Ammonium Chloride → 4,6-Diphenyl-4,5-dihydropyridazin-3(2h)-one

HRID 1692703Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1692703
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:9]1([C:15]2[CH:16]=[CH:17][C:18](=[O:21])[NH:19][N:20]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Cl-].[NH4+]>C1COCC1.C1(C)C=CC=CC=1>[C:9]1([C:15]2[CH2:16][CH:17]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:18](=[O:21])[NH:19][N:20]=2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Komponenten

6

Edukt 3

HCID 25517Ammonium ChlorideHCID 751063-Phenyl-6-pyridazoneHCID 178418255HCID 178418255, Verbindung

Produkt 1

HCID 2839154,6-Diphenyl-4,5-dihydropyridazin-3(2h)-oneAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

135 ml (135 mmole) of a solution of phenylmagnesium bromide (1M) in THF was added to a hot suspension of 6-phenylpyridazinone compound 7.8 g (45 mmole) in dry toluene (50 ml). The mixture was refluxed for 8 h, left overnight at ambient temperature, then decomposed with a saturated solution of ammonium chloride. The organic layer was separated, and the aqueous layer was extracted with 100 ml of ethyl acetate. The solvent was removed and the residue was crystallized from ethanol. The crystals were collected by filtering and dried over a medium frit sintered glass funnel in vacuo to give 5.6 g of white crystals. Yield was 50%, confirmed by ESI-MS. ESI-MS: m/z 250.1 (M+H+).

Aufarbeitung

  1. temperatureThe mixture was refluxed for 8 h
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with 100 ml of ethyl acetate
  4. customThe solvent was removed
  5. customthe residue was crystallized from ethanol
  6. customThe crystals were collected
  7. filtrationby filtering
  8. customdried over a medium frit sintered glass funnel in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9f70c175c7c747ef88a26a3795e8f525
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08158627B2

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