Diethyl Malonate → HCID 178516640, compound

Participants

Reaction Steps

A solution of sodium ethoxide in ethanol [previously prepared by dissolving sodium (2.12 g, 92.2 mmol) in ethanol (200 mL)] was treated with diethyl malonate (6.1 mL, 40.2 mmol) with stirring at ambient temperature. A solution of cyclohexanecarboximidamide hydrochloride (5 g, 31 mmol) in ethanol (100 mL) was then added dropwise with stirring at room temperature. On completion of addition the reaction mixture was heated at reflux for 8 h and allowed to stand overnight. The reaction mixture was concentrated in vacuo, water added and the pH adjusted to pH 7-8 using 2N HCl. The resulting solid formed was filtered and washed with diethyl ether to give the title compound as a solid (5.53 g, 93%). MS (ES+) m/e=195. 1H NMR: (DMSO) 1.09-1.81 (10H, m), 2.40-2.53 (1H, m), 5.09 (1H, s), 11.61 (2H, brs).

Provenance & Evidence