反应详情

温度

-24 °C

To 18 g (69.16 mmol) of ethyl 4-(4-nitrophenyl)-1H-pyrrole-3-carboxylate suspended in 300 cm3 of dichloromethane are added, at a temperature in the region of −24° C. under an argon atmosphere, 8.1 cm3 (91.29 mmol) of chlorosulfonyl isocyanate dissolved in 100 cm3 of dichloromethane. After stirring for 30 minutes at a temperature in the region of −24° C., the reaction medium is allowed to warm to a temperature in the region of 20° C. over 2 hours. After initiating the crystallization using a glass rod, the reaction mixture is stirred at a temperature in the region of 20° C. for 30 minutes. The reaction mixture is then cooled to a temperature in the region of 5° C. and then filtered through a No 3 sinter funnel. The solid is washed with three times 40 cm3 of dichloromethane and then dried under reduced pressure (2.7 kPa) at a temperature in the region of 40° C. for 3 hours. The solid is then suspended in 500 cm3 of water; the resulting mixture is then heated at a temperature in the region of 40° C. for 3 hours and then cooled at a temperature in the region of 5° C. for 1 hour before filtering through a No 3 sinter funnel. The solid is successively washed with twice 50 cm3 of water and twice 30 cm3 of petroleum ether and then dried under reduced pressure (2.7 kPa) at a temperature in the region of 40° C. for 16 hours to give 15.4 g of ethyl 5-carbamoyl-4-(4-nitrophenyl)-1H-pyrrole-3-carboxylate in the form of a beige-coloured solid; EI: m/z=303: M+; m/z=274 [M-CH2CH3]+; m/z=258 [M-OCH2CH3]+; m/z=241 [258-OH]+ base peak.

1. additionare added, at a temperature in the region of −24° C. under an argon atmosphere
2. temperatureto warm to a temperature in the region of 20° C. over 2 hours
3. customthe crystallization
4. stirringthe reaction mixture is stirred at a temperature in the region of 20° C. for 30 minutes
5. temperatureThe reaction mixture is then cooled to a temperature in the region of 5° C.
6. filtrationfiltered through a No 3 sinter funnel
7. washThe solid is washed with three times 40 cm3 of dichloromethane
8. customdried under reduced pressure (2.7 kPa) at a temperature in the region of 40° C. for 3 hours
9. temperaturethe resulting mixture is then heated at a temperature in the region of 40° C. for 3 hours
10. temperaturecooled at a temperature in the region of 5° C. for 1 hour
11. filtrationbefore filtering through a No 3 sinter funnel
12. washThe solid is successively washed with twice 50 cm3 of water and twice 30 cm3 of petroleum ether
13. customdried under reduced pressure (2.7 kPa) at a temperature in the region of 40° C. for 16 hours