Reacción #2850

Ecuación de reacción

4-amino-3-methyl benzonitrile

benzophenone

p-toluenesulfonic acid

→

title compound

Rendimiento 90.3%

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

Rendimiento 90.3%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction vessel is fitted with a Dean-Stark trap
2. 2
   Temperaturathe solution is heated
3. 3
   Temperaturaat reflux
4. 4
   Temperaturathe solution is cooled to ambient temperatures
5. 5
   ConcentraciónThe solution is concentrated
6. 6
   OtroThe crude material is purified by column chromatography
7. 7
   Lavadoeluting with a gradient of 3% EtOAc/hexanes to 10% EtOAc/hexanes

Procedimiento

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.

Fuente