Phenacyl bromide → 3,5-Dimethyl-2-[4-(4-phenacyloxybenzoyl)benzylthio]-4-(3H)-quinazolinone

HRID 1291378Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1291378
[OH:1][C:2]1[CH:30]=[CH:29][C:5]([C:6]([C:8]2[CH:28]=[CH:27][C:11]([CH2:12][S:13][C:14]3[N:23]([CH3:24])[C:22](=[O:25])[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][C:20]=4[CH3:26])[N:15]=3)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[CH2:31](Br)[C:32]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:33].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:24][N:23]1[C:22](=[O:25])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][C:20]=2[CH3:26])[N:15]=[C:14]1[S:13][CH2:12][C:11]1[CH:27]=[CH:28][C:8]([C:6](=[O:7])[C:5]2[CH:4]=[CH:3][C:2]([O:1][CH2:31][C:32]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[O:33])=[CH:30][CH:29]=2)=[CH:9][CH:10]=1

Komponenten

5

Edukt 3

HCID 6259Phenacyl bromideHCID 11430Potassium CarbonateHCID 189188882-[4-(4-hydroxybenzoyl)benzylthio]-3,5-dimethyl-4(3H)-quinazolinone

Produkt 1

HCID 189192383,5-Dimethyl-2-[4-(4-phenacyloxybenzoyl)benzylthio]-4-(3H)-quinazolinoneAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 2-[4-(4-hydroxybenzoyl)benzylthio]-3,5-dimethyl-4(3H)-quinazolinone (413 mg), phenacyl bromide (315 mg) and potassium carbonate (436 mg) in DMF (7 ml) was stirred at room temperature for 15 hours. This reaction mixture was concentrated and the residue was dissolved in chloroform, washed with water, dried, and concentrated. The residue was recrystallized from chloroform-ethyl acetate to provide the title compound as colorless solid (313 mg).

Aufarbeitung

  1. concentrationThis reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in chloroform
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was recrystallized from chloroform-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-677699f60dc042a898c85d79f5510111
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05753664

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