Reaktion #80588

Reaktionsgleichung

4-chloro-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide

sodium bicarbonate

1-bromo-3-[(4-chlorophenoxy)phenyl]-2-propanone

→

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

Ausbeute 35.5%

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   TemperaturAfter heating
3. 3
   Temperaturto reflux for 24 hours
4. 4
   Filtrationthe reaction mixture was filtered
5. 5
   Waschenwashed with acetone
6. 6
   Einengenconcentrated in vacuo
7. 7
   SonstigeThe crude mixture (2.5 g) was chromatographed (silica gel, toluene/ethyl acetate, 1/1)

Vorschrift

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 chromatographed (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.

Quelle