Toluene → 2-[2-(Cycloocten-1-yloxy)ethyl]-5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazole

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A solution of the compound 22 (690 mg, 2 mmol) and p-toluenesulfonic acid hydrate (400 mg, 2.1 mmol) in a mixture of tetrahydrofuran (10 mL) - toluene (100 ML) was concentrated under reduced pressure. The residue was dried on an oil bath at 55° C. for 40 minutes. The residue was dissolved in toluene (100 mL), and 1-methoxycyclooctene (1.84 g, 10 mmol) was added thereto. The reaction mixture was heated with reflux over 1 hours and concentrated to a small quantity. After cooling down at room temperature, triethylamine (0.4 mL) was added thereto. The reaction mixture was purified by chromatography on an alumina column (eluate: hexane - ethyl acetate (15:1)) to give the compound 47 (790 mg, 87%). Mp 73-74° C. PMR (CDCl3 -0.1% d5 -Py): δH1.24 (6 H, d, J 4.6 Hz, (CH3)2C), 3.13 (2 H, t, J 4.2 Hz, CH2 -Im), 3.08 (1 H, m, (CH3)2CH), 3.51 (3 H, 8, NCH3), 3.96 (2 H, t, J 4.2 Hz, OCH2), 4.51(1 H, t, J 5.6 Hz, =CH), 6.77 (2 H, d, J 2 Hz, arom-H), 7.09 (1 H, t-like, arom-H). IR(KBr)cm-1 : 3436, 3056, 1659, 1568, 1533, 1500, 1160, 1094. Elementary analysis (for C23H30N2Ocl2S) Calcd. : C, 60.91% H, 6.67% N, 6.18% S, 7.07% Cl, 15.63% Found: C, 60.74% H, 6.69% N, 5.94% S, 6.83% Cl, 15.43%

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