Sodium Cyanide → HCID 86735627, compound

Participants

Reaction Steps

10 Mmol (4.3 g) of 5-chloro-4'-trifluoromethylvalerophenone O-(2-aminoethyl) oxime maleate (1:1) (melting point 121.5°-122.5° C) were dissolved in 50 ml of water. 5 Ml of 50% sodium hydroxide solution at 0° C were added. Three extractions with 25 ml of CH2Cl2 were then carried out and this extract was washed with 5% sodium bicarbonate solution (1x) and water (1x). The solution was then dried on sodium sulphate and the CH2Cl2 was distilled off in vacuo. The residue was dissolved in 10 ml of dimethylsulfoxide (DMSO) and 25 mmol (1.2 g) of sodium cyanide were then added. The suspension was heated at a temperature of 50° to 70° C for 3 hours and then cooled to room temperature. Then there was diluted with 100 ml of 0.5 N sodium hydroxide solution and three extractions with 40 ml of ether were carried out. The ether extract was washed with water (1x), dried on sodium sulphate and evaporated in vacuo. The residue was purified chromatographically over silica gel with ethanol/ammonia (95:5) as an eluent. After evaporating the solvents, the residue was dissolved in absolute ethanol and acidified with ethanolic hydrochloric acid. After crystallization from ethanol/ether (1:3) the title compound having a melting point of 142°-143.5° C was obtained.

Provenance & Evidence