N-Methylcyanoacetamide

1.3: N-methylcyanoacetamideVariantA stream of methylamine (gas) is passed through a solution of 30.0 g (265.2 mmol) of ethyl cyanoacetate in 220 ml of THF, for 2 h, while maintaining the temperature below 25° C. The THF is evaporated off and 25.86 g of white solid are obtained. Yield=99.4percent; Mp=100-102° C.To 10.9 g (353.6 mmol) of a solution of methylamine in THF, cooled to 0° C., are added dropwise 20 g (176.8 mmol) of ethyl cyanoacetate, and the reaction mixture is then stirred at room temperature overnight. The solvents are evaporated off under reduced pressure and the product is purified by recrystallization from toluene. 16.8 g of product are obtained in the form of a beige-coloured solid. Yield=96percent. Melting point=99° C.1.3: 2-cyano-N-methylacetamide General procedure: A mixture of ethyl cyanoacetate (1.1g, 10mmol) and amine (11mmol) was stirred at 20-25°C. After 24 h, the Precipitate will be filtered and washed with cold diethyl ether, then dried on vacuum.General procedure: To ethyl cyanoacetate (19.8 g, 175 mmol) at -10 °C was added a solution of 40percent aqueous methylamine (19.7 mL, 254 mmol) drop-wise with stirring, while maintaining the temperature below 0 °C. The mixture was stirred for an additional 1 h at 0 °C to result a white solid. The mixture was further stirred for 3 h at room temperature. Most of the residual solvents were evaporated, and the residue obtained was dissolved in ethyl acetate (200 mL). The solution was dried over anhydrous Na12.28 ml (128.44 mmol) of ethyl chloroformate are added, dropwise, to a solution, cooled to -30° C., of 10.0 g (116.38 mmol) of cyanoacetic acid at 99percent and 16.3 ml (116.9 mmol) of triethylamine in 100 ml of anhydrous THF, and the mixture is then stirred at -30° C. for 1 hour 30 minutes. 300 ml of methanol saturated with methylamine gas are then added dropwise and the mixture is then stirred at ambient temperature overnight. 12.28 ml (128.44 mmol) of ethyl chloroformate are added dropwise to a solution, cooled to -30° C., of 10.0 g (116.38 mmol) of 99percent cyanoacetic acid and 16.3 ml (116.9 mmol) of triethylamine in 100 ml of anhydrous THF and then the mixture is stirred at -30° C. for one and a half hours. 300 ml of methanol saturated with gaseous methylamine are subsequently added dropwise and then the mixture is stirred at ambient temperature overnight.

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

Molecular Weight:98.10
XLogP3:-0.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:98.048012819
Monoisotopic Mass:98.048012819
Topological Polar Surface Area:52.9
Heavy Atom Count:7
Complexity:110
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes