تفاعل #8253

معادلة التفاعل

sodium bicarbonate

Pyridine

5-Amino-2-(4-methylimidazol-1-yl)fluorobenzene

benzyl chloroformate

→

title product

المردود 92.9%

5-Benzyloxycarbonylamino-2-(4-methylimidazol-1-yl)fluorobenzene

المردود 92.9%

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooled to −5°
2. 2
   أخرىthe organic layer separated
3. 3
   استخلاصthe aqueous layer re-extracted with dichloromethane (2×200 ml)
4. 4
   تجفيفcombined organics dried (magnesium sulfate)
5. 5
   ترشيحAfter filtration and evaporation
6. 6
   أخرىthe residue was recrystallised from toluene (300 ml)

الإجراء التجريبي

5-Amino-2-(4-methylimidazol-1-yl)fluorobenzene (50.6 g, 0.265 M) was dissolved in dry dichloromethane (800 ml) under nitrogen, and cooled to −5°. Pyridine (26.1 g, 0.33 M) was added, followed by benzyl chloroformate (49.9 g, 0.292 M) over 30 minutes. The mixture was stirred and the temperature allowed to rise to ambient over 16 hours. Aqueous sodium bicarbonate (5%, 350 ml) was added, the organic layer separated, and the aqueous layer re-extracted with dichloromethane (2×200 ml), and combined organics dried (magnesium sulfate). After filtration and evaporation, the residue was recrystallised from toluene (300 ml) to give title product (80 g).

المصدر