Methyl iodide → 1-[8-(tert-Butyl)-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-1-ethanone

HRID 1295999Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1295999
[C:1](=O)([O-])[O-].[K+].[K+].CI.[C:9]([C:13]1[C:22]2[O:21][CH2:20][CH2:19][NH:18][C:17]=2[CH:16]=[C:15]([C:23](=[O:25])[CH3:24])[CH:14]=1)([CH3:12])([CH3:11])[CH3:10]>CN(C)C=O>[C:9]([C:13]1[C:22]2[O:21][CH2:20][CH2:19][N:18]([CH3:1])[C:17]=2[CH:16]=[C:15]([C:23](=[O:25])[CH3:24])[CH:14]=1)([CH3:12])([CH3:10])[CH3:11]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 589099341-[8-(tert-butyl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-1-ethanone

Produkt 1

HCID 589100321-[8-(tert-Butyl)-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-1-ethanoneAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Potassium carbonate (2.43 g, 17.6 mmol) and methyl iodide (1.3 ml, 20.9 mmol) were added to a solution of the 1-[8-(tert-butyl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-1-ethanone (3.73 g, 16.0 mmol) in dimethylformamide (35 ml) under a nitrogen atmosphere, and the mixture was stirred at room temperature for 1 day. The solvent was distilled off under reduced pressure, ethyl acetate was added to the residue and the mixture was washed with water (twice) and brine in that order. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was subjected to silica gel chromatography (Wakogel-C200,60 g) and then fractionated with 2% ethyl acetate-toluene to yield the title compound (2.61 g, 66.0% yield) as bright golden yellow crystals.

Aufarbeitung

  1. distillationThe solvent was distilled off under reduced pressure, ethyl acetate
  2. additionwas added to the residue
  3. washthe mixture was washed with water (twice) and brine in that order
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1baacb61486140bfaeedb3f092bd6fe6
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07244730B2

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