Sodium Bicarbonate → 2-(4-chlorophenyl)-4-hydroxy-1-[4-(methylsulfonyl)phenyl]-4-((4-chlorophenoxy)methyl]-4,5-dihydro-1H-imidazole

HRID 1166326Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1166326
[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-:22].[Na+].BrCC(=O)[CH2:29][C:30]1C=CC=C[C:31]=1[O:36][C:37]1[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=1>CC(C)=O>[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)[CH2:29][C:30]([OH:22])([CH2:31][O:36][C:37]3[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=3)[N:20]=2)=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 229980221-Bromo-3-[(4-chlorophenoxy)phenyl]-2-propanoneHCID 1785047964-chloro-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide

Produkt 1

HCID 106487922-(4-chlorophenyl)-4-hydroxy-1-[4-(methylsulfonyl)phenyl]-4-((4-chlorophenoxy)methyl]-4,5-dihydro-1H-imidazoleAusbeute 35,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a mixture of 4-chloro-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide (Example 1, Step 1) (1 g, 3.24 mmol) and sodium bicarbonate (550 mg, 6.5 mmol) in acetone (100 mL), 1-bromo-3-[(4-chlorophenoxy)phenyl]-2-propanone from Step 2 (1.5 g, 5.8 mmol) was added. After heating to reflux for 24 hours, the reaction mixture was filtered, washed with acetone and concentrated in vacuo. The crude mixture (2.5 g) was purified by chromatography (silica gel, toluene/ethyl acetate, 1/1) to give 2-(4-chlorophenyl)-4-hydroxy-1-[4-(methylsulfonyl)phenyl]-4-[(4-chlorophenoxy)methyl]-4,5-dihydro-1H-imidazole (565 mg, 35%) as a white solid.

Aufarbeitung

  1. additionwas added
  2. temperatureAfter heating
  3. temperatureto reflux for 24 hours
  4. filtrationthe reaction mixture was filtered
  5. washwashed with acetone
  6. concentrationconcentrated in vacuo
  7. customThe crude mixture (2.5 g) was purified by chromatography (silica gel, toluene/ethyl acetate, 1/1)

Quellen und Nachweise

ORD-Eintrag
ord-1b70502cdbdf443cbf32f5415a5377c6
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06613789B2

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