 3798265HCID 3798265, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 2000-ml four-necked flask were placed 13.0 g (0.23 mole) of potassium hydroxide and 1004.5 g of ethanol. The mixture was stirred at room temperature until the potassium hydroxide dissolved and 25.8 g (0.12 mole) of chalcone and 26.4 g (0.24 mole) of phenylhydrazine were added at room temperature. After the addition, the mixture was heated under reflux with stirring for three hours. Upon completion of the reaction, the reaction mixture was cooled to room temperature and a solid was recovered by filtration. The solid was washed with hexane and dried under reduced pressure to give 27.8 g of 1,3,5-triphenylpyrazoline as a white powder.

Workup

  1. customIn a 2000-ml four-necked flask were placed
  2. dissolutiondissolved
  3. additionAfter the addition
  4. temperaturethe mixture was heated
  5. temperatureunder reflux
  6. customUpon completion of the reaction
  7. filtrationa solid was recovered by filtration
  8. washThe solid was washed with hexane
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-be67a1ee88c24337bf186b75a04b87a9
Source dataset
uspto-grants-2010_10
Patent number
US07816020B2

Reaction notes

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