Potassium Carbonate → 3-[2-(5-Methoxy-2-methyl-phenylamino)-ethyl]-oxazolidin-2-one

HRID 270767Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 270767
C1(C)C=CC(S(O[CH2:11][CH2:12][N:13]2[CH2:17][CH2:16][O:15][C:14]2=[O:18])(=O)=O)=CC=1.[CH3:20][C:21]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:22]=1[NH2:23].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:29][O:28][C:25]1[CH:26]=[CH:27][C:21]([CH3:20])=[C:22]([NH:23][CH2:11][CH2:12][N:13]2[CH2:17][CH2:16][O:15][C:14]2=[O:18])[CH:24]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 995005-Methoxy-o-toluidineHCID 157609472-(2-Oxooxazolidin-3-yl)ethyl 4-methylbenzenesulfonate

Produkt 1

HCID 210711283-[2-(5-Methoxy-2-methyl-phenylamino)-ethyl]-oxazolidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a flask was added 2.95 g (10.3 mmol) of Toluene-4-sulfonic acid, 2-(2-oxo-oxazolidin-3-yl)-ethyl ester, 1.56 g (11.4 mmol) of 2-methyl-5-methoxyaniline, 2.58 g (18.7 mmol) of potassium carbonate, and 22 mL of anhydrous dimethylformamide, and the mixture was heated at 100° C. for seven hours. The reaction was allowed to cool to room temperature, and was partitioned between ethyl acetate and water. The phases were separated, and the ethyl acetate phase was washed with brine, dried over Na2SO4, filtered, and concentrated to an oil. The oil was purified by chromatography (120 mL silica, 60 ethyl acetate/40 hexanes) to give the corresponding product as a clear oil that solidified upon drying: 1H NMR (DMSO-d6, 400 MHz) 6.81 (d, 1H), 6.11 (s, 1H), 6.04 (d, 1H), 4.92 (t, 1H), 4.21 (t, 2H), 3.65 (s, 3H), 3.59 (m, 2H), 3.31 (m, 2H), 3.23 (m, 2H), 1.95 (s, 3H) ppm.

Aufarbeitung

  1. temperatureto cool to room temperature
  2. customwas partitioned between ethyl acetate and water
  3. customThe phases were separated
  4. washthe ethyl acetate phase was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to an oil
  8. customThe oil was purified by chromatography (120 mL silica, 60 ethyl acetate/40 hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-14833e54d0ac45178dcb387a4d6a3809
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449576B1

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