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

Sodium Carbonate → 2-benzyl-5-(4-chlorophenyl)-4-methoxypyridazin-3(2H)-one

HRID 2224278
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2224278
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]([O:15][CH3:16])=[C:11](Cl)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CCO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([N:8]1[C:13](=[O:14])[C:12]([O:15][CH3:16])=[C:11]([C:22]2[CH:23]=[CH:24][C:19]([Cl:18])=[CH:20][CH:21]=2)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 135262132-Benzyl-5-chloro-4-methoxypyridazin-3(2H)-one2×

Produkt 1

HCID 569275222-benzyl-5-(4-chlorophenyl)-4-methoxypyridazin-3(2H)-oneAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 21863594Toluene ethanolLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 2-benzyl-5-chloro-4-methoxypyridazin-3(2H)-one (20 g, 80 mmol) and 4-chlorophenylboronic acid (15.6 g, 100 mmol) in toluene/EtOH (2:1, 600 mL) at RT under argon was added (Ph3P)4Pd (1.85 g, 1.8 mmol) and 2 M aqueous Na2CO3 solution (160 mL, 320 mmol). The resulting suspension was heated at 90° C. for 16 h with stirring. HPLC/MS indicated about 4% of the 2-benzyl-5-chloro-4-methoxypyridazin-3(2H)-one still remained. After cooling the reaction mixture to RT, the solution was extracted with CH2Cl2 (2×150 mL). The combined organic layers were dried (Na2SO4), filtered and concentrated under vacuum. The crude product was purified by silica gel column chromatography (ISCO) eluting with hexanes/EtOAc to obtain pure title compound, 2-Benzyl-5-(4-chlorophenyl)-4-methoxypyridazin-3(2H)-one, (21.7 g, 83%) as a white solid. MS [M+H]+ 327; HPLC retention time=3.85 min.

Aufarbeitung

  1. temperatureAfter cooling the reaction mixture to RT
  2. extractionthe solution was extracted with CH2Cl2 (2×150 mL)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe crude product was purified by silica gel column chromatography (ISCO)
  7. washeluting with hexanes/EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-4745776979814042a16b71a1b2b7d3f8
Quelldatensatz
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07378418B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion