Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 70143653, compound

Participants

Reaction Steps

Pyridinium para-toluenesulfonate (33.6 mg, 134.7 mmol) was added to (±)-5,6-dichloro-1-(2,2dimethyl-hexahydro-benzo[1,3]dioxol-5-yl)-1H-benzimidazole (part d of this experiment, 459.6 mg, 1.35 mmol) in methanol (7 ml) and the reaction was heated at reflux for 19 hr and concentrated. The residue was purified by column chromatography eluting with methanol:ethyl acetate (1:9) to give the title compound (184.4 mg, 45%). Rf=0.19 (1:9 methanol:ethyl acetate); 1H-NMR (CD3OD, 300 MHz) δ8.36 (s, 1H), 7.91 (s, 1H), 7.80 (s, 1H), 4.70 (tt, 1H, J=12, 4), 4.11 (d, 1H, J=3), 3.79-3.73 (m, 1H), 2.26 (dq, 1H, J=13, 3), 2.15-2.10 (m, 2H), 2.06-1.99 (m, 2H), 1.88-1.85 (m, 1H); MS (ES) M+H=301.

Provenance & Evidence