반응 #977780

반응 방정식

NaOH

n-propylamine

3-(4-methoxyphenyl)-propionic acid

thionylchloride

→

amide

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

용매

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   기타The volatiles were evaporated
2. 2
   workup.DISSOLUTIONthe resulting oil was dissolved in dichloromethane (100 mL)
3. 3
   기타were separated
4. 4
   추출the aqueous layer was extracted with dichloromethane (3×50 mL)
5. 5
   세척The combined organic layers were washed with water (50 mL) and brine (50 mL)
6. 6
   건조was dried over MgSO4
7. 7
   기타Evaporation of the solvent

실험 절차

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.

출처