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

HRID 1080463

反応式

HRID 1080463 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
-10 °C

実験手順

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 tritated with DCM, affording the product as a powder (10.55 g), mp 204°-206° C.

後処理

  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

出典と根拠

ORDレコード
ord-47a0140afefa4bf49208407627bdf272
出典データセット
uspto-grants-1996_12
特許番号
US05580987

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