Dichloromethane → 2-(1-methyl-1H-indol-3-yl)-3-phenyl-N-methylmaleimide

HRID 1168658

Reaktionsgleichung

Reaktionsgleichung von HRID 1168658
C(Cl)Cl.[CH3:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]2[C:19](=[O:20])[N:18]([CH3:21])[C:16](=[O:17])[C:15]=2Br)=[CH:6]1.ClS(O)(=O)=O.CC(C)C(N)=O.[CH3:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]>C(#N)C>[CH3:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]2[C:19](=[O:20])[N:18]([CH3:21])[C:16](=[O:17])[C:15]=2[C:36]2[CH:35]=[CH:34][CH:39]=[CH:38][CH:37]=2)=[CH:6]1

Komponenten

7

Edukt 5

HCID 6344DichloromethaneHCID 8058HexaneHCID 24638Chlorosulfonic acidHCID 68424IsobutyramideHCID 98184713-Bromo-1-methyl-4-(1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione

Produkt 1

HCID 178436842-(1-methyl-1H-indol-3-yl)-3-phenyl-N-methylmaleimide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Into methylene chloride (83 ml) was dissolved the resultant IM-4 (25 g, 80.5 mmol) obtained as described above, and to this was added dropwise chlorosulfonic acid (8.3 ml) at room temperature. After this mixture was stirred for an hour at room temperature, to the reaction system were added dropwise at a low speed dimethylacetoamide (90 ml)/acetonitrile (45 ml). To this was added dropwise oxy-salt phosphor (15 ml) while being heated and refluxed. After this mixture was heated and refluxed for an hour, hexane (150 ml) was added, then, the mixture was stirred and stood still, and thereafter, the upper layer of hexane was separated and concentrated. The concentrated substances were refined with silica gel column chromatography to obtain 21 g of IM-5.

Aufarbeitung

  1. customobtained
  2. additionTo this was added dropwise oxy-salt phosphor (15 ml)
  3. temperaturewhile being heated
  4. temperaturerefluxed
  5. temperatureAfter this mixture was heated
  6. temperaturerefluxed for an hour
  7. stirringthe mixture was stirred
  8. customthe upper layer of hexane was separated
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-bb987a43e59f48e0a2f68bba9e46ebb8
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06627099B2

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