Ethyl 2-amino-2-cyanoacetate → Ethyl 2-cyano-2-formamidoacetate

Participants

Reaction Steps

To ethyl 2-amino-2-cyanoacetate (800 mg, 6.24 mmol) in dichloromethane (5 mL) was added cyanomethyl formate (531 mg, 6.24 mmol) in dichloromethane (5 mL) dropwise at 0° C. The reaction was warmed up to room temperature for twelve hours. The reaction was concentrated and purified by silica gel chromatography to give an oil of ethyl 2-cyano-2-formamidoacetate (500 mg). NMR spectrum shows a mixture of starting material and desired product in a 1:1 ratio. The product was dissolved in methylene chloride (10 mL). To this solution was added cyanomethyl formate (797 mg, 9.37 mmol) and the reaction was stirred for twelve more hours. The reaction was concentrated and purified with silica gel chromatography to give an oil of ethyl 2-cyano-2-formamidoacetate (460 mg). 1H NMR (400 MHz, CDCl3) δ 8.30 (s, 1H), 6.61 (s, 1H), 5.55 (d, 2H), 4.36 (q, 2H), 1.35 (t, 3H).

Provenance & Evidence