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

HRID 1901280

Reaktionsgleichung

Reaktionsgleichung von HRID 1901280
[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]

Komponenten

7

Edukt 4

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

Produkt 1

HCID 199731782-[2-(1H-Pyrrol-2-ylcarbonyl)-1H-pyrrol-1-yl]-1H-isoindole-1,3(2H)dioneAusbeute 69,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-96f92038e9c0438db2f149cbe84b8826
Quelldatensatz
uspto-grants-1996_11
Patentnummer
US05576446

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