Dimethylformamide → 4-[2-(4-Methoxyphenyl)ethenyl]-N,N-diphenylaniline

HRID 975174Notes

Reaction equation

HRID 975174 reaction equation
[C:1]1([N:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]2[CH:15]=[CH:14][C:11](C=O)=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(=O)([O-])O[C:24](CC)([CH2:33]C)[C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1.CN(C)C=O.C[O-].[Na+]>O.C(O)(=O)C>[C:16]1([N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8]2[CH:9]=[CH:10][C:11]([CH:33]=[CH:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)=[CH:14][CH:15]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 77846Benzaldehyde, 4-(diphenylamino)-HCID 10942334Sodium MethoxideHCID 178447637HCID 178447637, compound

Product 1

HCID 539715084-[2-(4-Methoxyphenyl)ethenyl]-N,N-diphenylanilineYield 61.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 54.6 g (0.2 mol) of 4-diphenylaminobenzaldehyde, 51.6 g (0.2 mol) of diethyl-4-methoxybenzyl phosphonate, and 250 ml of dimethylformamide was placed in a 500 ml four-neck flask. 57.9 g of 28% sodium methylate was added dropwise to the above mixture with stirring at room temperature over a period of 15 minutes. Thus, the reaction was carried out at 50°to 60° C. for five hours. The thus obtained reaction mixture was diluted with 500 ml of water, and then made acid with the addition of acetic acid. Then the mixture was filtrated to obtain a wet cake. The thus obtained wet cake was washed with 100 ml of methanol three times, and recrystallized from a mixed solvent of ethanol and dioxane, whereby 46.2 g of 4-diphenylamino-4'-methoxystilbene was obtained as yellow crystals in the form of needles in a yield of 61.3%. The melting point of the obtained compound was 170° to 171.5° C.

Workup

  1. customwas placed in a 500 ml four-neck flask
  2. waitThus, the reaction was carried out at 50°to 60° C. for five hours
  3. customThe thus obtained reaction mixture
  4. filtrationThen the mixture was filtrated
  5. customto obtain a wet cake
  6. washThe thus obtained wet cake was washed with 100 ml of methanol three times
  7. customrecrystallized from a mixed solvent of ethanol and dioxane

Sources & evidence

ORD record
ord-caf17bc72fa542e7bf0c886610f19372
Source dataset
uspto-grants-1997_03
Patent number
US05608010

Reaction notes

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