Triethylamine → 5-Methoxy-2-(methylamino)-4H-3,1-benzoxazin-4-one

HRID 598069

Reaktionsgleichung

Reaktionsgleichung von HRID 598069
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:3]=1[C:4]([OH:6])=[O:5].[CH3:13][N:14]=[C:15]=O.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C>O1CCOCC1.O>[CH3:12][O:11][C:7]1[C:3]2[C:4](=[O:6])[O:5][C:13]([NH:14][CH3:15])=[N:1][C:2]=2[CH:10]=[CH:9][CH:8]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27353572-Amino-6-methoxybenzoic Acid

Produkt 1

HCID 672673385-Methoxy-2-(methylamino)-4H-3,1-benzoxazin-4-oneAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 2-amino-6-methoxybenzoic acid (2.00 g, 12.0 mmol) and methylisocyanate (1.00 g, 17.5 mmol) in dioxane (50 ml) was stirred at 80° C. for 2 h. After cooling to room temperature, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (6.88 g, 36.0 mmol) and triethylamine (5.00 ml, 36.0 mmol) were added. The mixture was stirred at room temperature for 16 h, diluted with water and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and concentrated under vacuum. The residue was purified by column chromatography eluting with 20% ethyl acetate/n-hexane to afford 1.06 g (43%) of the title compound.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. stirringThe mixture was stirred at room temperature for 16 h
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by column chromatography
  8. washeluting with 20% ethyl acetate/n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-0c9d21e66dd648f997dd41525663635f
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897607B2

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