Potassium Carbonate → N,N'-bisindane-5-yl-N,N'-di-p-tolyl-4,4''-diamino-p-terphenyl

HRID 1714717Notes

Reaction equation

HRID 1714717 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=3)=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.I[C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([C:31]3[CH:36]=[CH:35][C:34](I)=[CH:33][CH:32]=3)=[CH:27][CH:26]=2)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>[Cu].CCCCCCCCCCCC>[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([N:10]([C:11]3[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=3)[C:19]3[CH:24]=[CH:23][C:22]([C:25]4[CH:30]=[CH:29][C:28]([C:31]5[CH:36]=[CH:35][C:34]([N:10]([C:6]6[CH:5]=[C:4]7[C:9](=[CH:8][CH:7]=6)[CH2:1][CH2:2][CH2:3]7)[C:11]6[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=6)=[CH:33][CH:32]=5)=[CH:27][CH:26]=4)=[CH:21][CH:20]=3)=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 35635834,4''-Diiodo-p-terphenylHCID 15309875Indane-5-yl-p-tolylamine

Product 1

HCID 59383744N,N'-bisindane-5-yl-N,N'-di-p-tolyl-4,4''-diamino-p-terphenylYield 75.8%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 8182DodecaneSolvent

Conditions

Temperature
205 °C

Procedure

Indane-5-yl-p-tolylamine (18.1 g (0.081 mol)), 18.9 g (0.039 mol) of 4,4″-diiodo-p-terphenyl, 7.2 g (0.052 mol) of anhydrous potassium carbonate, 0.76 g (0.012 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 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 19.9 g of N,N′-bisindane-5-yl-N,N′-di-p-tolyl-4,4″-diamino-p-terphenyl (compound No. 1) (yield: 75.7%, melting point: 207.4 to 208.1° 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-926fe9fbabab4f358bcfa9e04355855b
Source dataset
uspto-grants-2010_09
Patent number
US07799492B2

Reaction notes

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