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Hydrochloric Acid → 2,3-Difluoro-6-(2,2-diethoxycarbonylethenyl)amino-[(2-p-toluenesulfonyloxypropyl)oxy]benzene

HRID 846330
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 846330
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([NH:9][CH:10]=[C:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:3]=1[O:22][CH2:23][CH:24]([OH:26])[CH3:25].[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1.C(OCC)(=O)C.Cl>N1C=CC=CC=1>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([NH:9][CH:10]=[C:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:3]=1[O:22][CH2:23][CH:24]([O:26][S:33]([C:30]1[CH:31]=[CH:32][C:27]([CH3:37])=[CH:28][CH:29]=1)(=[O:35])=[O:34])[CH3:25]
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Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 146971832,3-Difluoro-6-(2,2-diethoxycarbonylethenyl)amino-[(2-hydroxypropyl)oxy]benzene

Produkt 1

HCID 146971842,3-Difluoro-6-(2,2-diethoxycarbonylethenyl)amino-[(2-p-toluenesulfonyloxypropyl)oxy]benzeneAusbeute 94,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a solution of 747 mg of the compound obtained in Example 3 in 2 ml of pyridine was added 710 mg of p-toluenesulfonyl chloride and the mixture was stirred under cooling with ice for 24 hours, and then at room temperature for 4 hours. To the mixture were added ethyl acetate and 1 N hydrochloric acid. The mixture was shaken, and the organic layer was separated. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified through silica gel column chromatography to yield 1.0 g of the titled compound.

Aufarbeitung

  1. temperatureunder cooling with ice for 24 hours
  2. stirringThe mixture was shaken
  3. customthe organic layer was separated
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customThe residue was purified through silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7f9f974044b74eb39507be53a4072bb3
Quelldatensatz
uspto-grants-1992_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05136059

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