Reacción #323232

Ecuación de reacción

2-methylpyridinium methanesulfonate

methanesulfonic acid

ethylene sulfide

→

title compound

Rendimiento 85.0%

1-(2-mercaptoethyl)-2-methylpyridinium methanesulfonate

Rendimiento 85.0%

Disolventes

water

2-methylpyridine

2-methylpyridine

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled to 23° C.
2. 2
   LavadoThe aqueous solution was washed with ether (6×4 mL)
3. 3
   Otroto remove traces of organic solvents
4. 4
   workup.ADDITIONpoured on top of a column (2.5×10.0 cm) of μ-bondapak C-18
5. 5
   LavadoThe column was eluted with water and lyophilization of the appropriate fractions

Procedimiento

To a suspension of 2-methylpyridinium methanesulfonate in 2-methylpyridine prepared by the addition of methanesulfonic acid (0.65 mL, 0.010 mol) to cold 2-methylpyridine (2.17 mL, 0.022 mol) was added ethylene sulfide (0.655 mL, 0.011 mol). The reaction mixture was stirred under a nitrogen atmosphere at 55° C. for 21 h, cooled to 23° C. and diluted with water (5 mL). The aqueous solution was washed with ether (6×4 mL) pumped to remove traces of organic solvents and poured on top of a column (2.5×10.0 cm) of μ-bondapak C-18. The column was eluted with water and lyophilization of the appropriate fractions gave 2.13 g (85%) of the title compound, ir (film) νmax : 2520 (SH), 1623 (pyridinium) 1574, 1512, 1485, 1412, 1195 (sulfonate), 1038 cm-1, 1Hmr (DMSO-d6 +D2O) δ: 2.37 (3H, s, CH3SO3-), 2.83 (3H, s, CH3 on pyridinium), 3.09 (2H, J=6.9 Hz, CH2S), 4.71 (2H, t, J=6.9 Hz, CH2N+), 7.93 (2H, m, Hm of pyridinium), 8.44 (1H, m, Hp of pyridinium), 8.89 (1H, m, Ho of pyridinium), uv (H2O) λmax : 266 (ε3550) m μ.

Fuente