Reaktion #80579

Reaktionsgleichung

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

sodium bicarbonate

2-chloro-4'-fluoroacetophenone

→

2-(4-chlorophenyl) -4-(4-fluorophenyl)-1-[4-(methylsulfonyl)phenyl]-1H-imidazole

Ausbeute 36.3%

Lösungsmittel

isopropanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   TemperaturAfter heating the reaction mixture at 80°-85° C. for 48 hours
3. 3
   Sonstigethe solvent was removed
4. 4
   workup.DISSOLUTIONThe residue was redissolved in methylene chloride
5. 5
   Waschenwashed with aqueous sodium bicarbonate and water
6. 6
   Trocknendried over sodium sulfate
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated in vacuo
9. 9
   SonstigeThe crude product (800 mg) was chromatographed (silica gel, hexane/ethyl acetate, 1/1)

Vorschrift

To a mixture of 4-chloro-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide (Example 1, Step 1) (400 mg, 1.29 mmol) and sodium bicarbonate (216 mg, 2.59 mmol) in isopropanol (25 mL), 2-chloro-4'-fluoroacetophenone (670 mg, 3.87 mmol) was added. After heating the reaction mixture at 80°-85° C. for 48 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 (800 mg) was chromatographed (silica gel, hexane/ethyl acetate, 1/1) to give 2-(4-chlorophenyl) -4-(4-fluorophenyl)-1-[4-(methylsulfonyl)phenyl]-1H-imidazole (200 mg, 36%) as a pale yellow solid: mp (DSC) 180° C. Anal. Calc'd. for C22H16N2SO2FCl: C, 61.90, H, 3.78, N, 6.56, S, 7.51. Found: C, 61.92, H, 3.74, N, 6.43, S, 7.62.

Quelle