Acetanilide → N-(4'-iodobiphenylyl)acetanilide

HRID 600116Notes

Reaction equation

HRID 600116 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+].CCCCCCCCCCCC>[Cu]>[I:24][C:21]1[CH:22]=[CH:23][C:18]([C:15]2[CH:16]=[CH:17][CH:12]=[CH:13][C:14]=2[N:4]([C:1](=[O:3])[CH3:2])[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 904AcetanilideHCID 8182DodecaneHCID 11430Potassium CarbonateHCID 763484,4'-Diiodo-1,1'-biphenyl

Product 1

HCID 23140821N-(4'-iodobiphenylyl)acetanilideYield 64.9%

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

There were mixed 20.3 g (0.15 mole) of acetanilide, 73.1 g (0.18 mole) of 4,4′-diiodobiphenyl, 22.1 g (0.16 mole) of anhydrous potassium carbonate, 2.16 g (0.034 mole) of copper powder and 35 ml of n-dodecane, followed by reaction at 190 to 205° C. for 10 hours. The reaction product was extracted with 200 ml of toluene, and the insoluble matter was removed by filtration. Then, the filtrate was concentrated to dryness. The resulting solid matter was purified by column chromatography (carrier: silica gel, eluate: toluene/ethyl acetate=6/1) to obtain 40.2 g (yield: 64.8%) of N-(4′-iodobiphenylyl)acetanilide. The melting point was 135.0 to 136.0° C.

Workup

  1. customfollowed by reaction at 190 to 205° C. for 10 hours
  2. extractionThe reaction product was extracted with 200 ml of toluene
  3. customthe insoluble matter was removed by filtration
  4. concentrationThen, the filtrate was concentrated to dryness
  5. customThe resulting solid matter was purified by column chromatography (carrier: silica gel, eluate: toluene/ethyl acetate=6/1)

Sources & evidence

ORD record
ord-2828f1bfc8204a1cb64c33bceacd85d3
Source dataset
uspto-grants-2011_03
Patent number
US07897816B2

Reaction notes

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