Nitrobenzene → HCID 19064203, compound

HRID 481934Notes

Reaction equation

HRID 481934 reaction equation
I[C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[N+:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([O-])=O>[Cu]>[C:23]1([N:20]([C:10]2[CH:9]=[C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:2][CH:3]=3)[CH:13]=[CH:12][CH:11]=2)[C:7]2[CH:6]=[CH:5][C:4]([C:8]3[CH:13]=[CH:12][C:11]([N:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:10]4[CH:9]=[C:8]([C:4]5[CH:5]=[CH:6][CH:7]=[CH:2][CH:3]=5)[CH:13]=[CH:12][CH:11]=4)=[CH:10][CH:9]=3)=[CH:3][CH:2]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7416NitrobenzeneHCID 11430Potassium CarbonateHCID 885421,1'-Biphenyl, 3-iodo-

Product 1

HCID 19064203HCID 19064203, compoundYield 78.89%

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

300-ml reactor was charged with 10 q (0.0298 mol) of N,N'-diphenylbenzidie, 25 g (0.0893 mol) of m-iodobiphenyl, 12.3 g (0.0891 mol) of potassium carbonate, 2.6 g of copper powder, and 150 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 through a silica gel column with a 5/1 mixture of n-hexane and ethyl acetate, obtaining 15 g of N,N'-diphenyl-N,N'-di(3-biphenylyl)benzidine of primary purity grade (yield 78.89%. It was further purified by recrystallization from toluene and train sublimation, obtaining 10.6 g of a 99.9% pure product (yield 55.6%). Further purification by sublimation yielded a 99,99% pure product.

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 through a silica gel column with a 5/1 mixture of n-hexane and ethyl acetate

Sources & evidence

ORD record
ord-dadb2492f341468d85ad0f3145287ace
Source dataset
uspto-grants-1998_08
Patent number
US05792557

Reaction notes

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