反応 #88802

反応方程式

Water

Diethylaniline

3-(1-hydroxyethyl)benzamide

Thionyl chloride

→

title compound

収率 75.0%

3-(1-Chloroethyl)benzamide

収率 75.0%

溶媒

DCM

反応条件

後処理

1. 1
   温度the reaction mixture was cooled with an ice-bath
2. 2
   その他was put in the refrigerator overnight
3. 3
   抽出the reaction mixture was extracted twice with DCM
4. 4
   洗浄washed with a 10% HCl solution
5. 5
   workup.ADDITIONtreated with brine
6. 6
   乾燥dried (MgSO4)
7. 7
   ろ過filtered
8. 8
   その他evaporated to dryness
9. 9
   その他The crude product was recrystallized from diethylether/hexane

実験手順

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.

出典