Reaction equation
[CH3:1][S:2]([O-:5])(=[O:4])=[O:3].[CH3:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][NH+:8]=1.CS(O)(=O)=O.[CH2:18]1[S:20][CH2:19]1>CC1C=CC=CN=1.O>[CH3:1][S:2]([O-:5])(=[O:4])=[O:3].[SH:20][CH2:19][CH2:18][N+:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[CH3:6]Participants
Conditions
- Temperature
- 55 °C
Procedure
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+), 7.83 (2H, m, Hm of pyridinium), 8.44 (1H, m, Hp of pyridinium), 8.89 (1H, m, Ho of pyridinium), uv (H2O) λmax : 266 (ε3550) mμ.
Workup
- temperaturecooled to 23° C.
- washThe aqueous solution was washed with ether (6×4 mL)
- customto remove traces of organic solvents
- additionpoured on top of a column (2.5×10.0 cm) of μ-bondapak C-18
- washThe column was eluted with water and lyophilization of the appropriate fractions
Sources & evidence
- ORD record
- ord-cb9a395027324448b351e0a09fd7b043
- Source dataset
- uspto-grants-1985_11
- Patent number
- US04552696
Linked notes
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