Sodium Hydroxide → HCID 22252238, Verbindung

HRID 1611962Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1611962
COC(=O)[NH:4][C:5]1[O:6][C:7]2[C:13]([NH2:14])=[CH:12][CH:11]=[C:10]([O:15][CH3:16])[C:8]=2[N:9]=1.[OH-].[Na+]>O1CCOCC1.C(O)CO>[CH3:16][O:15][C:10]1[C:8]2[N:9]=[C:5]([NH2:4])[O:6][C:7]=2[C:13]([NH2:14])=[CH:12][CH:11]=1

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 23593643HCID 23593643, Verbindung

Produkt 1

HCID 22252238HCID 22252238, VerbindungAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 174Ethylene GlycolLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a stirred solution of 100 mg (0.42 mmol) (7-amino-4-methoxy-benzooxazol-2-yl)-carbamic acid methyl ester in 15 ml dioxane and 5 ml ethylene glycol was added 15 ml of a 5 N aq. sodium hydroxide solution and the mixture was heated at 100° C. for 4 h. After cooling to room temperature the mixture was poured onto water and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulphate and concentrated in vacuo. Flash chromatography (5/95 methanol/dichloromethane, then 10/89/1 methanol/dichloromethane/triethylamine) followed by trituration in ether afforded 15 mg (20%) 4-methoxy-benzooxazole-2,7-diamine as a brown solid. ES-MS m/e (%): 180 (M+H+, 100).

Aufarbeitung

  1. temperatureAfter cooling to room temperature the mixture
  2. additionwas poured onto water
  3. extractionextracted three 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-8727766e06d747d6b578d8ed5c841459
Quelldatensatz
uspto-grants-2006_01
Patentnummer
US06992083B2

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