Sulfuric Acid → Trimethylpyruvic acid amide

Participants

Reaction Steps

55.5 g (0.5 mole) of pivaloyl cyanide and 2 g of ammonium chloride were introduced into a 500 ml three-necked flask. The mixture was cooled to -5° to 0° C. and 100 ml of concentrated sulphuric acid was added dropwise at this temperature. 18 ml (1 mole) of water were then added dropwise, also at -5° to 0° C. The reaction mixture was subsequently stirred at -5° to 0° C. for 12 hours and was then poured onto a solution of 350 g of sodium carbonate in 600 ml of water. It was extracted twice with 300 ml of methylene chloride each time. The combined organic phases were washed with 300 ml of water, dried over sodium sulphate and concentrated by distilling off the solvent in vacuo. Recrystallization from petroleum ether gave 66 g (51.2% of theory) of trimethylpyruvic acid amide of melting point 67° to 69° C.

Provenance & Evidence