Reaction #88802

Reaction equation

Water

Diethylaniline

3-(1-hydroxyethyl)benzamide

Thionyl chloride

→

title compound

Yield 75.0%

3-(1-Chloroethyl)benzamide

Yield 75.0%

Solvents

DCM

Conditions

Workup

1. 1
   Temperaturethe reaction mixture was cooled with an ice-bath
2. 2
   Otherwas put in the refrigerator overnight
3. 3
   Extractionthe reaction mixture was extracted twice with DCM
4. 4
   Washwashed with a 10% HCl solution
5. 5
   workup.ADDITIONtreated with brine
6. 6
   Dryingdried (MgSO4)
7. 7
   Filtrationfiltered
8. 8
   Otherevaporated to dryness
9. 9
   OtherThe crude product was recrystallized from diethylether/hexane

Procedure

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.

Source