Pyridine → 1-{2-[(Triphenylmethyl)sulfanyl]ethyl}pyridin-1-ium methanesulfonate

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(triphenylmethylthio)ethyl methanesulfonate (0.598 g, 1.50 mmol), tetra-n-butylammonium iodide (0.020 g) and pyridine. (1.2 mL, 15.0 mmol) was heated at 90° C. under a nitrogen atmosphere for 3 h. After cooling to 25° C., the pyridine was evaporated under reduced pressure to a white solid which was triturated in ether and filtered 0.66 g, (92%), mp 135°-50° C. dec. ir (KBr) νmax : 1628 (pyridinium), 1590, 1575 (phenyl), 1190 cm-1 (sulfonate), 1Hmr (DMSO-d6) δ: 2.31 (3H, s, CH3SO3-), 2.82 (2H, m, CH2S), 4.40 (2H, m, CH2N+), 7.28 (15H, m, phenyl), 8.12 (2H, m, Hm of pyridinium), 8.59 (1H, m, Hp of pyridinium), 8.84-8.85 (2H, dd, J=1.3 Hz, J=6.7 Hz, Ho of pyridinium). Anal. calcd. for C27H37NO3S2.H2O: C 65.43, H 5.90, N 2.83, S 12.94; found: C 65.77, H 5.81, N 3.25, S 12.55.

Provenance & Evidence