Benzophenone → 4-(Benzhydrylidene-amino)-3-methyl-benzonitrile

HRID 2754

Reaktionsgleichung

Reaktionsgleichung von HRID 2754
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH3:10].[C:11]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:11](=[N:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH3:10])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

5

Edukt 3

HCID 3102BenzophenoneHCID 6101p-Toluenesulfonic acidHCID 70103164-Amino-3-methylbenzonitrile

Produkt 1

HCID 193509624-(Benzhydrylidene-amino)-3-methyl-benzonitrileAusbeute 90,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 4-amino-3-methyl benzonitrile (1.20 g, 9.08 mmol) in 75 mL of toluene is added benzophenone (1.74 g, 9.53 mmol) and p-toluenesulfonic acid (0.43 g, 2.1 mmol). The reaction vessel is fitted with a Dean-Stark trap and the solution is heated at reflux. After 24 h, the solution is cooled to ambient temperatures. The solution is concentrated. The crude material is purified by column chromatography eluting with a gradient of 3% EtOAc/hexanes to 10% EtOAc/hexanes. The title compound (2.43 g, 8.2 mmol) is obtained as an oil.

Aufarbeitung

  1. customThe reaction vessel is fitted with a Dean-Stark trap
  2. temperaturethe solution is heated
  3. temperatureat reflux
  4. temperaturethe solution is cooled to ambient temperatures
  5. concentrationThe solution is concentrated
  6. customThe crude material is purified by column chromatography
  7. washeluting with a gradient of 3% EtOAc/hexanes to 10% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-8506789e76894b63af6d91cbe4235510
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05731315

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