Реакция #1747829

Уравнение реакции

NaOH

n-propylamine

3-(4-methoxyphenyl)-propionic acid

thionylchloride

→

amide

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

Растворители

dichloromethane

dichloromethane

Условия реакции

Обработка

1. 1
   ДругоеThe volatiles were evaporated
2. 2
   workup.DISSOLUTIONthe resulting oil was dissolved in dichloromethane (100 mL)
3. 3
   Другоеwere separated
4. 4
   Экстракцияthe aqueous layer was extracted with dichloromethane (3×50 mL)
5. 5
   ПромывкаThe combined organic layers were washed with water (50 mL) and brine (50 mL)
6. 6
   Сушкаwas dried over MgSO4
7. 7
   ДругоеEvaporation of the solvent

Методика

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.

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