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

HRID 236048Notes

Reaction equation

[CH3:1][S:2]([O:5][CH2:6][CH2:7][S:8][C:9]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:4])=[O:3].[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][S:2]([O-:5])(=[O:4])=[O:3].[C:16]1([C:9]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[S:8][CH2:7][CH2:6][N+:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 90 °C

Procedure

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.

Workup

temperatureAfter cooling to 25° C.
customthe pyridine was evaporated under reduced pressure to a white solid which
customwas triturated in ether
filtrationfiltered 0.66 g, (92%), mp 135°-50° C. dec. ir (KBr) νmax

Sources & evidence

ORD record: ord-80da2b4759f14bc8acb2f7a46378eae1
Source dataset: uspto-grants-1987_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04642341

Reaction notes

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