تفاعل #80580

معادلة التفاعل

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

sodium bicarbonate

2,4'-dibromoacetophenone

→

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

المردود 64.0%

المذيبات

isopropanol

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added
2. 2
   درجة الحرارةAfter heating the reaction mixture at 80°-85° C. for 18 hours
3. 3
   أخرىthe solvent was removed
4. 4
   workup.DISSOLUTIONThe residue was redissolved in methylene chloride
5. 5
   غسيلwashed with aqueous sodium bicarbonate and water
6. 6
   تجفيفdried over sodium sulfate
7. 7
   ترشيحfiltered
8. 8
   تركيزconcentrated in vacuo
9. 9
   أخرىThe crude product (810 mg) was chromatographed (silica gel, hexane/ethyl acetate, 6/4)

الإجراء التجريبي

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 (30 mL), 2,4'-dibromoacetophenone (720 mg, 2.58 mmol) was added. After heating the reaction mixture at 80°-85° C. for 18 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 (810 mg) was chromatographed (silica gel, hexane/ethyl acetate, 6/4) to give 4-(4-bromophenyl)-2-(4-chlorophenyl)-1-[4-(methylsulfonyl)phenyl]-1H-imidazole (400 mg, 64%) as a pale yellow solid: mp 145°-48° C. Anal. Calc'd. for C22H16N2SO2BrCl: C, 54.17, H, 3.31, N, 5.74, S, 6.57. Found: C, 54.41, H, 3.33, N, 5.50, S, 6.52.

المصدر