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

HRID 22401

反応式

HRID 22401 の反応式
[C:1](Cl)(=[O:3])[CH3:2].[Sn](Cl)(Cl)(Cl)Cl.[N:10]1([N:15]2[C:23](=[O:24])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]2=[O:25])[CH:14]=[CH:13][CH:12]=[CH:11]1>C(Cl)Cl>[C:1]([C:11]1[N:10]([N:15]2[C:23](=[O:24])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]2=[O:25])[CH:14]=[CH:13][CH:12]=1)(=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 6367Acetyl chlorideHCID 24287Tin tetrachlorideHCID 8537192-(1H-Pyrrol-1-yl)isoindoline-1,3-dione

生成物 1

HCID 199667522-(2-Acetyl-1H-pyrrol-1-yl)-1H-isoindole-1,3(2H)dione

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of acetyl chloride (6.77 ml) in DCM (400 ml) was added tin (IV) chloride (11.14 ml) at -5° C., under nitrogen. 2-(1H-pyrrol-1-yl)-1H-isoindole-1,3(2H)dione (20.0 g) was then added portion-wise, keeping the temperature below 0° C. The reaction mixture was then stirred at 0° C. for 0.5 hour, at which time it was poured into ice water. The layers were separated and the aqueous phase was extracted with DCM. The combined organics were washed twice with 5% HCl (aq.) and dried (MgSO4). Filtration and concentration gave the crude product. Purification via flash column chromatography (silica gel, DCM) afforded 9.62 g of the product as a solid, m.p. 204°-205° C.

後処理

  1. customthe temperature below 0° C
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted with DCM
  4. washThe combined organics were washed twice with 5% HCl (aq.)
  5. dry with materialdried (MgSO4)
  6. filtrationFiltration and concentration
  7. customgave the crude product
  8. customPurification via flash column chromatography (silica gel, DCM)

出典と根拠

ORDレコード
ord-cab4923a9dcb4b90a0b864c5b1457ce1
出典データセット
uspto-grants-1995_06
特許番号
US05428053

関連ノート

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