Ethylenediamine → HCID 59001674, compound

Participants

Reaction Conditions

Reaction Steps

To a 500 mL, three-necked round bottom flask (fitted with a reflux condenser, addition funnel, and stir bar) was added 10-undecenoyl chloride (32.2 mL, 30.4 g, 0.150 mol) and tetrahydrofuran (THF) (200 mL). To the addition funnel was added ethylenediamine (4.51 g, 0.075 mol), triethylamine (42 mL, 30.5 g, 0.300 mol), and THF (75 mL). The amine solution was added dropwise to the acid chloride solution over one hour, yielding a white precipitate. On completion of addition, the reaction mixture was stirred at 25° C. for one hour. The reaction mixture was then filtered to remove precipitated solids. The precipitated solids were added to water (250 mL) and stirred. The insoluble solid was collected via filtration, then air dried. The crude product was recrystallized from a mixture of acetone (500 mL) and water (20 mL) to produce a white solid which was dried in vacuo (that is, under vacuum) at 25° C. for 6 hours. The thus obtained compound is represented by formula (8) shown below. Yield: 10 g (34%). Melting point (M.P.): 146-148° C. 1H and 13C NMR analyses were consistent with the structure of formula (8).

Provenance & Evidence