Chloroacetonitrile → HCID 22097030, Verbindung

HRID 1458561Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1458561
Cl[CH2:2][C:3]#[N:4].[Cl:5][C:6]1[C:7]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])=[C:8]2[C:13](=[CH:14][C:15]=1[Cl:16])[N:12]=[C:11]([O:17][CH3:18])[C:10]([O:19][CH3:20])=[N:9]2.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:5][C:6]1[C:7]([N:21]([CH2:2][C:3]#[N:4])[S:22]([CH3:25])(=[O:24])=[O:23])=[C:8]2[C:13](=[CH:14][C:15]=1[Cl:16])[N:12]=[C:11]([O:17][CH3:18])[C:10]([O:19][CH3:20])=[N:9]2

Komponenten

5

Edukt 3

HCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 54321377HCID 54321377, Verbindung

Produkt 1

HCID 22097030HCID 22097030, VerbindungAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

Chloroacetonitrile (233 μl, 279 mg, 3,69 mmol) was added to a refluxing mixture of N-(6,7-dichloro-2,3-dimethoxyquinoxalin-5-yl)methane-sulphonamide (from Preparation 3, 1.00 g, 2.84 mmol) and potassium carbonate (0.47 g, 3.41 mmol) in acetone (50 ml) under nitrogen. The mixture was refluxed for 18 h and was then allowed to cool, and was partitioned between ethyl acetate (500 ml) and water (500 ml). The organic phase was dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography (eluting with 0-100% ethyl acetate in hexane and then 5% methanol in dichloromethane) to give N-(6,7-dichloro-2,3-dimethoxyquinoxalin-5-yl)-N-(cyanomethyl) methanesulphonamide as an off-white solid (600 mg, 54%).

Aufarbeitung

  1. temperatureThe mixture was refluxed for 18 h
  2. temperatureto cool
  3. customwas partitioned between ethyl acetate (500 ml) and water (500 ml)
  4. dry with materialThe organic phase was dried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography (
  7. washeluting with 0-100% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-14f6b7edb2cc4a298d26aa83bd8b6c29
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05852016

Notizen zur Reaktion

Wird geladen…