Ethyl 3-ethoxy-3-iminopropionate hydrochloride

Chemical Properties

White crystalline powder

Uses

Ethyl 3-ethoxy-3-iminopropionate hydrochloride is an intermediate for dacarbamate and acarmine.

Synthesis

Ethyl cyanoacetate (30 mL, 281 mmol) was dissolved with anhydrous ethanol (18.1 mL, 278 mmol) in anhydrous ether (28.1 mL) at 0°C and stirred to form a homogeneous solution. Dry hydrogen chloride gas was passed into the solution until saturation. Subsequently, the reaction mixture was warmed up to 22°C with continuous stirring for 20 hours. Upon completion of the reaction, the solvent was removed by concentration under reduced pressure to afford ethyl 3-ethoxy-3-iminopropionate hydrochloride (54.4 g, 99% yield). The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 4.73 (q, J = 7.1 Hz, 2H); 4.24 (q, J = 7.2 Hz, 2H); 3.89 (s, 2H); 1.51 (t, J = 7.0 Hz, 3H); 1.30 (t, J = 7.2 Hz, 3H) ppm.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 23, p. 7207 - 7213
[2] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 7, p. 3046 - 3049
[3] Heterocycles, 1996, vol. 43, # 9, p. 1981 - 1989
[4] Tetrahedron, 2009, vol. 65, # 4, p. 757 - 764
[5] Patent: WO2006/7700, 2006, A1. Location in patent: Page/Page column 66-67