Potassium Cyanide → HCID 23458556, compound

Participants

Reaction Conditions

Reaction Steps

A cold solution of 2.4 g (34.8 millimoles) of sodium nitrite in 20 ml of water is added to a solution of 7.0 g (34.8 millimoles) of 2-(p-aminophenyl)-3,4-diaza-bicyclo[4.1.0]hept-2-en-5-one (see Example 8a) in 26 ml of concentrated hydrochloric acid and 260 ml of water whilst stirring at 0° C. The mixture is then stirred for a further 10 minutes, at 0°-5° C., after which it is neutralized with sodium carbonate at the same temperature. The resulting solution is added dropwise, whilst stirring, to a cold (0°-5° C.) solution of 3.9 g (43.5 millimoles) of copper-(I) cyanide and 7.0 g (107.5 millimoles) of potassium cyanide in 175 ml of water, covered with a layer of 85 ml of toluene. The mixture is then stirred for 30 minutes at 5° C., followed by 20 hours at room temperature. After filtering off the product and drying it under reduced pressure at 50° C., 6.6 g (90% of theory) of 2-(p-cyanophenyl)-3,4-diaza-bicyclo[4.1.0]hept-2-en-5-one are obtained as brown crystals, of melting point 265°-266° C. after recrystallization from acetonitrile.

Provenance & Evidence