Hydrochloric Acid → 1H-Imidazole-2-methanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1-(2-(2-pyridinyl)ethyl)-

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Reaction Conditions

Reaction Steps

To 1.43 g of 5-(3,5-dichlorophenylthio)-4-isopropyl-2-(p-methoxybenzyloxymethyl)-1-(2-(2-pyridyl)ethyl)-1H-imidazole was added 20 ml of ethanol and 40 ml of 36% hydrochloric acid, and the mixture was stirred at 90° C. for 2 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, an aqueous sodium hydrogen carbonate solution was added, and extracted with ethyl acetate. The extract was dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate:methanol=10:1) to give 571 mg of 5-(3,5-dichlorophenylthio)-4-isopropyl-2-hydroxymethyl-1-(2-(2-pyridyl)ethyl)-1H-imidazole (112a) (yield 51%). 1H-NMR (CDCl3 -TMS) δ ppm: 1.29(d,J=6.8 Hz,6H), 3.15(m,3H), 4.52 (m,2H), 4.76(s,2H), 6.87(d,2H), 6.80-7.40(m,3H), 7.60(m,1H),8.50(m,1H); Elementary analysis (C20H21Cl2N3OS); Calc. (%): C,56.87;H,5.01;N,9.95;Cl,16.79;S,7.59; Found (%): C,56.58;H,5.13;N,9.90;Cl,16.65;S,7.53.

Provenance & Evidence