Sodium Bicarbonate → 1h-Imidazole,2-(4-chlorophenyl)-4-(3-fluorophenyl)-1-[4-(methylsulfonyl)phenyl]-

HRID 1352934Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1352934
[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+].[F:26][C:27]1[CH:28]=[C:29]([CH:34]=[CH:35][CH:36]=1)[C:30](=O)[CH2:31]Br>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)[CH:31]=[C:30]([C:29]3[CH:34]=[CH:35][CH:36]=[C:27]([F:26])[CH:28]=3)[N:20]=2)=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 27374513-Fluorophenacyl bromideHCID 1785047964-chloro-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide

Produkt 1

HCID 221489891h-Imidazole,2-(4-chlorophenyl)-4-(3-fluorophenyl)-1-[4-(methylsulfonyl)phenyl]-Ausbeute 50,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

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 (30 mL), 3-fluorophenacyl bromide (0.97 g, 4.48 mmol) was added. After heating the reaction mixture at 75–80° 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 was purified by chromatography (silica gel, hexane/ethyl acetate, 6/4) to give 2-(4-chlorophenyl)-4-(3-fluorophenyl)-1-[4-(methylsulfonyl)phenyl)-1H-imidazole (481 mg, 50%) as a white solid: mp 194–196° C. Anal. Calc'd. for C22H16N2SO2FCl: C, 61.90; H, 3.78; N, 6.56; S, 7.51. Found: C, 61.71; H, 3.59; N, 6.42; S, 7.69.

Aufarbeitung

  1. additionwas added
  2. temperatureAfter heating the reaction mixture at 75–80° C. for 18 hours
  3. customthe solvent was removed
  4. dissolutionThe residue was redissolved in methylene chloride
  5. washwashed with aqueous sodium bicarbonate and water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by chromatography (silica gel, hexane/ethyl acetate, 6/4)

Quellen und Nachweise

ORD-Eintrag
ord-7f93841ab7964dc68d5c2fbd2c9ef4dc
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07220770B2

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