Water → Ethyl 7-{[4-(acetyloxy)nonyl](cyano)amino}heptanoate

Participants

Reaction Steps

Sodium hydride (57%, in mineral oil) (0.48 g., 0.01 mole) is washed twice with benzene then suspended in benzene (50 ml.) and dimethylformamide (50 ml.). Ethyl 7-cyanamidoheptanoate (1.98 g. 0.01 mole) (Example N, Step 2) is added and the suspension heated on the steam bath for 15 minutes. The reaction mixture is cooled to room temperature, 1-chloro-4-acetoxynonane (2.6 g., 0.01 mole) (Example A, Step 3) is added and then the reaction is heated on the steam bath for 2 hours then stirred 18 hours at room temperature. The reaction is poured into water (300 ml.) and extracted with benzene (3 × 100 ml.). The benzene is washed with brine then dried over sodium sulfate. Removal of the solvent yields an oil which is purified by silica gel chromatography, elution solvent 3% methanol in chloroform, evaporation of the appropriate fraction affords ethyl 7-[N-(4-acetoxynonyl) cyanamido]-heptanoate. The yield is 3.2 g. (83 %).

Provenance & Evidence