반응 #8249

반응 방정식

sodium bicarbonate

Pyridine

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

benzyl chloroformate

→

title product

수율 93.5%

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

수율 93.5%

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 (2×300 ml)
4. 4
   건조dried (magnesium sulfate)
5. 5
   여과After filtration and evaporation
6. 6
   기타the residue was recrystallised from toluene (400 ml)

실험 절차

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).

출처