N,N-dimethyl-2-Furanmethanamine → N-[2-[[[5-[(Dimethylamino)methyl]-2-furanyl]methyl]thio]ethyl]-1-methyl-3-[(methylsulphonyl)methyl]-1H-1,2,4-triazol-5-amine

Participants

Reaction Steps

Methyl 1-methyl-N-[(methylsulphonyl)acetyl]-2-(phenylmethylene)hydrazinecarboximidothioate (1.05 g) and 5-[[2-aminoethyl)thio]methyl]-N,N-dimethylfuranmethanamine (0.85 g)in acetonitrile (3 ml) were heated on a steam bath at atmospheric pressure for 5 minutes then under water vacuum for 10 minutes. The oily residue was dissolved in acetonitrile (3 ml) and the solution re-evaporated under water vacuum. The oily residue was dissolved in 2N hydrochloric acid (3 ml) and 5N hydrochloric acid (4 ml) added to the solution. The solution was heated on a steam bath for 15 minutes and after cooling to room temperature, water (10 ml) was added and the oily suspension extracted with ethyl acetate. The aqueous phase was basified with sodium carbonate and the oily suspension extracted with ethyl acetate to yield an oil (0.84 g). This was chromatographed (using solvent system D) to give the title compound (0.78 g) as an oil. T.l.c. System D, Rf 0.5.

Provenance & Evidence