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Potassium Carbonate → N,N'-diphenyl-N-[4-(N-phenyl-N-3-methylphenylamino)-biphenyl-4-yl]benzidine

HRID 481935
Notes
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Reaction equation

HRID 481935 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]([CH3:34])[CH:31]=[CH:32][CH:33]=1.C(=O)([O-])[O-].[K+].[K+]>[Cu].[N+](C1C=CC=CC=1)([O-])=O>[C:19]1([N:18]([C:33]2([N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([CH3:34])[CH:29]=3)[CH:32]=[CH:31][C:30]([C:34]3[CH:10]=[CH:9][CH:8]=[CH:13][CH:12]=3)=[CH:29][CH2:28]2)[C:17]2[CH:25]=[CH:26][C:14]([C:11]3[CH:12]=[CH:13][C:8]([NH:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[CH:9][CH:10]=3)=[CH:15][CH:16]=2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 122683-IodotolueneHCID 68280N,N'-Diphenylbenzidine

Product 1

HCID 86753005N,N'-diphenyl-N-[4-(N-phenyl-N-3-methylphenylamino)-biphenyl-4-yl]benzidineYield 83.6%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalyst
HCID 7416
Nitrobenzene
Solvent

Procedure

A 500-ml reactor was charged with 33.6 g (0.10 mol) of N,N'-diphenylbenzidine, 25.0 g (0.11 mol) of m-iodotoluene, 27.6 g (0.2 mol) of potassium carbonate, 2.6 g of copper powder, and 200 ml of nitrobenzene. In an argon stream, the contents were heated under reflux for 24 hours. At the end of reaction, the insoluble was removed by filtration and the solvent was distilled off from the filtrate. The still residue was purified twice through a silica gel column with a 1/2mixture of n-hexane and toluene, obtaining 28.10 g of N,N'-diphenyl-N-[4-(N-phenyl-N-3-methylphenylamino)-biphenyl-4-yl]benzidine (yield 42%).

Workup

  1. temperatureIn an argon stream, the contents were heated
  2. temperatureunder reflux for 24 hours
  3. customAt the end of reaction
  4. customthe insoluble was removed by filtration
  5. distillationthe solvent was distilled off from the filtrate
  6. customThe still residue was purified twice through a silica gel column with a 1/2mixture of n-hexane and toluene

Sources & evidence

ORD record
ord-f5a2a4faecb346f3b3a380bb69592689
Source dataset
uspto-grants-1998_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05792557

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes