Water → HCID 18509225, Verbindung

HRID 1356681Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1356681
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][O:12][CH3:13])(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15].[Cl:17][C:18]1[CH:19]=[C:20]([N+:25]([O-:27])=[O:26])[CH:21]=[CH:22][C:23]=1F.[H-].[Na+].O>CN(C=O)C.C(OCC)C>[Cl:17][C:18]1[CH:19]=[C:20]([N+:25]([O-:27])=[O:26])[CH:21]=[CH:22][C:23]=1[N:11]([O:12][CH3:13])[S:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([N+:14]([O-:16])=[O:15])[CH:4]=1)(=[O:10])=[O:9]

Komponenten

7

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 676882-Chloro-1-fluoro-4-nitrobenzeneHCID 18509259Benzenesulfonamide, 4-chloro-N-methoxy-3-nitro-

Produkt 1

HCID 18509225HCID 18509225, VerbindungAusbeute 12 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 4-chloro-N-methoxy-3-nitrobenzenesulfonamide (0.53 g (1.99 mmol)) and 3-chloro-4-fluoronitrobenzene (1.05 g (5.98 mmol) in 5.0 ml of DMF, sodium hydride (60%, 0.09 g (2.25 mmol)) was added bit by bit with stirring under cooling with ice, and the mixture was stirred under cooling with ice for one hour and at room temperature for 2 hours. Water and diethyl ether were added to the resulting mixture and insolubles were removed by filtration. The filtrate was allowed to stand somewhile and then, the organic layer was separated and washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure The residue was subjected to silica gel column chromatography with ethyl acetate-hexane (1:5) as eluent to give 0.10 g (12%) of the title compound as pale yellow-white crystals.

Aufarbeitung

  1. temperatureunder cooling with ice
  2. stirringthe mixture was stirred
  3. customwere removed by filtration
  4. customthe organic layer was separated
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure The residue

Quellen und Nachweise

ORD-Eintrag
ord-d6a068caa5294193b44a7516d79c16c6
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06586617B1

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