1H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)- → HCID 53817008, Verbindung

HRID 1458587Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1458587
Br[CH2:2][CH2:3][N:4]1[C:8](=[O:9])[C:7]2=[CH:10][CH:11]=[CH:12][CH:13]=[C:6]2[C:5]1=[O:14].[Cl:15][C:16]1[C:17]([NH:31][S:32]([CH3:35])(=[O:34])=[O:33])=[C:18]2[C:23](=[CH:24][C:25]=1[Cl:26])[N:22]=[C:21]([O:27][CH3:28])[C:20]([O:29][CH3:30])=[N:19]2.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:15][C:16]1[C:17]([N:31]([CH2:2][CH2:3][N:4]2[C:8](=[O:9])[C:7]3=[CH:10][CH:11]=[CH:12][CH:13]=[C:6]3[C:5]2=[O:14])[S:32]([CH3:35])(=[O:34])=[O:33])=[C:18]2[C:23](=[CH:24][C:25]=1[Cl:26])[N:22]=[C:21]([O:27][CH3:28])[C:20]([O:29][CH3:30])=[N:19]2

Komponenten

5

Edukt 3

HCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-2×HCID 11430Potassium CarbonateHCID 54321377HCID 54321377, Verbindung

Produkt 1

HCID 53817008HCID 53817008, VerbindungAusbeute 85,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

N-(2-bromoethyl)phthalimide (1.73 g, 6.81 mmol) was added to a refluxing mixture of N-(6,7-dichloro-2,3-dimethoxy-quinoxalin-5-yI)-methanesulphonamide (Preparation 3, 2.00 g, 5.68 mmol) and potassium carbonate (1.88 g, 13.63 mmol) in acetone (100 ml) under nitrogen. After 48 hours, further N-(2-bromoethyl)phthalimide (1.73 g, 6.81 mmol) was added and refluxing continued for 18 hours. After cooling the mixture was concentrated under reduced pressure and the residue dissolved in dichloromethane. The resulting solution was washed twice with 1N sodium hydroxide solution, water and brine and then dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography (eluting with hexane:ethyl acetate) to afford N-(6,7-dichloro-2,3-dimethoxyquinoxalin-5-yl)-N-(2-phthalimidoethyl) methanesulphonamide as a pale yellow solid (2.55g, 85%).

Aufarbeitung

  1. temperaturerefluxing
  2. waitcontinued for 18 hours
  3. temperatureAfter cooling the mixture
  4. concentrationwas concentrated under reduced pressure
  5. dissolutionthe residue dissolved in dichloromethane
  6. washThe resulting solution was washed twice with 1N sodium hydroxide solution, water and brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash chromatography (eluting with hexane:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-e19f6f5dda3c4bf8a574be4ac1a2b0ab
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05852016

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