Reaktion #76082

Reaktionsgleichung

1-p-tolylcyclopropanecarboxylic acid

thionyl chloride

1-heptylamine

N,N-diisopropylethylamine

HCl

→

1-p-tolyl-cyclopropanecarboxylic acid heptylamide

Ausbeute 64.0%

Lösungsmittel

chloroform

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto reflux
2. 2
   Einengenconcentrated
3. 3
   Sonstigeto give a yellow oil
4. 4
   Temperaturcooled to 0° C
5. 5
   TemperaturThe mixture was warmed to room temperature
6. 6
   workup.STIRRINGto stir for 30 minutes
7. 7
   Sonstigethe aqueous layer was isolated
8. 8
   Extraktionextracted with dichloromethane (3×)
9. 9
   Waschenwashed with 2N HCl (1×), brine (1×)
10. 10
    Trocknendried over anhydrous sodium sulfate
11. 11
    Einengenconcentrated to a yellow oil which
12. 12
    SonstigeThe solid was crystallized from hexanes

Vorschrift

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%).

Quelle