Bromomethyl 4-methoxyphenyl ketone → 2-(4-chlorophenyl)-4-(4-methoxyphenyl)-1-(4-(methylsulfonyl)phenyl]-4-(4-methoxyphenyl)-1H-imidazole

HRID 1166322Notes

Reaction equation

HRID 1166322 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[NH:20])[NH:9][C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[C:21](=[O:24])(O)[O-].[Na+].[CH3:26][O:27][C:28]1[CH:37]=[CH:36][C:31]([C:32](=O)[CH2:33]Br)=[CH:30][CH:29]=1>C(O)(C)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]([C:10]3[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:17])=[O:18])=[CH:12][CH:11]=3)[CH2:33][C:32]([C:2]3[CH:7]=[CH:6][C:5]([O:24][CH3:21])=[CH:4][CH:3]=3)([C:31]3[CH:36]=[CH:37][C:28]([O:27][CH3:26])=[CH:29][CH:30]=3)[N:20]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 516892Sodium BicarbonateHCID 1785047964-chloro-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide

Product 1

HCID 229980782-(4-chlorophenyl)-4-(4-methoxyphenyl)-1-(4-(methylsulfonyl)phenyl]-4-(4-methoxyphenyl)-1H-imidazoleYield 113.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
77.5 °C

Procedure

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 (50 mL), 4-methoxyphenacyl bromide (1.03 g, 4.48 mmol) was added. After heating the reaction mixture at 75-80° C. for 20 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-(4-methoxyphenyl)-1-[4-(methylsulfonyl)phenyl]-4-(4-methoxyphenyl)-1H-imidazole (695 mg, 71%) as a white solid: mp 110-113° C. Anal Calc'd. for C23H19N2SO3Cl: C, 62.94, H, 4.36, N, 6.38, S, 7.30. Found: C, 62.54, H, 4.43, N, 6.17, S, 7.15.

Workup

  1. additionwas added
  2. customthe solvent was removed
  3. dissolutionThe residue was redissolved in methylene chloride
  4. washwashed with aqueous sodium bicarbonate and water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by chromatography (silica gel, hexane/ethyl acetate, 6/4)

Sources & evidence

ORD record
ord-52fc46b3550448c8afac94ea5b37271a
Source dataset
uspto-grants-2003_09
Patent number
US06613789B2

Reaction notes

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