Isopropanol → 2-(4-Chlorophenyl)-4-methyl-1-(4-(methylsulfonyl)phenyl)-1H-imidazole

HRID 1166314Notes

Reaction equation

HRID 1166314 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(=O)(O)[O-].[Na+].[CH:26](O)([CH3:28])[CH3:27]>ClCC(=O)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)[CH:27]=[C:26]([CH3:28])[N:20]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 516892Sodium BicarbonateHCID 1785047964-chloro-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide

Product 1

HCID 99462002-(4-Chlorophenyl)-4-methyl-1-(4-(methylsulfonyl)phenyl)-1H-imidazoleYield 67%

Reagents, catalysts & solvents 1

HCID 6571ChloroacetoneSolvent

Procedure

To a mixture of 4-chloro-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide (Example 1, Step 1) (240 mg, 0.78 mmol) and sodium bicarbonate (131 mg, 1.56 mmol) in isopropanol (20 mL), excess chloroacetone (1.5 mL) was added. After heating to reflux, the reaction mixture for 72 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 (370 mg) was purified by chromatography (silica gel, hexane/ethyl acetate, 25/75) to give pure 2-(4-chlorophenyl)-1-[4-(methylsulfonyl)phenyl]-4-methyl-1H-imidazole (160 mg, 67%): mp (DSC) 166° C. Anal Calc'd. for C17H15N2SO2Cl C, 58.87, H, 4.36, N, 8.08 Found: C, 58.78, H, 4.62, N, 7.99.

Workup

  1. additionwas added
  2. temperatureAfter heating
  3. temperatureto reflux
  4. customthe solvent was removed
  5. dissolutionThe residue was redissolved in methylene chloride
  6. washwashed with aqueous sodium bicarbonate and water
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude product (370 mg) was purified by chromatography (silica gel, hexane/ethyl acetate, 25/75)

Sources & evidence

ORD record
ord-85e331f8fc4a4310b3af728d97d95451
Source dataset
uspto-grants-2003_09
Patent number
US06613789B2

Reaction notes

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