반응 #80579

반응 방정식

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

수율 36.3%

용매

isopropanol

반응 조건

후처리

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

실험 절차

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.

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