تفاعل #8249

معادلة التفاعل

sodium bicarbonate

Pyridine

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

benzyl chloroformate

→

title product

المردود 93.5%

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

المردود 93.5%

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 (2×300 ml)
4. 4
   تجفيفdried (magnesium sulfate)
5. 5
   ترشيحAfter filtration and evaporation
6. 6
   أخرىthe residue was recrystallised from toluene (400 ml)

الإجراء التجريبي

5-Amino-2-(2-methylimidazol-1-yl)fluorobenzene (34.25 g, 0.179 M) was dissolved in dry dichloromethane (600 ml) under nitrogen, and cooled to −5°. Pyridine (17.7 g, 0.224 M) was added, followed by benzyl chloroformate (33.7 g, 0.197 M) over 20 minutes. The mixture was stirred and the temperature allowed to rise to ambient over 16 hours. Aqueous sodium bicarbonate (5%, 250 ml) was added, the organic layer separated, the aqueous layer re-extracted with dichloromethane (2×300 ml), and combined extracts dried (magnesium sulfate). After filtration and evaporation, the residue was recrystallised from toluene (400 ml) to give title product (54.5 g).

المصدر