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

HRID 52299Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 52299
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6571ChloroacetoneLösungsmittel

Versuchsvorschrift

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 chromatographed (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.

Aufarbeitung

  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 chromatographed (silica gel, hexane/ethyl acetate, 25/75)

Quellen und Nachweise

ORD-Eintrag
ord-d9d6189eed734af8b574c54a76545eb9
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616601

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