Sodium Hydroxide → 4-Methoxy-7-(tetrahydro-pyran-4-yl)-benzooxazol-2-ylamine

HRID 1611939Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1611939
COC(=O)[NH:4][C:5]1[O:6][C:7]2[C:13]([CH:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)=[CH:12][CH:11]=[C:10]([O:20][CH3:21])[C:8]=2[N:9]=1.[OH-].[Na+]>O1CCOCC1.C(O)CO>[CH3:21][O:20][C:10]1[C:8]2[N:9]=[C:5]([NH2:4])[O:6][C:7]=2[C:13]([CH:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[CH:12][CH:11]=1

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 23593640[4-Methoxy-7-(tetrahydro-pyran-4-yl)-benzooxazol-2-yl]-carbamic acid methyl ester

Produkt 1

HCID 222522334-Methoxy-7-(tetrahydro-pyran-4-yl)-benzooxazol-2-ylamineAusbeute 74,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 174Ethylene GlycolLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a stirred solution of 130 g (4.24 mmol) [4-methoxy-7-(tetrahydro-pyran-4-yl)-benzooxazol-2-yl]-carbamic acid methyl ester in 90 ml dioxane and 30 ml ethylene glycol was added 90 ml of a 5 N aq. sodium hydroxide solution, and the mixture was heated at 100° C. for 16 h. After cooling to room temperature, the mixture was poured onto water and extracted four times with ethyl acetate. The combined organic phases were dried over sodium sulphate and concentrated in vacuo. Flash chromatography (dichloromethane then 5/95 methanol/dichloromethane) afforded 0.78 g (74%) 4-methoxy-7-(tetrahydro-pyran-4-yl)-benzooxazol-2-ylamine as a brown solid. ES-MS m/e (%): 249 (M+H+, 100).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. additionthe mixture was poured onto water
  3. extractionextracted four times with ethyl acetate
  4. dry with materialThe combined organic phases were dried over sodium sulphate
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f82c0e72b049405cba7fa3830faa2dc1
Quelldatensatz
uspto-grants-2006_01
Patentnummer
US06992083B2

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