Ethanolamine → N,N'-bis(2-hydroxyethyl)-trans-2-dodecenediamide

Participants

Reaction Conditions

Reaction Steps

A mixture of traumatic acid (4.57 g; 20 mmol) and triethylamine (4.26 g; 42 mmol) in anhydrous THF (150 ml) allowed to stir at -10° C., was dropwide added, over a period of 30 min, with a solution of isobutylchloroformate (5.74 g; 42 mmol) in THF (50 ml). The mixture was stirred at -10° C. for 2 hrs and at 0° C. for additional 15 hrs and added dropwise, over a period of 30 min, with ethanolamine (3.5 g). After stirring for additional 6 hrs at 0° C., the resulting suspension was filtered. The filtrate was discarded and the solid was dried under vacuum. The crude product obtained was crystallized from water (100 ml). The crystalline fraction was separated by filtration, washed three times with water (20 ml) and finally dried in high vacuo.

Provenance & Evidence