반응 #8253

반응 방정식

sodium bicarbonate

Pyridine

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

benzyl chloroformate

→

title product

수율 92.9%

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

수율 92.9%

용매

dichloromethane

반응 조건

후처리

1. 1
   온도cooled to −5°
2. 2
   기타the organic layer separated
3. 3
   추출the aqueous layer re-extracted with dichloromethane (2×200 ml)
4. 4
   건조combined organics dried (magnesium sulfate)
5. 5
   여과After filtration and evaporation
6. 6
   기타the residue was recrystallised from toluene (300 ml)

실험 절차

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).

출처