Nitrobenzene → HCID 22016282, compound

HRID 725740Notes

Reaction equation

HRID 725740 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11](I)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[N+:21]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([O-])=O>[Cu]>[C:24]1([N:21]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:13]=[CH:12][C:11]([N:21]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[C:2]4[CH:7]=[CH:6][C:5]([C:8]5[CH:9]=[CH:10][C:11]([N:21]([C:2]6[CH:7]=[CH:6][C:5]([C:8]7[CH:9]=[CH:10][C:11]([N:21]([C:2]8[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=8)[C:24]8[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=8)=[CH:12][CH:13]=7)=[CH:4][CH:3]=6)[C:24]6[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=6)=[CH:12][CH:13]=5)=[CH:4][CH:3]=4)=[CH:10][CH:9]=3)=[CH:4][CH:3]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 7416NitrobenzeneHCID 11430Potassium CarbonateHCID 763484,4'-Diiodo-1,1'-biphenyl

Product 1

HCID 22016282HCID 22016282, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

8.66 g (0.021 mol) of N,N,N'-triphenylbenzidine thus obtained, 4.06 g (0.01 mol) of 4,4'-diiodobiphenyl, 2.90 g (0.021 mol) of anhydrous potassium carbonate, 0.32 g (0.005 mol) of copper powder, and 10 ml of nitrobenzene were mixed. The reaction mixture was then allowed to undergo reaction at a temperature of 195° C. to 210° C. for 20 hours. The reaction product was then extracted with 140 ml of toluene. The insoluble contents were removed by filtration. The filtrate was then concentrated. To the concentrate was then added 120 ml of n-hexane to recover a crude crystal. The crude crystal thus recovered was then purified by column chromatography (carrier: silica gel; elute: 1/2 mixture of toluene and n-hexane) to obtain 4.73 g (yield: 48.5%) of N,N'-bis(4'-diphenylamino-4-biphenylyl)-N,N'-diphenylbenzidine. The melting point of the product was from 242.5° C. to 243.5° C.

Workup

  1. customreaction at a temperature of 195° C. to 210° C. for 20 hours
  2. extractionThe reaction product was then extracted with 140 ml of toluene
  3. customThe insoluble contents were removed by filtration
  4. concentrationThe filtrate was then concentrated
  5. additionTo the concentrate was then added 120 ml of n-hexane
  6. customto recover a crude crystal
  7. customThe crude crystal thus recovered
  8. customwas then purified by column chromatography (carrier: silica gel; elute: 1/2 mixture of toluene and n-hexane)

Sources & evidence

ORD record
ord-a91496117935408cb635b5038161b98e
Source dataset
uspto-grants-1998_01
Patent number
US05707747

Reaction notes

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