Potassium Carbonate → 4'-Iodo-N,N-diphenyl[1,1'-biphenyl]-4-amine

HRID 725745Notes

Reaction equation

HRID 725745 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][C:24]([I:27])=[CH:23][CH:22]=2)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>[Cu].[N+](C1C=CC=CC=1)([O-])=O>[I:27][C:24]1[CH:25]=[CH:26][C:21]([C:18]2[CH:19]=[CH:20][C:15]([N:7]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:16][CH:17]=2)=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11487DiphenylamineHCID 763484,4'-Diiodo-1,1'-biphenyl

Product 1

HCID 218488984'-Iodo-N,N-diphenyl[1,1'-biphenyl]-4-amineYield 54.1%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7416NitrobenzeneSolvent

Procedure

20.3 g (0.12 mol) of diphenylamine, 60.9 g (0.15 mol) of 4,4'-diiodobiphenyl, 19.3 g (0.14 mol) of anhydrous potassium carbonate, 1.52 g (0.024 mol) of copper powder, and 20 ml of nitrobenzene were mixed. The reaction mixture was then allowed to undergo reaction at a temperature of 190° C. to 205° C. for 21 hours. The reaction product was then extracted with 200 ml of toluene. The insoluble contents were removed by filtration. The filtrate was then concentrated to dryness. The concentrate was then purified by column chromatography (carrier: silica gel; elute: 1/3 mixture of toluene and n-hexane) to obtain 29.0 g (yield: 54.1%) of N-(4'-iodo-4-biphenylyl)-N,N-diphenylamine. The melting point of the product was from 139.5° C. to 140.5° C.

Workup

  1. customreaction at a temperature of 190° C. to 205° C. for 21 hours
  2. extractionThe reaction product was then extracted with 200 ml of toluene
  3. customThe insoluble contents were removed by filtration
  4. concentrationThe filtrate was then concentrated to dryness
  5. customThe concentrate was then purified by column chromatography (carrier: silica gel; elute: 1/3 mixture of toluene and n-hexane)

Sources & evidence

ORD record
ord-7191240293ec447788a68f321a053df9
Source dataset
uspto-grants-1998_01
Patent number
US05707747

Reaction notes

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