Hydrochloric Acid → N-methyl-S-methyl-N'-[2-(2-dimethylaminomethylthiazol-4-ylmethylthio)ethyl]isothiourea

Participants

Reaction Steps

Two g. of 2-dimethylaminomethyl-4-(2-aminoethyl)thiomethylthiazole, 25 ml. of denatured ethanol, 0.72 ml. of concentrated hydrochloric acid and 1.16 g. of methylcarbonimidodithioic acid, dimethyl ester, were added to a flask and heated under reflux for 16 hours. The reaction mixture was then evaporated to an oily residue under vacuum, and the residue was taken up in 25 ml. of water and extracted with two 15 ml. portions of diethyl ether. The aqueous layer was cooled and 3 ml. of 50% aqueous sodium hydroxide was added. The aqueous solution was then extracted with two 20 ml. portions of diethyl ether, and the extract was evaporated to dryness under vacuum to obtain 2.0 g. of crude product, which was identified by its mass spectrum, showing a molecular ion of weight 318, and by its nuclear magnetic resonance spectrum; 'H NMR (CDCl3) δ7.07 (s, 1H), 3.87 (s, 2H), 3.75 (s, 2H), 3.42 (t, 2H), 2.75 (m, 2H) and 2.33 (s, 9H).

Provenance & Evidence