Hydrazine hydrate (1:1) → [4'-Chloro-2-(4-chlorophenyl)acetophenone]hydrazone

HRID 1975651Notes

Reaction equation

HRID 1975651 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.O.[NH2:19][NH2:20]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[N:19][NH2:20])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 5873181,2-Bis(4-chlorophenyl)ethanone

Product 1

HCID 85677177[4'-Chloro-2-(4-chlorophenyl)acetophenone]hydrazoneYield 103.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

1.33 g (5 mmol) of 4'-chloro-2-(4-chlorophenyl)acetophenone was dissolved in 25 ml of ethanol, and 1.25 g (25 mmol) of hydrazine monohydrate was added thereto. The mixture was refluxed under heating for 2 hours. After completion of the reaction, ethanol was distilled off under reduced pressure, and water was added to the residue. The mixture was extracted with dichloromethane. The extract was dried over anhydrous sodium sulfate. Then, the solvent was distilled off to obtain 1.44 g of [4'-chloro-2-(4-chlorophenyl)acetophenone]hydrazone as a yellow oily substance.

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating for 2 hours
  3. distillationwas distilled off under reduced pressure, and water
  4. additionwas added to the residue
  5. extractionThe mixture was extracted with dichloromethane
  6. dry with materialThe extract was dried over anhydrous sodium sulfate
  7. distillationThen, the solvent was distilled off

Sources & evidence

ORD record
ord-c004cabb35fb46b180a1a0bc56a27f2c
Source dataset
uspto-grants-1994_02
Patent number
US05288727

Reaction notes

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