Potassium Carbonate → N,N,N',N'-tetra-p-tolyl-4,4''-diamino-p-terphenyl

HRID 1714720Notes

Reaction equation

HRID 1714720 reaction equation
[C:1]1([CH3:15])[CH:6]=[CH:5][C:4]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.I[C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][C:26]([C:29]3[CH:34]=[CH:33][C:32](I)=[CH:31][CH:30]=3)=[CH:25][CH:24]=2)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>[Cu].CCCCCCCCCCCC>[C:11]1([CH3:14])[CH:12]=[CH:13][C:8]([N:7]([C:4]2[CH:3]=[CH:2][C:1]([CH3:15])=[CH:6][CH:5]=2)[C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:34]=[CH:33][C:32]([N:7]([C:8]5[CH:9]=[CH:10][C:11]([CH3:14])=[CH:12][CH:13]=5)[C:4]5[CH:3]=[CH:2][C:1]([CH3:15])=[CH:6][CH:5]=5)=[CH:31][CH:30]=4)=[CH:25][CH:24]=3)=[CH:19][CH:18]=2)=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 69293Benzenamine, 4-methyl-N-(4-methylphenyl)-HCID 35635834,4''-Diiodo-p-terphenyl

Product 1

HCID 59383741N,N,N',N'-tetra-p-tolyl-4,4''-diamino-p-terphenylYield 65.7%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 8182DodecaneSolvent

Conditions

Temperature
205 °C

Procedure

Di-p-tolylamine (12.8 g (0.065 mol)), 14.0 g (0.029 mol) of 4,4″-diiodo-p-terphenyl, 4.7 g (0.034 mol) of anhydrous potassium carbonate, 0.51 g (0.008 mol) of copper powder and 30 ml of n-dodecane were mixed, and heated up to 200 to 210° C. while introducing nitrogen gas, followed by stirring for 30 hours. After the termination of the reaction, the reaction product was extracted with 500 ml of toluene, and 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, eluent: toluene:hexane=1:2) to obtain 11.8 g of N,N,N′,N′-tetra-p-tolyl-4,4″-diamino-p-terphenyl (comparative compound No. 1) (yield: 65.7%, melting point: 232.5 to 233.5° C.).

Workup

  1. additionwhile introducing nitrogen gas
  2. customAfter the termination of the reaction
  3. extractionthe reaction product was extracted with 500 ml of toluene, and insoluble matter
  4. customwas removed by filtration
  5. concentrationThen, the filtrate was concentrated to dryness
  6. customThe resulting solid matter was purified by column chromatography (carrier: silica gel, eluent: toluene:hexane=1:2)

Sources & evidence

ORD record
ord-77f7f7883f024d36ba7cb18224dbbdb2
Source dataset
uspto-grants-2010_09
Patent number
US07799492B2

Reaction notes

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