Reacción #88802

Ecuación de reacción

Water

Diethylaniline

3-(1-hydroxyethyl)benzamide

Thionyl chloride

→

title compound

Rendimiento 75.0%

3-(1-Chloroethyl)benzamide

Rendimiento 75.0%

Disolventes

DCM

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe reaction mixture was cooled with an ice-bath
2. 2
   Otrowas put in the refrigerator overnight
3. 3
   Extracciónthe reaction mixture was extracted twice with DCM
4. 4
   Lavadowashed with a 10% HCl solution
5. 5
   workup.ADDITIONtreated with brine
6. 6
   Secadodried (MgSO4)
7. 7
   Filtraciónfiltered
8. 8
   Otroevaporated to dryness
9. 9
   OtroThe crude product was recrystallized from diethylether/hexane

Procedimiento

Diethylaniline (390 μL, 2.45 mmol) was added 3-(1-hydroxyethyl)benzamide (400 mg, 2.45 mmol) slurried in DCM (20 mL) and the reaction mixture was cooled with an ice-bath. Thionyl chloride ((255 μL, 2.47 mmol) was added dropwise and the reaction was put in the refrigerator overnight. Water was added, the reaction mixture was extracted twice with DCM, washed with a 10% HCl solution, neutralized with a saturated bicarbonate solution, treated with brine, dried (MgSO4), filtered and evaporated to dryness. The crude product was recrystallized from diethylether/hexane to give 335 mg (75% yield) of the title compound as a white solid.

Fuente