Dimethylformamide → 4-[2-(4-Methoxyphenyl)ethenyl]-N,N-bis(4-methylphenyl)aniline

HRID 2096100Notes

Reaction equation

HRID 2096100 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7]P(=O)(OCC)OCC)=[CH:5][CH:4]=1.[C:18]1([CH3:40])[CH:23]=[CH:22][C:21]([N:24]([C:33]2[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=2)[C:25]2[CH:32]=[CH:31][C:28]([CH:29]=O)=[CH:27][CH:26]=2)=[CH:20][CH:19]=1.CN(C)C=O.C(O[K])(C)(C)C>O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:7]=[CH:39][C:36]2[CH:35]=[CH:34][C:33]([N:24]([C:25]3[CH:32]=[CH:31][C:28]([CH3:29])=[CH:27][CH:26]=3)[C:21]3[CH:22]=[CH:23][C:18]([CH3:40])=[CH:19][CH:20]=3)=[CH:38][CH:37]=2)=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 1707014-(Bis(p-tolyl)amino)benzaldehydeHCID 4063826Diethyl P-((4-methoxyphenyl)methyl)phosphonateHCID 178418922HCID 178418922, compound

Product 1

HCID 538532054-[2-(4-Methoxyphenyl)ethenyl]-N,N-bis(4-methylphenyl)aniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Equal molar amounts of diethyl 4-methoxybenzylphosphonate and 4-(di-p-tolylamino)benzaldehyde were dissolved into N,N-dimethylformamide, and with agitation under water cooling, t-butoxy potassium was added little by little. After agitation for 5 hours at room temperature, water was added, and the solution was rendered acidic so that crude target product precipitates. The crude target product was purified by column chromatography on silica gel to give 4-methoxy-4′-(di-p-tolylamino)stilbene.

Workup

  1. customprecipitates
  2. customThe crude target product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-7afc4de70cdf49d6bf6eaa3dd9c85e82
Source dataset
uspto-grants-2013_05
Patent number
US08450033B2

Reaction notes

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