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

HRID 1352927Notes

Reaction equation

HRID 1352927 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-04b0576a51424f07805ef5c2aceb4b7e
Source dataset
uspto-grants-2007_05
Patent number
US07220770B2

Reaction notes

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