反応 #977780

反応方程式

NaOH

n-propylamine

3-(4-methoxyphenyl)-propionic acid

thionylchloride

→

amide

3-(4-methoxyphenyl)-propionic acid n-propylamide

溶媒

dichloromethane

dichloromethane

反応条件

後処理

1. 1
   その他The volatiles were evaporated
2. 2
   workup.DISSOLUTIONthe resulting oil was dissolved in dichloromethane (100 mL)
3. 3
   その他were separated
4. 4
   抽出the aqueous layer was extracted with dichloromethane (3×50 mL)
5. 5
   洗浄The combined organic layers were washed with water (50 mL) and brine (50 mL)
6. 6
   乾燥was dried over MgSO4
7. 7
   その他Evaporation of the solvent

実験手順

3-(4-methoxyphenyl)-propionic acid (8.8 g, 49 mmol) was refluxed in dichloromethane (200 mL) with thionylchloride (6.6 mL, 90 mmol) for 1 h. The volatiles were evaporated and the resulting oil was dissolved in dichloromethane (100 mL). This was added to a vigorously stirred mixture of 5% aqueous NaOH (200 mL), dichloromethane (100 mL) and n-propylamine (3.0 mL, 71 mmol). After stirring for 1 h the layers were separated and the aqueous layer was extracted with dichloromethane (3×50 mL). The combined organic layers were washed with water (50 mL) and brine (50 mL) and was dried over MgSO4. Evaporation of the solvent gave the amide in quantitative yield (10.7 g, 49 mmol, 100%). IR (neat) cm−1 3300, 2961; 1734, 1642; MS (EI) m/z 221 (M+) Analyses were in agreement with literature data.

出典