Methyl iodide → 6-(3-Bromo-5-fluorophenyl)-1,4,4-trimethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one

HRID 1634955Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1634955
[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:21]=[CH:20][C:12]3[NH:13][C:14](=[O:19])[O:15][C:16]([CH3:18])([CH3:17])[C:11]=3[CH:10]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.[H-].[Na+].I[CH3:25].[Cl-].[NH4+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:21]=[CH:20][C:12]3[N:13]([CH3:25])[C:14](=[O:19])[O:15][C:16]([CH3:17])([CH3:18])[C:11]=3[CH:10]=2)[CH:5]=[C:6]([F:8])[CH:7]=1

Komponenten

6

Edukt 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 98098756-(3-Bromo-5-fluorophenyl)-4,4-dimethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one

Produkt 1

HCID 102701136-(3-Bromo-5-fluorophenyl)-1,4,4-trimethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-oneAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 6-(3-bromo-5-fluorophenyl)-4,4-dimethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one (0.34 g, 0.99 mmol) in dry DMF (10 mL) was added under nitrogen at room temperature sodium hydride (80 mg, 2.0 mmol) in one portion. The mixture was stirred at ambient temperature for 30 minutes, treated with iodomethane (1 mL, excess), and stirred for 2 hours. To the reaction mixture was added a cold saturated ammonium chloride solution (30 mL) and the white precipitate obtained was collected on a filter, washed with the distilled water to afford the title compound as a white solid (0.31 g, 87%): mp 157-158° C.; 1H-NMR (DMSO-d6) δ 7.83 (s, 1H), 7.76 (dd, 1H, J=8.5, 2.0 Hz), 7.67 (m, 2H), 7.53 (dt, 1H, J=8.3, 1.9 Hz), 7.18 (d, 1H, J=8.5 Hz), 3.33 (s, 3H), 1.67 (s, 6H); 19F-NMR (DMSO-d6) −111.01 (m, 1F); MS (APCI) m/z 364 ([M+H]+, 96%), 366 ([M+H]+, 100%).

Aufarbeitung

  1. stirringstirred for 2 hours
  2. customthe white precipitate obtained
  3. customwas collected on a filter
  4. washwashed with the distilled water

Quellen und Nachweise

ORD-Eintrag
ord-b75e7c1b5fcb4a7dbad618e4d20a815d
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06509334B1

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