Cyanamide → HCID 178422937, compound

Participants

Reaction Steps

To 210 mg. of potassium metal dissolved in 10 ml. of absolute ethanol was added a suspension of 1.46 (4.8 mmoles) of 2-methyl-4-acetylpyridine oxime tosylate in 10 ml. of dry ethanol, and the mixture allowed to stir at room temperature for one hour. Ether (200 ml.) was added, the potassium tosylate filtered, and the filtrate extracted with (3×20 ml.) 1 N hydrochloric acid. The combined acid extracts were concentrated to a yellow solid, which was then dissolved in 30 ml. of water. Cyanamide (600 mg., 14.2 mmoles) was dissolved in the aqueous solution and the pH adjusted to 4.5 by the addition of 2 N sodium hydroxide. The solution was heated on a steam bath for one hour, cooled in an ice bath and made basic with concentrated ammonium hydroxide. The mixture was concentrated, and the residue triturated with 15 ml. of ethanol. The solids were filtered and the filtrate was treated with ether. The resulting precipitate was filtered and dried in vacuo, 755 mg. (90%), m.p. 226°-228° C.

Provenance & Evidence