Iodobenzene → 3-methyl-N,N-diphenylaniline

HRID 35014Notes

Reaction equation

HRID 35014 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:10]=1>[Cu]>[CH3:8][C:9]1[CH:10]=[C:11]([N:15]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 11575IodobenzeneHCID 14569N-(3-Methylphenyl)aniline

Product 1

HCID 110864773-methyl-N,N-diphenylanilineYield 75%

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

The same equipment and conditions as in example I were employed with the following charge: 20.4 grams (0.1 mole) iodobenzene, 27.5 grams (0.15 mole) 3-methyldiphenylamine, 15.0 grams copper powder and 30.0 milliliters of Soltrol® 170. The above-identified intended product was obtained as colorless crystals having a melting point of 69°-70° C. Yield 75%.

Workup

  1. additionfollowing charge
  2. customThe above-identified intended product was obtained as colorless crystals

Sources & evidence

ORD record
ord-b130051439054dada6006afe8ea910ee
Source dataset
uspto-grants-1988_08
Patent number
US04764625

Reaction notes

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