2-Cyano-N-methyl-acetamide

Uses

2-Cyano-N-methylacetamide is used in the synthesis of pyridone compounds and benzimidazoles, for various pharmaceutical application.

Synthesis

1. General procedure for the synthesis of 2-cyano-N-methylacetamide: 20 g (176.8 mmol) of ethyl cyanoacetate was added slowly and dropwise at 0 °C to a tetrahydrofuran (THF) solution of 10.9 g (353.6 mmol) of methylamine, which had been cooled to 0 °C. The reaction was completed with stirring. After the dropwise addition was completed, the reaction mixture was kept at 0 °C with continued stirring. Subsequently, the reaction mixture was stirred at room temperature overnight. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The crude product was purified by recrystallization with toluene to give 16.8 g of beige solid product in 96% yield with a melting point of 99 °C.

References

[1] Patent: US2011/251194, 2011, A1. Location in patent: Page/Page column 14
[2] Patent: US2011/124643, 2011, A1. Location in patent: Page/Page column 14
[3] Patent: US2013/178472, 2013, A1. Location in patent: Paragraph 0228
[4] Marine Drugs, 2012, vol. 10, # 6, p. 1412 - 1421
[5] Journal of Medicinal Chemistry, 2018, vol. 61, # 12, p. 5350 - 5366