反应详情

To a mixture of 4-chloro-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide (Example 1, Step 1) (700 mg, 2.24 mmol) and sodium bicarbonate (376 mg, 4.48 mmol) in isopropanol (30 mL), 3-fluorophenacyl bromide (0.97 g, 4.48 mmol) was added. After heating the reaction mixture at 75–80° C. for 18 hours, the solvent was removed. The residue was redissolved in methylene chloride and washed with aqueous sodium bicarbonate and water. The organic fractions were combined, dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by chromatography (silica gel, hexane/ethyl acetate, 6/4) to give 2-(4-chlorophenyl)-4-(3-fluorophenyl)-1-[4-(methylsulfonyl)phenyl)-1H-imidazole (481 mg, 50%) as a white solid: mp 194–196° C. Anal. Calc'd. for C22H16N2SO2FCl: C, 61.90; H, 3.78; N, 6.56; S, 7.51. Found: C, 61.71; H, 3.59; N, 6.42; S, 7.69.

1. additionwas added
2. temperatureAfter heating the reaction mixture at 75–80° C. for 18 hours
3. customthe solvent was removed
4. dissolutionThe residue was redissolved in methylene chloride
5. washwashed with aqueous sodium bicarbonate and water
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe crude product was purified by chromatography (silica gel, hexane/ethyl acetate, 6/4)