Cyanoacetamide → HCID 178429416, compound

Participants

Reaction Steps

Cyanoacetamide (8, 34 g, 0.40 mol) and ethyl acetoacetate (9, 52 g, 0.40 mol) were dissolved in methanol (250 mL) at room temperature, a solution of potassium hydroxide (28 g, 0.42 mol) in methanol (200 mL) was slowly added, and the resulting mixture was heated to reflux for 12 h. The reaction mixture was cooled to room temperature and the white amorphous precipitate was filtered and washed with methanol (2×50 mL). The solid product was redissolved in hot water. The solution was carefully acidified and the off-white precipitate was allowed to form. The precipitate was filtered and washed with water and methanol to yield 110 (46 g, 75%): mp>300° C. (dec) [lit. (J. Org. Chem. 1960, 25, 560-564.) mp 315-320° C. (dec)]. 1H NMR (300 MHz, DMSO-d6) δ 5.58 (s, 1H), 2.22 (s, 3H).

Provenance & Evidence