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

HRID 1109702
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인쇄 미리보기

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HRID 1109702 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 176
Acetic Acid
용매
HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cdaef207c0ef4d4dad6fa2b394e5930f
출처 데이터셋
uspto-grants-1994_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05322753

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