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

HRID 1080467

반응식

HRID 1080467 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-92720452a44b4c81bedb4ad9948cd888
출처 데이터셋
uspto-grants-1996_12
특허 번호
US05580987

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