StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Dimethylacetamide → methyl 8-(1-(3,5-difluorophenylamino)ethyl)-2-(ethylthio)-4-oxo-4H-chromene-6-carboxylate

HRID 572812
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 572812
Br[C:2]1[CH:3]=[C:4]([C:16]([O:18][CH3:19])=[O:17])[CH:5]=[C:6]2[C:11]=1[O:10][C:9]([S:12][CH2:13][CH3:14])=[CH:8][C:7]2=[O:15].[F:20][C:21]1[CH:22]=[C:23]([CH:25]=[C:26]([F:28])[CH:27]=1)[NH2:24].[CH3:29][C:30](N(C)C)=O>O.C(OCC)(=O)C>[F:20][C:21]1[CH:22]=[C:23]([NH:24][CH:29]([C:2]2[CH:3]=[C:4]([C:16]([O:18][CH3:19])=[O:17])[CH:5]=[C:6]3[C:11]=2[O:10][C:9]([S:12][CH2:13][CH3:14])=[CH:8][C:7]3=[O:15])[CH3:30])[CH:25]=[C:26]([F:28])[CH:27]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 31374DimethylacetamideHCID 965953,5-DifluoroanilineHCID 58235026methyl 8-bromo-2-(ethylthio)-4-oxo-4H-chromene-6-carboxylate

Produkt 1

HCID 58235050methyl 8-(1-(3,5-difluorophenylamino)ethyl)-2-(ethylthio)-4-oxo-4H-chromene-6-carboxylateAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22728543
Water ethylacetate
Lösungsmittel

Versuchsvorschrift

Methyl 8-bromo-2-(ethylthio)-4-oxo-4H-chromene-6-carboxylate (850 mg, 2.29 mmol, prepared as described in Example 9) and 3,5-difluoroaniline (621 mg, 4.81 mmol) in DMA (10 mL) were stirred at 50° C. overnight. The reaction mixture was diluted with water/ethyl acetate. The organic layer was washed with brine, dried over MgSO4 and concentrated. The crude product was purified by flash chromatography on silica gel eluting with 0 to 25% ethyl acetate in dichloromethane. The solvent was evaporated to dryness to afford methyl 8-(1-(3,5-difluorophenylamino)ethyl)-2-(ethylthio)-4-oxo-4H-chromene-6-carboxylate (550 mg, 57%) as a off-white solid. Mass Spectrum: M+H+ 420. SNH

Aufarbeitung

  1. washThe organic layer was washed with brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe crude product was purified by flash chromatography on silica gel eluting with 0 to 25% ethyl acetate in dichloromethane
  5. customThe solvent was evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-3e9e99c499cc4543bdf22e3cfa9334b2
Quelldatensatz
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09029374B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion