Nitrobenzene → HCID 19708508, compound

HRID 725737Notes

Reaction equation

HRID 725737 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:14][CH:13]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].I[C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][C:32](I)=[CH:31][CH:30]=2)=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+].[N+:42]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)([O-])=O>[Cu]>[C:18]([C:15]1[CH:14]=[CH:13][C:12]([N:11]([C:8]2[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=2)[C:23]2[CH:28]=[CH:27][C:26]([C:29]3[CH:34]=[CH:33][C:32]([N:42]([C:8]4[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:6][CH:7]=4)[C:45]4[CH:50]=[CH:49][C:48]([C:15]([CH3:18])([CH3:16])[CH3:14])=[CH:47][CH:46]=4)=[CH:31][CH:30]=3)=[CH:25][CH:24]=2)=[CH:17][CH:16]=1)([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 7416NitrobenzeneHCID 11430Potassium CarbonateHCID 763484,4'-Diiodo-1,1'-biphenylHCID 458684Bis(4-tert-butylphenyl)amine

Product 1

HCID 19708508HCID 19708508, compoundYield 31.7%

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

13.4 g (0.048 mol) of 4,4'-ditertiarybutyl-N,N-diphenylamine, 7.7 g (0.019 mol) of 4,4'-diiodobiphenyl, 7.7 g (0.056 mol) of anhydrous potassium carbonate, 0.53 g (0.008 mol) of copper powder, and 5 ml of nitrobenzene were mixed. The reaction mixture was then allowed to undergo reaction at a temperature of 200° to 215° C. for 4 hours. The reaction product was then extracted with 100 ml of THF. The insoluble contents were removed by filtration. The filtrate was then concentrated to obtain a crystal. The crude crystal thus obtained was then purified by column chromatography (carrier: silica gel; elute: 1/2 mixture of toluene and n-hexane) to obtain 4.3 g (yield: 31.7%) of N,N,N',N'-tetrakis(p-tertiarybutylphenyl)benzidine. The melting point of the product was from 402.0° C. to 403.0° C.

Workup

  1. customreaction at a temperature of 200° to 215° C. for 4 hours
  2. extractionThe reaction product was then extracted with 100 ml of THF
  3. customThe insoluble contents were removed by filtration
  4. concentrationThe filtrate was then concentrated
  5. customto obtain a crystal
  6. customThe crude crystal thus obtained
  7. customwas then purified by column chromatography (carrier: silica gel; elute: 1/2 mixture of toluene and n-hexane)

Sources & evidence

ORD record
ord-65c147aea2784dddbd480effef8028c7
Source dataset
uspto-grants-1998_01
Patent number
US05707747

Reaction notes

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