Toluene → N,N'-diphenyl-N,N'-bis[3-(2-ethoxycarbonylethyl)phenyl]-[1,1'-biphenyl]-4,4'-diamine

HRID 1451662

Reaktionsgleichung

Reaktionsgleichung von HRID 1451662
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:26]=[CH:25][C:17]([NH:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:16][CH:15]=3)=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[C:28]1[CH:29]=[C:30]([CH:38]=[CH:39][CH:40]=1)[CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34].[C:41](=[O:44])([O-])[O-:42].[K+].[K+].CCCCC[CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH3:59].[C:60]1(C)C=CC=C[CH:61]=1>O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[C:19]1([N:18]([C:58]2[CH:57]=[CH:56][CH:55]=[C:54]([CH2:53][CH2:52][C:41]([O:42][CH2:60][CH3:61])=[O:44])[CH:59]=2)[C:17]2[CH:25]=[CH:26][C:14]([C:11]3[CH:12]=[CH:13][C:8]([N:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[C:28]4[CH:40]=[CH:39][CH:38]=[C:30]([CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH:29]=4)=[CH:9][CH:10]=3)=[CH:15][CH:16]=2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Komponenten

7

Edukt 5

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 12388TridecaneHCID 68280N,N'-DiphenylbenzidineHCID 10913723Ethyl 3-iododihydrocinnamate

Produkt 1

HCID 11125317N,N'-diphenyl-N,N'-bis[3-(2-ethoxycarbonylethyl)phenyl]-[1,1'-biphenyl]-4,4'-diamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24463Copper sulfate pentahydrateKatalysator

Reaktionsbedingungen

Temperatur
230 °C

Versuchsvorschrift

Into a 100-ml flask were introduced 10.77 g of N,N'-diphenylbenzidine, 23.0 g of ethyl 3-iododihydrocinnamate, 11.61 g of potassium carbonate, 1.0 g of copper sulfate pentahydrate, and 20 ml of n-tridecane. The reactants were reacted with heating at 230° C. for 1 hour under an atmosphere of nitrogen. After the reaction, the reaction mixture was cooled to room temperature and then dissolved into 50 ml of toluene. Insolubles were filtered off, and the filtrate was purified by silica gel column chromatography using toluene. As a result, 19.6 g of N,N'-diphenyl-N,N'-bis[3-(2-ethoxycarbonylethyl)phenyl]-[1,1'-biphenyl]-4,4'-diamine was obtained as an oily substance. An IR spectrum of this compound is shown in FIG. 1.

Aufarbeitung

  1. customThe reactants were reacted
  2. customAfter the reaction
  3. temperaturethe reaction mixture was cooled to room temperature
  4. filtrationInsolubles were filtered off
  5. customthe filtrate was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a3077e2c2d60465cb0fac151563a52de
Quelldatensatz
uspto-grants-1997_02
Patentnummer
US05604064

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