Isopropanol → 4-(Diphenylamino)benzaldehyde N-(2,3-Epoxypropyl)-N-Phenylhydrazone

HRID 1591527Notes

Reaction equation

HRID 1591527 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.[CH:30]([OH:33])([CH3:32])[CH3:31]>>[O:33]1[CH2:32][CH:30]1[CH2:31][N:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[N:8]=[CH:20][C:19]1[CH:18]=[CH:17][C:16]([N:15]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:23][CH:22]=1

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 7516PhenylhydrazineHCID 77846Benzaldehyde, 4-(diphenylamino)-

Product 1

HCID 854347004-(Diphenylamino)benzaldehyde N-(2,3-Epoxypropyl)-N-Phenylhydrazone

Procedure

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

Workup

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

Sources & evidence

ORD record
ord-99fbec5b0d7c445591eef9c61ace86b1
Source dataset
uspto-grants-2007_11
Patent number
US07291431B2

Reaction notes

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