Dimethylformamide → HCID 22251491, Verbindung

HRID 1180813Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1180813
[C:1]1([CH:7]=[CH:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(S(NN)(=O)=[O:24])C=CC=CC=1.CN([CH:31]=[O:32])C>>[O:10]=[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:8][CH2:7][C:1]1[CH:2]=[CH:3][C:4]([C:31]([OH:32])=[O:24])=[CH:5][CH:6]=1

Komponenten

4

Edukt 3

HCID 6228DimethylformamideHCID 7189CinnamoylbenzeneHCID 65723Benzenesulfonyl hydrazide

Produkt 1

HCID 22251491HCID 22251491, VerbindungAusbeute 31 %

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

To a stirred solution at room temperature of chalcone XXIIIa (1.29 g, 5.13 mmol) in DMF (20 ml) was added phenylsulfonylhydrazine (1.76 g, 10.26 mmol). The reaction mixture was stirred at 10° C. for 15 h, cooled and concentrated. The remained oily residue was partitioned between a saturated aqueous solution of NH4Cl and AcOEt. After separation, the organic layer was dried, partially evaporated and filtered. The filtrate was purified by flash chromatography on silica gel (AcOEt/hexane:50/50□75/25) to form a material which after a second column purification (MeOH/CH2Cl2:5/95) afford the title compound XXVIa (400 mg, 1.59 mmol, 31% yield).

Aufarbeitung

  1. temperaturecooled
  2. concentrationconcentrated
  3. customThe remained oily residue was partitioned between a saturated aqueous solution of NH4Cl and AcOEt
  4. customAfter separation
  5. customthe organic layer was dried
  6. custompartially evaporated
  7. filtrationfiltered
  8. customThe filtrate was purified by flash chromatography on silica gel (AcOEt/hexane:50/50□75/25)
  9. customto form a material which
  10. customafter a second column purification (MeOH/CH2Cl2:5/95)

Quellen und Nachweise

ORD-Eintrag
ord-4e3bb493536b462bbd8696117c8e9a66
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07282608B2

Notizen zur Reaktion

Wird geladen…