تفاعل #80578

معادلة التفاعل

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

sodium bicarbonate

2-bromoacetophenone

→

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

المردود 57.0%

المذيبات

isopropanol

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added
2. 2
   أخرىthe solvent was removed
3. 3
   workup.DISSOLUTIONThe residue was redissolved in methylene chloride
4. 4
   غسيلwashed with aqueous sodium bicarbonate and water
5. 5
   تجفيفdried over sodium sulfate
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated in vacuo
8. 8
   أخرىThe crude product (1.2 g) was chromatographed on silica gel with toluene/ethyl acetate (75/25)

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 (25 mL), 2-bromoacetophenone (780 mg, 3.87 mmol) was added. After heating the reaction mixture at 55° C. for 20 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 (1.2 g) was chromatographed on silica gel with toluene/ethyl acetate (75/25) to give pure 2-(4-chlorophenyl)-1-[4-(methylsulfonyl)phenyl]-4-phenyl-1H-imidazole (300 mg, 57%) as a white solid: mp (DSC) 202° C. Anal. Calc'd. for C22H17N2SO2Cl: C, 63.78, H, 4.28, N, 6.76, S, 7.74. Found: C, 63.69, H, 4.11, N, 6.68, S, 7.65. ##STR28##

المصدر