Water → HCID 86734144, compound

Participants

Reaction Steps

A stirred suspension of sodium hydride (57% in mineral oil) (5.0 g., excess) in a solvent mixture of benzene (75 ml.) and dimethylformide (75 ml.) is treated, over 30 minutes, with 4-acetoxynonylcyanamide (22.6 g., 0.1 mole) (Example O, Step 5) dissolved in benzene (20 ml.). Stirring is continued for one hour. Then, ethyl 7-bromo-2-methylheptanoate (Example L, Step 4) (25.3 g., 0.1 mole) is added dropwise, and the reaction is heated on the steam bath for 3.5 hours. The cooled reaction is poured into water (400 ml.) and extracted with ethyl acetate (2 × 200 ml.). The organic fractions are combined, washed with brine, then dried over sodium sulfate. The solvent is removed in vacuo to give ethyl 7-[N-(4-acetoxynonyl)cyanamido]-2-methylheptanoate as a pale yellow liquid.

Provenance & Evidence