Methanesulfonic Acid → HCID 20159242, compound

Participants

Reaction Conditions

Reaction Steps

To precooled (5° C.) 3-methoxypyridine (698 mg, 6.4 mmol) was added dropwise methanesulfonic acid (0.216 mL, 3.05 mmol) and ethylene sulfide (0.19 mL, 3.2 mmol). The mixture was then heated at 60° C. for 18 h, cooled to 20° C., diluted with water (10 mL) and washed with ether (3×10 mL). The aqueous phase was pumped under high vacuum for 15 min and poured on a C18 reverse phase column. The title compound was eluted with water. The appropriate fractions were combined and evaporated under high vacuum to give the desired thiol (61.6 mg, yield 76.3%); ir (CH2Cl2) νmax :2550 (w, SH) and 1620, 1600, 1585 cm-1 (m, aromatic); 1Hmr (DMSO d6) δ: 8.90-7.90 (4H, m, aromatic C-H), 4.72 (2H, t, J=6.6 Hz, CH2N+), 4.01 (3H, s, OCH3), 3.5-3.0 (m, hidden CH2S), 2.66 (1H, dd, J=9.6 Hz, J=7.5 Hz, SH) and 2.31 ppm (3H, s, CH3SO3).

Provenance & Evidence