N-benzyl-N-(cyanomethyl)nitrous amide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1.2 ml 7.5N aq. HCl was stirred (at 0° C.) into a mixture of 0.94 g benzyl amine and 0.58 g of potassium cyanide in 2 ml of water. 0.7 g formaldehyde was then added dropwise into the mixture. The resulting mixture was stirred at room temperature for 2 hours and then cooled to 0° C. A solution of 0.62 g sodium nitrite in 1 ml water was added slowly dropwise to the mixture followed by the addition of 1.2 ml 7.5N HCl aq. solution while cooling. The mixture was stirred at room temperature for 1 hour. Ether was used to extract the resulting mixture three times. The combined ether solution was dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure. N-nitroso-benzylaminoacetonitrile (see reaction scheme) was obtained as a yellow oil. The nitroso intermediate was then treated with 500 ml HCl ethereal solution (2.0 M) and stirred for 30 minutes at room temperature. White precipitate was obtained and recrystalized with 2-propanol, resulting in a white crystal. 2.84 g of the 3-benzyl-sydnonimine hydrochloride thus produced was dissolved in 25 ml of water. To the solution was added 1.34 g sodium bicarbonate at 0° C. 2.45 ml of phenyl isocyanate was then added dropwise to the mixture and stirred at 0° C. for 4 hours to the resulting mixture was added 10 ml of ether to help the yellow crystal precipitate. Methanol was used as solvent for recrystalization. The desired product was obtained as yellow crystal. cooled to 0° C while cooling The mixture was stirred at room temperature for 1 hour to extract the resulting mixture three times The combined ether solution was dried with anhydrous sodium sulfate The solvent was removed under reduced pressure