Nitrobenzene → 5-[N-(4-tolyl)-N-phenylamino]acenaphthene

HRID 1953

Reaktionsgleichung

Reaktionsgleichung von HRID 1953
[C:1]1([CH3:20])[CH:6]=[CH:5][C:4]([NH:7][C:8]2[C:18]3[C:19]4[C:11]([CH2:12][CH2:13][C:14]=4[CH:15]=[CH:16][CH:17]=3)=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.I[C:22]1[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].C1(C)C=CC=CC=1>[C:1]1([CH3:20])[CH:2]=[CH:3][C:4]([N:7]([C:8]2[C:18]3[C:19]4[C:11]([CH2:12][CH2:13][C:14]=4[CH:15]=[CH:16][CH:17]=3)=[CH:10][CH:9]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:5][CH:6]=1

Komponenten

7

Edukt 4

HCID 7416NitrobenzeneHCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 196889145-[N-(4-tolyl)amino]acenaphthene2×

Produkt 1

HCID 196889135-[N-(4-tolyl)-N-phenylamino]acenaphtheneAusbeute 83,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23978CopperKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

4.66 g (0.018 mol) of the above prepared 5-[N-(4-tolyl)amino]acenaphthene was mixed with 4.99 g (0.022 mol) of iodo benzene, 0.13 g (0.002 mol) of copper powder, 2.76 g (0.02 mol) of anhydrous potassium carbonate and 5 ml of nitrobenzene, and the resultant mixture was stirred at 200° C. for 25 hours. The reaction was determined to be finished when disappearance of 5-[N-(4-tolyl)amino]acenaphthene was identified. 100 ml of toluene was added thereto to dissolve the reaction product, and the mixture was filtrated and concentrated. The concentrated material thus obtained was purified by column chromatography (carrier: silica gel, eluent: toluene/hexane=1/4) to obtain 5.06 g (yield: 83.8%, melting point: 147.0°-148.0° C.) of 5-[N-(4-tolyl)-N-phenylamino]acenaphthene.

Aufarbeitung

  1. dissolutionto dissolve the reaction product
  2. filtrationthe mixture was filtrated
  3. concentrationconcentrated
  4. customThe concentrated material thus obtained
  5. customwas purified by column chromatography (carrier: silica gel, eluent: toluene/hexane=1/4)

Quellen und Nachweise

ORD-Eintrag
ord-a22b523213134b988e3fb268968dfa76
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05728500

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