Methanesulfonic Acid → 1-(2-Mercaptoethyl)-2,6-dimethylpyridinium methanesulfonate

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,6-dimethylpyridine (19.2 mL, 0.165 mol) and methanesulfonic acid (3.27 mL, 0.050 mol) was stirred for 15 min, treated with ethylene sulfide (4.17 mL, 0.070 mol) and stirred at 100° C. for 42 h under a nitrogen atmosphere. After cooling to 25° C., the reaction mixture was diluted with ether (45 mL) and water (30 mL). The two layers were separated and the organic layer was extracted with water (2×5 mL). The aqueous layers were combined, filtered through a Celite pad, washed with ether (2×15 mL), pumped to remove the traces of organic solvents and poured on top of a column (3.0×12 cm) of μ-bondapak C-18. Elution with 3% acetonitrile 97% water mixture gave after lyophylization of the appropriate fractions 2.5 g of the impure title compound as a syrup. It was repurified by hplc (μ-bondapak C-18) to give 0.90 g (7%) of the title compound. ir (film) νmax : 2520 (SH), 1640 and 1625 (pyridinium), 1585, 1490, 1200 cm-1 (sulfonate), 1Hmr (DMSO-d6 +D2O) δ: 2.36 (3H, s, CH3SO3-), 4.62 (2H, m, CH2N+), 7.74 (2H, m, Hm of pyridinium), 8.24 (1H, m, Hp of pyridinium), uv (H2O) max : 272 (4080)mμ.

Provenance & Evidence