Reaction #80588

Reaction equation

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

Yield 35.5%

Solvents

acetone

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   TemperatureAfter heating
3. 3
   Temperatureto reflux for 24 hours
4. 4
   Filtrationthe reaction mixture was filtered
5. 5
   Washwashed with acetone
6. 6
   Concentrationconcentrated in vacuo
7. 7
   OtherThe crude mixture (2.5 g) was chromatographed (silica gel, toluene/ethyl acetate, 1/1)

Procedure

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.

Source