Benzene → [1,1'-Biphenyl]-4,4'-diamine, N4,N4'-bis(3-methylphenyl)-N4,N4'-diphenyl-

HRID 67788

Reaction equation

HRID 67788 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][C:17]([NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:16][CH:15]=3)=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[C:28]1[CH:29]=[C:30]([CH3:34])[CH:31]=[CH:32][CH:33]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:41]S(C)=O.[CH:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>[Cu]>[C:21]1([N:20]([C:32]2[CH:33]=[CH:28][CH:29]=[C:30]([CH3:34])[CH:31]=2)[C:17]2[CH:18]=[CH:19][C:14]([C:11]3[CH:12]=[CH:13][C:8]([N:7]([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)[C:1]4[CH:6]=[CH:5][CH:4]=[C:3]([CH3:41])[CH:2]=4)=[CH:9][CH:10]=3)=[CH:15][CH:16]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 5

HCID 241BenzeneHCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 122683-IodotolueneHCID 68280N,N'-Diphenylbenzidine

Product 1

HCID 103315[1,1'-Biphenyl]-4,4'-diamine, N4,N4'-bis(3-methylphenyl)-N4,N4'-diphenyl-

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

In a 5000 milliliter, round bottom, 3 necked flask fitted with a mechanical stirrer and blanketed with argon, is placed 336 grams (1 mole) of N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine, 550 grams (2.5 moles) of m-iodotoluene, 550 grams (4 moles) potassium carbonate (anhydrous) and 50 grams of copper bronze catalyst and 1500 ml dimethylsulfoxide (anhydrous). The heterogeneous mixture is refluxed for 6 days. The mixture is allowed to cool. 2000 ml of benzene is added. The dark slurry is then filtered. The filtrate is extracted 4 times with water. Then the filtrate is dried with magnesium sulfate and filtered. The benzene is taken off under reduced pressure. The black product is column chromatographed using Woelm neutral alumina. Colorless crystals of the product are obtained by recrystallizing the product from n-octane. The melting point is 167°-169° C. The yield is 360 grams (65%).

Workup

  1. customIn a 5000 milliliter, round bottom, 3 necked flask fitted with a mechanical stirrer
  2. temperatureThe heterogeneous mixture is refluxed for 6 days
  3. temperatureto cool
  4. filtrationThe dark slurry is then filtered
  5. extractionThe filtrate is extracted 4 times with water
  6. dry with materialThen the filtrate is dried with magnesium sulfate
  7. filtrationfiltered
  8. customchromatographed
  9. customColorless crystals of the product are obtained
  10. customby recrystallizing the product from n-octane

Sources & evidence

ORD record
ord-86a6dc0eacb141b18be93852b04c1774
Source dataset
uspto-grants-1982_08
Patent number
US04346158

Linked notes

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