Dimethyl Sulfate → 2-Bromopropionic acid N-cyano-N-methylamide

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Reaction Steps

10.5 g (0.25 mole) of cyanamide are dissolved in 250 ml of 2N potassium hydroxide solution and the solution so obtained is cooled to +10° C. At this temperature 26.5 ml (0.25 mole) of 2-bromopropionyl bromide are added dropwise and the reaction mixture is stirred for one hour at the same temperature. Then 16.8 g (0.2 mole) of sodium bicarbonate are added. 63 g (0.5 mole) of dimethylsulfate are subsequnetly added dropwise at 20° C. and the reaction mixture is stirred for 4 hours and extracted with methylene chloride. The combined organic phases are dried over sodium sulfate and concentrated by evaporation, affording as residue 27.5 g of crude product. Vacuum distillation of this crude products yields 13.6 g (28.5% of theory) of 2-bromopropionic acid N-cyano-N-methylamide with a boiling point of 45°-47° C. at 0.008 mbar.

Provenance & Evidence