Sodium Carbonate → 1-(4-Oxo-5-phenyl-3,4-dihydroquinazolin-2-yl)cyclopropanecarbonitrile

HRID 2036832Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2036832
[C:1]([C:3]1([C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:10]=2[C:21]([NH2:23])=[O:22])=O)[CH2:5][CH2:4]1)#[N:2].C([O-])([O-])=O.[Na+].[Na+]>CO>[O:22]=[C:21]1[C:10]2[C:9](=[CH:14][CH:13]=[CH:12][C:11]=2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:8]=[C:6]([C:3]2([C:1]#[N:2])[CH2:5][CH2:4]2)[NH:23]1

Komponenten

4

Edukt 2

HCID 10340Sodium CarbonateHCID 670558893-(1-Cyanocyclopropanecarboxamido)biphenyl-2-carboxamide

Produkt 1

HCID 1363920661-(4-Oxo-5-phenyl-3,4-dihydroquinazolin-2-yl)cyclopropanecarbonitrileAusbeute 113,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution 3-(1-cyanocyclopropanecarboxamido)biphenyl-2-carboxamide (0.7 g, 2 mmol) in methanol was added saturated aqueous Na2CO3 (23 mmol) and the reaction mixture stirred at 80° C. for 30 min. The reaction mixture was concentrated under reduced pressure and the resulting residue was diluted with ethyl acetate then washed with water. The organic extracts were dried, concentrated and purified by silica gel chromatography (4% MeOH in DCM) to yield 1-(4-oxo-5-phenyl-3,4-dihydroquinazolin-2-yl)cyclopropanecarbonitrile (0.65 g, 99% yield) as a white solid. LCMS Method T: retention time 1.810 min; [M+1]=288.2.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe resulting residue was diluted with ethyl acetate
  3. washthen washed with water
  4. customThe organic extracts were dried
  5. concentrationconcentrated
  6. custompurified by silica gel chromatography (4% MeOH in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-3a1ff1fd1c9744deb44f16ab95fb6fc6
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08575184B2

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