Acetanilide → N-(4'-iodo-4-biphenylyl)acetanilide

HRID 1684430Notes

Reaction equation

HRID 1684430 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:3])[CH3:2].I[C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([I:24])=[CH:20][CH:19]=2)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].[N+](C1C=CC=CC=1)([O-])=O>[Cu]>[I:24][C:21]1[CH:22]=[CH:23][C:18]([C:15]2[CH:16]=[CH:17][C:12]([N:4]([C:1](=[O:3])[CH3:2])[C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)=[CH:13][CH:14]=2)=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 904AcetanilideHCID 7416NitrobenzeneHCID 11430Potassium CarbonateHCID 763484,4'-Diiodo-1,1'-biphenyl

Product 1

HCID 19708507N-(4'-iodo-4-biphenylyl)acetanilideYield 64.9%

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

20.3 g (0.15 mol) of acetanilide, 73.1 g (0.18 mol) of 4,4'-diiodobiphenyl, 22.1 g (0.16 mol) of anhydrous potassium carbonate, 2.16 g (0.034 mol) of copper powder, and 35 ml of nitrobenzene were mixed. The reaction mixture was then allowed to undergo reaction at a temperature of 190° C. to 205° C. for 10 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: 6/1 mixture of toluene and ethyl acetate) to obtain 40.2 g (yield: 64.8%) of N-(4'-iodo-4-biphenylyl)acetanilide. The melting point of the product was from 135.0° C. to 136.0° C.

Workup

  1. customreaction at a temperature of 190° C. to 205° C. for 10 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: 6/1 mixture of toluene and ethyl acetate)

Sources & evidence

ORD record
ord-f00466a1a36341dc936d7e92004c71b4
Source dataset
uspto-grants-1997_06
Patent number
US05639914

Reaction notes

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