4-Aminobiphenyl → HCID 19751600, compound

HRID 1708846Notes

Reaction equation

HRID 1708846 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[Cl:14][C:15]1[CH:16]=[C:17](I)[CH:18]=[CH:19][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.[Cu]>[Cl:14][C:15]1[CH:16]=[C:17]([N:1]([C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:14])[CH:20]=2)[C:2]2[CH:3]=[CH:4][C:5]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[CH:6][CH:7]=2)[CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 71024-AminobiphenylHCID 11430Potassium CarbonateHCID 122691-Chloro-3-iodobenzene

Product 1

HCID 19751600HCID 19751600, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 5.3 grams of 4-aminobiphenyl, 25.0 grams of m-chloroiodobenzene and 16.5 grams of potassium carbonate in 150 milliliters of dimethyl sulfoxide was mechanically stirred and heated to 110° C. in a round-bottomed flask fitted with a reflux condenser under a nitrogen atmosphere. Subsequently, 9.5 grams of copper bronze powder was added, and the temperature of the reaction mixture was raised to 170° C. After 48 hours, the reaction mixture was filtered while still hot, and the filtrate was evaporated under reduced pressure to provide a viscous oil. Purification by column chromatography on neutral alumina using a mixture of methylene chloride and hexane (1:10) as the eluent afforded 7.9 grams of analytically pure bis(m-chlorophenyl)-4-biphenylylamine.

Workup

  1. customfitted with a reflux condenser under a nitrogen atmosphere
  2. temperaturethe temperature of the reaction mixture was raised to 170° C
  3. filtrationthe reaction mixture was filtered while still hot, and the filtrate
  4. customwas evaporated under reduced pressure
  5. customto provide a viscous oil
  6. customPurification by column chromatography on neutral alumina using
  7. additiona mixture of methylene chloride and hexane (1:10) as the eluent

Sources & evidence

ORD record
ord-97d35c53ad284e6d9814dc07d59e5bbe
Source dataset
uspto-grants-1990_08
Patent number
US04946754

Reaction notes

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