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

HRID 964521

Reaktionsgleichung

Reaktionsgleichung von HRID 964521
[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

Versuchsvorschrift

Into a 100 ml flask were placed 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, and they were thermally reacted under an atmosphere of N2 at 230° C. for 1 hour. After the reaction, the reaction mixture was cooled down to room temperature, dissolved in 50 ml of toluene, the insolubles were filtered, and the filtrate was purified by silica gel chromatography using toluene. This gave 19.6 g of N,N'-diphenyl-N,N'-bis[3-(2-ethoxycarbonylethyl)phenyl]-[1,1'-biphenyl]-4,4'-diamine in an oily state.

Aufarbeitung

  1. customInto a 100 ml flask were placed
  2. customAfter the reaction
  3. filtrationthe insolubles were filtered
  4. customthe filtrate was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c3bcf4efd09743c789f4d0e56ee148f1
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05770339

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