Ammonium Hydroxide → 6-bromo-8-methoxy-4,4-dimethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one

HRID 1278687

Reaktionsgleichung

Reaktionsgleichung von HRID 1278687
[CH3:1][O:2][C:3]1[C:12]2[NH:11][C:10](=[O:13])[O:9][C:8]([CH3:15])([CH3:14])[C:7]=2[CH:6]=[CH:5][CH:4]=1.C([O-])(=O)C.[Na+].[Br:21]Br.[OH-].[NH4+]>C(O)(=O)C>[Br:21][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:12]2[NH:11][C:10](=[O:13])[O:9][C:8]([CH3:15])([CH3:14])[C:7]=2[CH:6]=1

Komponenten

6

Edukt 4

HCID 14923Ammonium HydroxideHCID 24408BromineHCID 2106172H-3,1-Benzoxazin-2-one, 1,4-dihydro-4,4-dimethyl-8-methoxy-HCID 517045Sodium Acetate

Produkt 1

HCID 235096426-bromo-8-methoxy-4,4-dimethyl-1,4-dihydro-2H-3,1-benzoxazin-2-oneAusbeute 93,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a mixture of 8-methoxy-4,4-dimethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one (2.1 g, 10.1 mmol), sodium acetate (1.5 g, 18 mmol) in acetic acid (30 mL) was added bromine (0.62 mL, 12 mmol) at ambient temperature. After 30 minutes, the solution was treated with a concentrated ammonium hydroxide solution (50 mL). The precipitate was collected on a filter and washed with water (3×20 mL) to yield 6-bromo-8-methoxy-4,4-dimethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one (2.7 g, 93%) as off-white solid: MS (ESI) m/z 286, 288 [M +H]+.

Aufarbeitung

  1. customThe precipitate was collected on
  2. filtrationa filter
  3. washwashed with water (3×20 mL)

Quellen und Nachweise

ORD-Eintrag
ord-4778dc075ee64ab093fa833b1594dd50
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06444668B1

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