Water → 2-[2-(2-Methyl-1-oxopropyl)-1H-pyrrol-1-yl]-1H-isoindole-1,3(2H)dione

HRID 327842

반응식

HRID 327842 반응식
[C:1](Cl)(=[O:5])[CH:2]([CH3:4])[CH3:3].[Sn](Cl)(Cl)(Cl)Cl.[N:12]1([N:17]2[C:25](=[O:26])[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]2=[O:27])[CH:16]=[CH:15][CH:14]=[CH:13]1.O>C(Cl)Cl>[CH3:3][CH:2]([CH3:4])[C:1]([C:13]1[N:12]([N:17]2[C:25](=[O:26])[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]2=[O:27])[CH:16]=[CH:15][CH:14]=1)=[O:5]

참가 물질

6

반응물 4

HCID 962WaterHCID 24287Tin tetrachlorideHCID 62325Isobutyryl chlorideHCID 8537192-(1H-Pyrrol-1-yl)isoindoline-1,3-dione

생성물 1

HCID 199732002-[2-(2-Methyl-1-oxopropyl)-1H-pyrrol-1-yl]-1H-isoindole-1,3(2H)dione

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of isobutyryl chloride (5.4 ml) in DCM (250 ml) was added tin (IV) chloride (5.8 ml) at -10° C. under nitrogen. After stirring for 15 minutes in the cooling bath, 2-(1H-pyrrol-1-yl)-1H-isoindole-1,3(2H)dione (10.0 g) was added portion-wise. The reaction mixture was allowed to warm to room temperature, and stir for three days, at which time it was poured into cold water. The layers were separated and the organic phase was washed twice with water, once with 5% HCl (aq.), and subsequently dried (MgSO4). Filtration and concentration gave the crude product. Purification via preparative HPLC (silica gel, DCM) afforded 2.5 g of the product as a solid, m.p. 147°-149° C.

후처리

  1. additionwas added portion-wise
  2. customThe layers were separated
  3. washthe organic phase was washed twice with water, once with 5% HCl (aq.)
  4. dry with materialsubsequently dried (MgSO4)
  5. filtrationFiltration and concentration
  6. customgave the crude product
  7. customPurification via preparative HPLC (silica gel, DCM)

출처 및 근거

ORD 기록
ord-4596beb64d1d4249969e62ff0627142b
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05274116

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