반응 #50672

반응 방정식

2-(1H-pyrrol-1-yl)-1H-isoindole-1,3(2H)dione

oxalyl chloride

pyrrole-2-carboxylic acid

tin (IV) chloride

→

product

수율 69.2%

2-[2-(1H-Pyrrol-2-ylcarbonyl)-1H-pyrrol-1-yl]-1H-isoindole-1,3(2H)dione

수율 69.2%

용매

water

DCM

반응 조건

후처리

1. 1
   온도The reaction mixture was heated
2. 2
   온도under reflux for 1 hour
3. 3
   workup.STIRRINGby stirring at -10° C. for additional 30 minutes
4. 4
   추출extracted with DCM
5. 5
   세척The combined extracts were washed with 1N sodium hydroxide solution, 1N sulfuric acid
6. 6
   건조The dried (magnesium sulfate) organic phase
7. 7
   여과was filtered
8. 8
   기타evaporated in vacuo
9. 9
   기타The residue was triturated with DCM

실험 절차

To a suspension of pyrrole-2-carboxylic acid (5.55 g) in 500 ml of DCM was added oxalyl chloride (8.7). The reaction mixture was heated under reflux for 1 hour, cooled to -10° C., and tin (IV) chloride (5.85 ml) was added. After stirring the mixture at -10° C. for 30 minutes, 2-(1H-pyrrol-1-yl)-1H-isoindole-1,3(2H)dione (10.6 g) was added in four portions over a period of 30 minutes, followed by stirring at -10° C. for additional 30 minutes. The reaction mixture was then poured into 500 ml of water and extracted with DCM. The combined extracts were washed with 1N sodium hydroxide solution, 1N sulfuric acid, and finally with water. The dried (magnesium sulfate) organic phase was filtered and evaporated in vacuo. The residue was triturated with DCM, affording the product as a powder (10.55 g), mp 204°-206° C.

출처