Acetic Acid → 1-(4-Bromophenyl)-2-cyclohexylidenehydrazine

HRID 659630Notes

Reaction equation

HRID 659630 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.[C:11]1(=O)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.C(O)(=O)C.CCOC(C)=O>CCO>[Br:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][N:10]=[C:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7967CyclohexanoneHCID 8857Ethyl AcetateHCID 121574-Bromophenylhydrazine hydrochloride

Product 1

HCID 41672531-(4-Bromophenyl)-2-cyclohexylidenehydrazineYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
105 °C

Procedure

A 250-mL round-bottomed flask was charged with 1-(4-bromophenyl)hydrazine hydrochloride (10 g, 45.05 mmol, 1.00 equiv) in EtOH (120 mL). To this was added cyclohexanone (8.8 g, 89.80 mmol, 2.00 equiv) and acetic acid (2.7 g, 45.00 mmol, 1.00 equiv). The resulting mixture was heated to 105° C. in an oil bath for about 1 hour. The reaction progress was monitored by TLC (EtOAc:PE=1:1). Upon completion, the reaction mixture was cooled down to room temperature and filtered off to obtain 1-(4-bromophenyl)-2-cyclohexylidenehydrazine as a yellow solid (11 g, 92%).

Workup

  1. temperatureUpon completion, the reaction mixture was cooled down to room temperature
  2. filtrationfiltered off

Sources & evidence

ORD record
ord-0070776a323643a1aaff854f6b68ae38
Source dataset
uspto-grants-2011_12
Patent number
US08080566B1

Reaction notes

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