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

Potassium Carbonate → HCID 178432322, Verbindung

HRID 220781
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 220781
[C:1]([N:9]1[CH2:15][CH2:14][CH:13](Br)[C:12](=[O:17])[C:11]2[CH:18]=[CH:19][CH:20]=[CH:21][C:10]1=2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[C:23]([NH2:26])(=[NH:25])[CH3:24].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]([N:9]1[CH2:15][CH2:14][C:13]2[N:26]=[C:23]([CH3:24])[NH:25][C:12]=2[C:11]2[CH:18]=[CH:19][CH:20]=[CH:21][C:10]1=2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:1]([N:9]1[CH2:15][CH2:14][C:13]2[N:25]=[C:23]([CH3:24])[O:17][C:12]=2[C:11]2[CH:18]=[CH:19][CH:20]=[CH:21][C:10]1=2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 11430Potassium Carbonate3×HCID 67170Acetamidine monohydrochloride3×HCID 231123501-Benzoyl-4-bromo-1,2,3,4-tetrahydro-benzo[b]azepin-5-one

Produkt 2

HCID 231123696-benzoyl-2-methyl-5,6-dihydro-4H-1-oxa-3,6-diaza-benzo[e]azuleneAusbeute 4 %HCID 178432322HCID 178432322, Verbindung
Ausbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

1-Benzoyl-4-bromo-1,2,3,4-tetrahydro-benzo[b]azepin-5-one (67.5 g, 200 mmol) from Example E5.7, acetamidine hydrochloride (92.7 g, 980 mmol) and potassium carbonate (136.0 g, 980 mmol) were suspended in acetonitrile (2.0 liters) and heated at reflux for 17 h under nitrogen. Additional acetamidine hydrochloride (18.5 g, 200 mmol) and potassium carbonate (27.7 g, 200 mmol) were added and the reaction mixture was heated at reflux for a further 6 h. Additional acetamidine hydrochloride (18.5 g, 200 mmol) and potassium carbonate (27.7 g, 200 mmol) were added again and the reaction mixture was heated at reflux for a further 6 h. On cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated in vacuo. The residue was taken up in dichloromethane (1.4 liters), washed with water (500 ml), dried over sodium sulfate, filtered and reduced in vacuo. The crude products were purified by flash chromatography on silica gel (eluant; 45% EtOAc:45% acetonitrile: 10% methanol) to yield the title compound (26.7 g, 34%) and 6-benzoyl-2-methyl-5,6-dihydro-4H-1-oxa-3,6-diaza-benzo[e]azulene (3.3 g, 4%).

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 17 h under nitrogen
  3. temperaturethe reaction mixture was heated
  4. temperatureat reflux for a further 6 h
  5. temperaturethe reaction mixture was heated
  6. temperatureat reflux for a further 6 h
  7. filtrationthe reaction mixture was filtered
  8. concentrationthe filtrate was concentrated in vacuo
  9. washwashed with water (500 ml)
  10. dry with materialdried over sodium sulfate
  11. filtrationfiltered
  12. customThe crude products were purified by flash chromatography on silica gel (eluant; 45% EtOAc:45% acetonitrile: 10% methanol)

Quellen und Nachweise

ORD-Eintrag
ord-40ee044daf72473a993137e1df243929
Quelldatensatz
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08202858B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion