Water → Ethyl 2-[7-bromo-3-(4-bromo-2-fluorobenzyl)-1,2,3,4-tetrahydro-2,4-dioxoquinazolin-1-yl]acetate

HRID 1639313

Reaktionsgleichung

Reaktionsgleichung von HRID 1639313
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:22])[N:7]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][C:15]=3[F:21])[C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28].O>CN(C)C=O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:22])[N:7]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][C:15]=3[F:21])[C:8](=[O:12])[N:9]2[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 144590037-Bromo-3-(4-bromo-2-fluorobenzyl)-1,2,3,4-tetrahydro-2,4-dioxoquinazoline

Produkt 1

HCID 14458963Ethyl 2-[7-bromo-3-(4-bromo-2-fluorobenzyl)-1,2,3,4-tetrahydro-2,4-dioxoquinazolin-1-yl]acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 7-bromo-3-(4-bromo-2-fluorobenzyl)-1,2,3,4-tetrahydro-2,4-dioxoquinazoline 2.80 g) in N,N-dimethylformamide (56 ml) was added sodium hydride (60% in mineral oil, 334 mg) with stirring at 0° C. under an atmosphere of nitrogen and the mixture was stirred at room temperature for 1 hour. To this mixture was added ethyl bromoacetate (0.85 ml) dropwise and the mixture was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure to give a residue, which was poured into water and extracted with ethyl acetate. The extract was washed with water and dried. Removal of the solvent followed by recrystallization from isopropyl ether gave ethyl 2-[7-bromo-3-(4-bromo-2-fluorobenzyl)-1,2,3,4-tetrahydro-2,4-dioxoquinazolin-1-yl]acetate (3.11 g).

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. stirringthe mixture was stirred at room temperature for 2 hours
  3. customThe solvent was removed under reduced pressure
  4. customto give a residue, which
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. customdried
  8. customRemoval of the solvent
  9. customfollowed by recrystallization from isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-e258b80085a740d9a43f6943e22a17f3
Quelldatensatz
uspto-grants-1989_11
Patentnummer
US04883800

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