تفاعل #80588

معادلة التفاعل

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

المردود 35.5%

المذيبات

acetone

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added
2. 2
   درجة الحرارةAfter heating
3. 3
   درجة الحرارةto reflux for 24 hours
4. 4
   ترشيحthe reaction mixture was filtered
5. 5
   غسيلwashed with acetone
6. 6
   تركيزconcentrated in vacuo
7. 7
   أخرىThe crude mixture (2.5 g) was chromatographed (silica gel, toluene/ethyl acetate, 1/1)

الإجراء التجريبي

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.

المصدر