Tin tetrachloride → 2-[2-(2-thienylcarbonyl)-1H-pyrrol-1-yl]-1H-isoindole-1,3(2H)dione

HRID 22396

反応式

HRID 22396 の反応式
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](Cl)=[O:7].[Sn](Cl)(Cl)(Cl)Cl.[N:14]1([N:19]2[C:27](=[O:28])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]2=[O:29])[CH:18]=[CH:17][CH:16]=[CH:15]1>C(Cl)Cl>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([C:15]1[N:14]([N:19]2[C:27](=[O:28])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]2=[O:29])[CH:18]=[CH:17][CH:16]=1)=[O:7]

参加物

5

反応物 3

HCID 24287Tin tetrachlorideHCID 789282-Thiophenecarbonyl chlorideHCID 8537192-(1H-Pyrrol-1-yl)isoindoline-1,3-dione

生成物 1

HCID 199731582-[2-(2-thienylcarbonyl)-1H-pyrrol-1-yl]-1H-isoindole-1,3(2H)dione

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of 2-thiophenecarbonylchloride (10.7 ml) in 500 ml of dry DCM was treated at -10° C. with tin tetrachloride (11.7 ml) and stirred for 30 minutes. 2-(1H-pyrrol-1-yl)-1H-isoindole-1,3(2H)dione (21.2 g) was then added in small portions over a period of 30 minutes at -10° C. After the addition was completed, the reaction mixture was stirred for an additional 30 minutes at -10° C. and subsequently poured into 500 ml of ice water. The precipitate was dissolved by addition of about 1000 ml of DCM and the separated aqueous layer extracted again with DCM. The combined organic layers were washed twice with 2N hydrochloric acid and with water, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by flash column chromatography (silica gel, DCM/ethyl acetate 99:1) and the desired fractions were concentrated. The residue was recrystallized from DCM/ethyl ether affording the product as crystals (17.9 g), m.p. 165°-166° C.

後処理

  1. additionAfter the addition
  2. stirringthe reaction mixture was stirred for an additional 30 minutes at -10° C.
  3. extractionthe separated aqueous layer extracted again with DCM
  4. washThe combined organic layers were washed twice with 2N hydrochloric acid and with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by flash column chromatography (silica gel, DCM/ethyl acetate 99:1)
  8. concentrationthe desired fractions were concentrated
  9. customThe residue was recrystallized from DCM/ethyl ether affording the product as crystals (17.9 g), m.p. 165°-166° C.

出典と根拠

ORDレコード
ord-f39d34e49ba848f1a443ec206f20e892
出典データセット
uspto-grants-1995_06
特許番号
US05428053

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