반응 #160846

반응 방정식

NaOH

Chlorosulfonyl isocyanate

pyrrole

DMF

→

above compound

수율 73.2%

1H-pyrrole-2,4-dicarbonitrile

수율 73.2%

용매

EtOAc

ACN

ACN

반응 조건

후처리

1. 1
   온도was cooled in an ice/salt bath
2. 2
   workup.ADDITIONadded to the reaction dropwise over the following 30 min
3. 3
   기타The ice/salt bath was removed
4. 4
   온도The solution was then cooled in an ice/salt bath
5. 5
   온도to slowly warm to rt over 17 h
6. 6
   온도The solution was cooled in an ice/salt bath
7. 7
   기타The solution was transferred to a separatory funnel
8. 8
   기타the organic layer was isolated
9. 9
   추출the aqueous layer was back extracted with EtOAc (2×)
10. 10
    세척The collected organic was washed with aq saturated NaHCO3
11. 11
    추출The aqueous layers were back extracted with EtOAc (2×50 mL)
12. 12
    기타The combined organic layers were collected
13. 13
    건조dried (MgSO4)
14. 14
    농축concentrated onto silica gel
15. 15
    기타purified by column chromatography (9:1 v/v CH2Cl2-EtOAc)

실험 절차

To a solution of ACN (15 mL) was added pyrrole (1.03 mL, 14.9 mmol) which was cooled in an ice/salt bath. Chlorosulfonyl isocyanate (2.73 mL, 31.3 mmol) was diluted in ACN (5 mL) and then added to the reaction dropwise over the following 30 min. The ice/salt bath was removed and the solution was allowed to warm to rt over the next 1.5 h. The solution was then cooled in an ice/salt bath and DMF (5.00 mL, 65.0 mmol) was slowly added via an addition funnel. The solution was allowed to slowly warm to rt over 17 h. The solution was cooled in an ice/salt bath and aq 1 N NaOH (50 mL) was added followed by EtOAc (50 mL). The solution was transferred to a separatory funnel, and the organic layer was isolated and the aqueous layer was back extracted with EtOAc (2×). The collected organic was washed with aq saturated NaHCO3 followed by H2O (100 mL). The aqueous layers were back extracted with EtOAc (2×50 mL). The combined organic layers were collected, dried (MgSO4), concentrated onto silica gel, and purified by column chromatography (9:1 v/v CH2Cl2-EtOAc) to afford 1.28 g of the above compound as a white solid (10.9 mmol, yield 73%). 1H-NMR (DMSO-d6) δ 13.29 (br s, 1H), 8.00 (s, 1H), 7.49 (s, 1H); LCMS RT=1.65 min.

출처