Nitrobenzene → HCID 18510026, compound

HRID 1370603Notes

Reaction equation

HRID 1370603 reaction equation
Br[C:2]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]2[C:17]3[C:22]([C:23](Br)=[C:24]4[C:29]=2[CH:28]=[CH:27][CH:26]=[CH:25]4)=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[CH:7]2.[C:31]1([NH:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(=O)([O-])[O-].[K+].[K+].[N+:50]([C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)([O-])=O>[Cu].C1(C)C=CC=CC=1>[C:38]1([N:37]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:2]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([C:16]3[C:17]4[C:22]([C:23]([N:50]([C:2]5[CH:15]=[CH:10][CH:9]=[CH:8][CH:3]=5)[C:53]5[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=5)=[C:24]5[C:29]=3[CH:28]=[CH:27][CH:26]=[CH:25]5)=[CH:21][CH:20]=[CH:19][CH:18]=4)=[C:8]3[C:3]=2[CH:4]=[CH:5][CH:6]=[CH:7]3)[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

7

Reactant 4

HCID 7416NitrobenzeneHCID 11430Potassium CarbonateHCID 11487DiphenylamineHCID 1519599910,10'-Dibromo-9,9'-bianthracene

Product 1

HCID 18510026HCID 18510026, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 1140TolueneSolvent

Procedure

In a flask were placed 35 g of 9,9′-bianthryl and 300 mL of carbon tetrachloride, and to the vigorously stirred mixture was slowly added 40 g of bromine under cooling. After addition, the mixture was slowly warmed and then refluxed for 1 hour with stirring. Carbon tetrachloride was evaporated from the reaction mixture under a reduced pressure, the residual solid was extracted with carbon tetrachloride using a Soxhlet extractor. The extract was dried and concentrated to give 42 g(yield 81%) of 10,10′-dibromo-9,9′-bianthryl. Then, in a 100 mL three-necked flask were placed 25 g of 10,10′-dibromo-9,9′-bianthryl, 20 g of diphenylamine, 17 g of potassium carbonate, 0.4 g of copper powder and 80 mL of nitrobenzene, and the mixture was stirred at 200° C. for 30 hours. After completion of the reaction, toluene was added to the mixture. The mixture was filtered to remove inorganics. Toluene and nitrobenzene were evaporated under a reduced pressure. The residue was purified by column chromatography on silica gel eluting with a 1:2 mixture of toluene and ligroin, to give 19 g(yield: 55%) of 10,10′-bis(diphenylamino)-9,9′-bianthryl.

Workup

  1. customThen, in a 100 mL three-necked flask were placed
  2. additionwas added to the mixture
  3. filtrationThe mixture was filtered
  4. customto remove inorganics
  5. customToluene and nitrobenzene were evaporated under a reduced pressure
  6. customThe residue was purified by column chromatography on silica gel eluting with a 1:2 mixture of toluene and ligroin

Sources & evidence

ORD record
ord-7c9c11d3a2e047e8a1c34644d22c5d63
Source dataset
uspto-grants-2003_06
Patent number
US06582837B1

Reaction notes

Loading…