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

HRID 3024

Reaction equation

HRID 3024 reaction equation
[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

Participants

7

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 24463Copper sulfate pentahydrateCatalyst

Conditions

Temperature
230 °C

Procedure

In a 100 ml-volume flask, 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 were placed, and the mixture was reacted under heating at 230° C. for one hour in a nitrogen stream. After the reaction, the system was cooled to room temperature, the reaction mixture was dissolved in 50 ml of toluene, insoluble matters were filtered and the filtrate was purified by silica gel column chromatography using toluene to obtain 19.6 g of N,N'-diphenyl-N,N'-bis[3-(2-ethoxycarbonylethyl)phenyl]-[1,1'-biphenyl]-4,4'-diamine as an oily substance. The IR spectrum of the product is shown in FIG. 2.

Workup

  1. customthe mixture was reacted
  2. customAfter the reaction
  3. temperaturethe system was cooled to room temperature
  4. filtrationinsoluble matters were filtered
  5. customthe filtrate was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-70576781abfa4a2db8a2ad21736fa5f6
Source dataset
uspto-grants-1998_03
Patent number
US05731118

Linked notes

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