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

HRID 1451969

반응식

HRID 1451969 반응식
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](O)=[O:7].C(Cl)(=O)C(Cl)=O.[Sn](Cl)(Cl)(Cl)Cl.[N:20]1([N:25]2[C:33](=[O:34])[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26]2=[O:35])[CH:24]=[CH:23][CH:22]=[CH:21]1>C(Cl)Cl.O>[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([C:21]1[N:20]([N:25]2[C:33](=[O:34])[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26]2=[O:35])[CH:24]=[CH:23][CH:22]=1)=[O:7]

참가 물질

7

반응물 4

HCID 12473Pyrrole-2-Carboxylic AcidHCID 24287Tin tetrachlorideHCID 65578Oxalyl chlorideHCID 8537192-(1H-Pyrrol-1-yl)isoindoline-1,3-dione

생성물 1

HCID 199731782-[2-(1H-Pyrrol-2-ylcarbonyl)-1H-pyrrol-1-yl]-1H-isoindole-1,3(2H)dione수율 69.2%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

반응 조건

온도
-10 °C

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.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 1 hour
  3. stirringby stirring at -10° C. for additional 30 minutes
  4. extractionextracted with DCM
  5. washThe combined extracts were washed with 1N sodium hydroxide solution, 1N sulfuric acid
  6. dry with materialThe dried (magnesium sulfate) organic phase
  7. filtrationwas filtered
  8. customevaporated in vacuo
  9. customThe residue was triturated with DCM

출처 및 근거

ORD 기록
ord-8174b0ccfb67422bbc6147234b801c69
출처 데이터셋
uspto-grants-1997_02
특허 번호
US05605925

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