반응 #88802

반응 방정식

Water

Diethylaniline

3-(1-hydroxyethyl)benzamide

Thionyl chloride

→

title compound

수율 75.0%

3-(1-Chloroethyl)benzamide

수율 75.0%

용매

DCM

반응 조건

후처리

1. 1
   온도the reaction mixture was cooled with an ice-bath
2. 2
   기타was put in the refrigerator overnight
3. 3
   추출the reaction mixture was extracted twice with DCM
4. 4
   세척washed with a 10% HCl solution
5. 5
   workup.ADDITIONtreated with brine
6. 6
   건조dried (MgSO4)
7. 7
   여과filtered
8. 8
   기타evaporated to dryness
9. 9
   기타The crude product was recrystallized from diethylether/hexane

실험 절차

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.

출처