Reacción #83176

Ecuación de reacción

anthranilonitrile

4-[(diethoxyphosphoryl)-methyl]benzoyl chloride

→

diethyl 4-[N-(2-cyanophenyl)carbamoyl]benzyl-phosphonate

Disolventes

pyridine

dichloromethane

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooling
2. 2
   Lavadowashed with diluted hydrochloric acid
3. 3
   SecadoThe organic layer was dried over anhydrous magnesium sulfate
4. 4
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
5. 5
   OtroThe residue was recrystallized from chloroform-n-hexane

Procedimiento

A 15.7 g portion of anthranilonitrile was dissolved in 50 ml of pyridine. While the solution was stirred under ice-cooling, a solution of 40.7 g of 4-[(diethoxyphosphoryl)-methyl]benzoyl chloride in 50 ml of dry dichloromethane was added dropwise. The stirring was continued at room temperature for 12 hours, after which the reaction mixture was diluted with 200 ml of dichloromethane and washed with diluted hydrochloric acid. The organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was recrystallized from chloroform-n-hexane to provide 25.9 g of diethyl 4-[N-(2-cyanophenyl)carbamoyl]benzyl-phosphonate as colorless crystals.

Fuente