Aniline → N-[2-(2,3,4,5-tetramethylcyclopentadienyl)phenylmethylene]-N-phenylamine

HRID 15701Notes

Reaction equation

HRID 15701 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:8][C:9]1[CH:10]([C:17]2[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=2[CH:19]=O)[C:11]([CH3:16])=[C:12]([CH3:15])[C:13]=1[CH3:14]>C(O)C>[CH3:8][C:9]1[CH:10]([C:17]2[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=2[CH:19]=[N:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:11]([CH3:16])=[C:12]([CH3:15])[C:13]=1[CH3:14]

Participants

4

Reactant 2

HCID 6115AnilineHCID 1317271152-(2,3,4,5-Tetramethylcyclopentadienyl)benzaldehyde

Product 1

HCID 131727117N-[2-(2,3,4,5-tetramethylcyclopentadienyl)phenylmethylene]-N-phenylamineYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under a nitrogen atmosphere, aniline (31.5 mmol) was added dropwise to a solution of 2-(2,3,4,5-tetramethylcyclopentadienyl)benzaldehyde (30.0 mmol) in ethanol (90.0 mL) and the mixture was stirred at room temperature. After disappearance of the aldehyde was confirmed by gas chromatography, the solvent was distilled off under reduced pressure to give N-[2-(2,3,4,5-tetramethylcyclopentadienyl)phenylmethylene]-N-phenylamine (9.00 g, yield 100%).

Workup

  1. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-46925424d66a43f6b52df972eddbeaa8
Source dataset
uspto-grants-2010_06
Patent number
US07732643B2

Reaction notes

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