Dodecane → N,N'-diphenyl-N,N'-di-p-tolyl-4,4''-diamino-p-terphenyl

HRID 1714719Notes

Reaction equation

HRID 1714719 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][C:31](I)=[CH:30][CH:29]=3)=[CH:24][CH:23]=2)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].CCCCC[CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52]>[Cu]>[C:1]1([N:7]([C:8]2[CH:9]=[CH:10][C:11]([CH3:14])=[CH:12][CH:13]=2)[C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][C:25]([C:28]4[CH:33]=[CH:32][C:31]([N:7]([C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)[C:50]5[CH:49]=[CH:48][C:47]([CH3:46])=[CH:52][CH:51]=5)=[CH:30][CH:29]=4)=[CH:24][CH:23]=3)=[CH:18][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 8182DodecaneHCID 11430Potassium CarbonateHCID 12109N-Phenyl-p-toluidineHCID 35635834,4''-Diiodo-p-terphenyl

Product 1

HCID 14008244N,N'-diphenyl-N,N'-di-p-tolyl-4,4''-diamino-p-terphenylYield 76.4%

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Conditions

Temperature
205 °C

Procedure

Phenyl-p-tolylamine (11.5 g (0.063 mol)), 14.5 g (0.030 mol) of 4,4″-diiodo-p-terphenyl, 5.0 g (0.036 mol) of anhydrous potassium carbonate, 0.38 g (0.006 mol) of copper powder and 15 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 400 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=1:4) to obtain 13.6 g of N,N′-diphenyl-N,N′-di-p-tolyl-4,4″-diamino-p-terphenyl (compound No. 17) (yield: 76.4%, melting point: 167.2 to 168.2° C.)

Workup

  1. additionwhile introducing nitrogen gas
  2. customAfter the termination of the reaction
  3. extractionthe reaction product was extracted with 400 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=1:4)

Sources & evidence

ORD record
ord-a31a08f682b9475c8f5c32cb9b6500bc
Source dataset
uspto-grants-2010_09
Patent number
US07799492B2

Reaction notes

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