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Iodoethane → HCID 22097014, Verbindung

HRID 1458557
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1458557
[NH2:1][C:2]1[C:3]([O:22][CH3:23])=[N:4][C:5]2[C:10]([N:11]=1)=[C:9]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])[C:8]([Cl:17])=[C:7]([C:18]([F:21])([F:20])[F:19])[CH:6]=2.C(=O)([O-])[O-].[K+].[K+].I[CH2:31][CH3:32]>CC(C)=O>[NH2:1][C:2]1[C:3]([O:22][CH3:23])=[N:4][C:5]2[C:10]([N:11]=1)=[C:9]([N:12]([CH2:31][CH3:32])[S:13]([CH3:16])(=[O:15])=[O:14])[C:8]([Cl:17])=[C:7]([C:18]([F:21])([F:20])[F:19])[CH:6]=2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6340Iodoethane2×HCID 11430Potassium CarbonateHCID 22097003HCID 22097003, Verbindung

Produkt 1

HCID 22097014HCID 22097014, VerbindungAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of N-(3-amino-6-chloro-7-trifluoromethyl-2-methoxyquinoxalin-5-yl)methanesulphonamide (Preparation 20, 73 mg, 0.2 mmol) and anhydrous potassium carbonate (33 mg, 0.24 mmol) in acetone was stirred under reflux for 20 mins. Iodoethane (32 μl, 0.4 mmol) was added, and the mixture was heated for a further 2 h. Additional iodoethane (32 μl, 0.4 mmol) was added, and heating was continued for a further 4 h. The mixture was concentrated under reduced pressure and the residue was partitioned between water and ethyl acetate. The organic solution was dried (MgSO4), concentrated under reduced pressure, and the residue was purified by flash chromatography (gradient elution with dichloromethane/methanol) to give N-(3-amino-6-chloro-7-trifluoromethyl-2-methoxyquinoxalin-5-yl)-N-ethyl-methanesulphonamide (75 mg, 96%), as a white solid.

Aufarbeitung

  1. temperatureunder reflux for 20 mins
  2. temperaturethe mixture was heated for a further 2 h
  3. temperatureheating
  4. concentrationThe mixture was concentrated under reduced pressure
  5. customthe residue was partitioned between water and ethyl acetate
  6. dry with materialThe organic solution was dried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. customthe residue was purified by flash chromatography (gradient elution with dichloromethane/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-2c9cd9cd962443f99d0ef8bfb5f389e4
Quelldatensatz
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05852016

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