Tin tetrachloride → 2-[(3-Methyl-2-thienyl)carbonyl-1H-pyrrol-1-yl]-1H-isoindole-1,3(2H)dion

HRID 22399

반응식

HRID 22399 반응식
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([OH:9])=O.C(Cl)(=O)C(Cl)=O.[Sn](Cl)(Cl)(Cl)Cl.[N:21]1([N:26]2[C:34](=[O:35])[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]2=[O:36])[CH:25]=[CH:24][CH:23]=[CH:22]1>C(Cl)Cl.O>[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([C:22]1[N:21]([N:26]2[C:34](=[O:35])[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]2=[O:36])[CH:25]=[CH:24][CH:23]=1)=[O:9]

참가 물질

7

반응물 4

HCID 24287Tin tetrachlorideHCID 65578Oxalyl chlorideHCID 902693-Methyl-2-thenoic acidHCID 8537192-(1H-Pyrrol-1-yl)isoindoline-1,3-dione

생성물 1

HCID 199731602-[(3-Methyl-2-thienyl)carbonyl-1H-pyrrol-1-yl]-1H-isoindole-1,3(2H)dion수율 25.2%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

To a stirred solution consisting of 3-methyl-2-thiophenecarboxylic acid (21.0 g) in dry DCM (1.5 l) was added oxalyl chloride (21.0 ml) at room temperature under nitrogen. After stirring for 1 hour at room temperature, the reaction mixture was cooled to -10° C. and tin (IV) chloride (17.3 ml) was added. The resulting solution was stirred for 10 minutes (-10° C.) at which time 2-(1H-pyrrol-1-yl)-1H-isoindole-1,3(2H)dione (31.3 g) was added in three portions. After stirring for 1 hour in the cooling bath, the reaction mixture was poured into cold water and the layers separated. The organic phase was washed twice with 5% HCl (aq.) and dried (MgSO4). Filtration and concentration gave the crude product. Purification via preparative HPLC (silica gel, DCM) afforded 12.5 g of the product as a solid, m.p. 221°-223° C.

후처리

  1. temperaturethe reaction mixture was cooled to -10° C.
  2. additionwas added in three portions
  3. stirringAfter stirring for 1 hour in the cooling bath
  4. customthe layers separated
  5. washThe organic phase was washed twice with 5% HCl (aq.)
  6. dry with materialdried (MgSO4)
  7. filtrationFiltration and concentration
  8. customgave the crude product
  9. customPurification via preparative HPLC (silica gel, DCM)

출처 및 근거

ORD 기록
ord-2cae46611d054557b1f2884d62f68941
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05428053

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