Nitrobenzene → HCID 21910026, compound

HRID 2268705Notes

Reaction equation

HRID 2268705 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[CH:7]=[CH:8][CH:9]=[C:10]4[C:21]=3[C:14]([C:15]3[C:20]=2[C:19]=1[CH:18]=[CH:17][CH:16]=3)=[CH:13][CH:12]=[CH:11]4.[C:22]1([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].[N+](C1C=CC=CC=1)([O-])=O>[Cu]>[C:29]1([N:28]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:2]2[CH:3]=[CH:4][C:5]3[C:6]4[CH:7]=[CH:8][CH:9]=[C:10]5[C:21]=4[C:14]([C:15]4[C:20]=3[C:19]=2[CH:18]=[CH:17][CH:16]=4)=[CH:13][CH:12]=[CH:11]5)[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

6

Reactant 4

HCID 7416NitrobenzeneHCID 11430Potassium CarbonateHCID 11487DiphenylamineHCID 118097033-bromoperylene

Product 1

HCID 21910026HCID 21910026, compound

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

The following compounds were introduced into a vessel: (a) 3-bromoperylene; (b) diphenylamine; (c) potassium carbonate; (d) copper power; and (e) nitrobenzene. Then, the mixture was stirred at 200 degrees centigrade for 40 hours. After reaction has finished, nitrobenzene was removed under a reduced pressure. Then, chloroform was added to the mixture, and filtered for removing inorganic materials. A filtrate was condensed, and then, impurities were removed by silica gel column chromatography employing ligroin. As a result, there was obtained a target material, 3-diphenylaminoperylene.

Workup

  1. additionThe following compounds were introduced into a vessel
  2. customAfter reaction
  3. customnitrobenzene was removed under a reduced pressure
  4. additionThen, chloroform was added to the mixture
  5. filtrationfiltered
  6. customfor removing inorganic materials
  7. customcondensed
  8. customimpurities were removed by silica gel column chromatography

Sources & evidence

ORD record
ord-35a9f7b1f37348d89634e8b97947046b
Source dataset
uspto-grants-2001_12
Patent number
US06329083B1

Reaction notes

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