Phenylhydrazine → 4-(Diphenylamino) benzaldehyde phenylhydrazone

HRID 2250303

Reaction equation

HRID 2250303 reaction equation
[C:1]1([NH:7][NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:9]1([N:15]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:16]2[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(O)(C)C>[C:1]1([NH:7][N:8]=[CH:20][C:19]2[CH:18]=[CH:17][C:16]([N:15]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[CH:23][CH:22]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 77846Benzaldehyde, 4-(diphenylamino)-

Product 1

HCID 41696414-(Diphenylamino) benzaldehyde phenylhydrazone

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of phenylhydrazine (0.1 mole, from Aldrich, Milwaukee, Wis.) and 4-(diphenylamino)benzaldehyde (0.1 mole, from Fluka, Buchs SG, Switzerland) was dissolved in 100 ml of isopropanol in a 250 ml, 3-neck round bottom flask equipped with a reflux condenser and a mechanical stirrer. The solution was refluxed for 2 hours. At the end of the reaction, as indicated by the disappearance of the starting materials using thin layer chromatography, the mixture was cooled to room temperature. The 4-(diphenylamino)benzaldehyde phenylhydrazone crystals that formed upon standing were filtered off, washed with isopropanol, and dried in a vacuum oven at 50° C. for 6 hours.

Workup

  1. customequipped with a reflux condenser and a mechanical stirrer
  2. temperatureThe solution was refluxed for 2 hours
  3. customAt the end of the reaction

Sources & evidence

ORD record
ord-c606fbe7591e439fbf0ea8a29efd4dea
Source dataset
uspto-grants-2008_01
Patent number
US07316878B2

Linked notes

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