반응 #76082

반응 방정식

1-p-tolylcyclopropanecarboxylic acid

thionyl chloride

1-heptylamine

N,N-diisopropylethylamine

HCl

→

1-p-tolyl-cyclopropanecarboxylic acid heptylamide

수율 64.0%

용매

chloroform

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   온도to reflux
2. 2
   농축concentrated
3. 3
   기타to give a yellow oil
4. 4
   온도cooled to 0° C
5. 5
   온도The mixture was warmed to room temperature
6. 6
   workup.STIRRINGto stir for 30 minutes
7. 7
   기타the aqueous layer was isolated
8. 8
   추출extracted with dichloromethane (3×)
9. 9
   세척washed with 2N HCl (1×), brine (1×)
10. 10
    건조dried over anhydrous sodium sulfate
11. 11
    농축concentrated to a yellow oil which
12. 12
    기타The solid was crystallized from hexanes

실험 절차

To a solution of 1-p-tolylcyclopropanecarboxylic acid (5.68 grams) in chloroform (10 mL) was added thionyl chloride (17.0 mmol, 1.26 mL). The resulting mixture was brought to reflux and was allowed to stir for 3 h. The mixture was cooled to room temperature and concentrated to give a yellow oil. The oil was dissolved in dichloromethane (5 mL) and added dropwise to a solution of 1-heptylamine (6.82 mmol, 1.01 mL) and N,N-diisopropylethylamine (6.82 mmol, 1.19 mL) dissolved in dichloromethane (10 mL) cooled to 0° C. The mixture was warmed to room temperature and was allowed to stir for 30 minutes. The solution was poured over 1 N HCl, and the aqueous layer was isolated and extracted with dichloromethane (3×). The organic layers were combined, washed with 2N HCl (1×), brine (1×), dried over anhydrous sodium sulfate and concentrated to a yellow oil which solidified under high vacuum. The solid was crystallized from hexanes to give 1-p-tolyl-cyclopropanecarboxylic acid heptylamide as a white solid (1.0 g, 64%).

출처