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

HRID 50701Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 50701
[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-d23a2f6976df402baeefab153d55e184
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713478B2

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