4-Bromophenacyl bromide → 4-(4-bromophenyl)-2-(4-chlorophenyl)-1-[4-(methylsulfonyl)phenyl]-1H-imidazole

Participants

Reaction Steps

To a mixture of 4-chloro-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide (Example 1, Step 1) (400 mg, 1.29 mmol) and sodium bicarbonate (216 mg, 2.59 mmol) in isopropanol (30 mL), 2,4′-dibromoacetophenone (720 mg, 2.58 mmol) was added. After heating the reaction mixture at 80–85° 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 (810 mg) was purified by chromatography (silica gel, hexane/ethyl acetate, 6/4) to give 4-(4-bromophenyl)-2-(4-chlorophenyl)-1-[4-(methylsulfonyl)phenyl]-1H-imidazole (400 mg, 64%) as a pale yellow solid: mp 145–48° C. Anal. Calc'd. for C22H16N2SO2BrCl: C, 54.17; H, 3.31; N, 5.74; S, 6.57. Found: C, 54.41; H, 3.33; N, 5.50; S, 6.52.

Provenance & Evidence