Hydrochloric Acid → HCID 59356299, compound

Participants

Reaction Steps

3-Mercaptopropionic acid (5.3 g, 0.05 mol) was added within 10 minutes to a stirring suspension of potassium carbonate (7.0 g, 0.051 mol) in acetonitrile (40 mL) at room temperature. The reaction mixture was added carbon disulfide (3.8 g, 0.05 mol). The resulting yellow mixture was kept stirring for two hours and then added chloroacetonitrile (3.78 g, 0.05 mol). The resulting mixture was allowed to stir at room temperature for further one hour. Water (50 mL) was added, the yellow aqueous solution was acidified with dilute hydrochloric acid until pH˜2 and extracted with diethyl ether (50 mL×2). The organic layer was dried over anhydrous magnesium sulfate. After removal of solvent, the product cyanomethyl carboxyethyl trithiocarbonate was obtained as a yellow solid (6.4 g, 58% yield) after column chromatography (silica-gel; ethyl acetate: n-hexane 3:7 as solvent). 1H NMR (CDCl3) δ 2.85 (t, 2H, HOOCCH2); 3.65 (t, 2H, CH2S); 4.15 (s, 2H, NCCH2S), 8.20 (br s, 1H, COOH). 13C NMR (CDCl3) δ 21.5, 31.7, 32.5, 114.6, 176.9, 218.3.

Provenance & Evidence