Acetic Acid → N-[2-(2,3,4,5-tetramethylcyclopentadienyl)phenylmethylene]-N-(2,4,6-trimethylphenyl)amine

HRID 15707

Reaction equation

HRID 15707 reaction equation
[CH3:1][C:2]1[CH:3]([C:10]2[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=2[CH:12]=O)[C:4]([CH3:9])=[C:5]([CH3:8])[C:6]=1[CH3:7].C(O)(=O)C.[CH3:22][C:23]1[CH:29]=[C:28]([CH3:30])[CH:27]=[C:26]([CH3:31])[C:24]=1[NH2:25]>C(O)C>[CH3:1][C:2]1[CH:3]([C:10]2[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=2[CH:12]=[N:25][C:24]2[C:26]([CH3:31])=[CH:27][C:28]([CH3:30])=[CH:29][C:23]=2[CH3:22])[C:4]([CH3:9])=[C:5]([CH3:8])[C:6]=1[CH3:7]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 69132,4,6-TrimethylanilineHCID 1317271152-(2,3,4,5-Tetramethylcyclopentadienyl)benzaldehyde

Product 1

HCID 131727122N-[2-(2,3,4,5-tetramethylcyclopentadienyl)phenylmethylene]-N-(2,4,6-trimethylphenyl)amineYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-(2,3,4,5-tetramethylcyclopentadienyl)benzaldehyde (10.0 mmol) in ethanol (30.0 mL) were added dropwise acetic acid (1.0 mmol) and 2,4,6-trimethylaniline (10.5 mmol) under a nitrogen atmosphere. 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-(2,4,6-trimethylphenyl)amine (3.43 g, yield 100%).

Workup

  1. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-9c8ddf35dcdf4954a680fb39a6d6cc76
Source dataset
uspto-grants-2010_06
Patent number
US07732643B2

Linked notes

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