Sodium hydride → HCID 178486824, Verbindung

HRID 23347

Reaktionsgleichung

Reaktionsgleichung von HRID 23347
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([OH:10])=[O:9])[CH2:4][CH2:3]1.[H-].[Na+].Cl[C:14]1[CH:23]=[N:22][C:21]2[C:16](=[CH:17][C:18]([O:26][CH3:27])=[C:19]([O:24][CH3:25])[CH:20]=2)[N:15]=1>C1COCC1.CN(C=O)C>[CH3:25][O:24][C:19]1[CH:20]=[C:21]2[C:16](=[CH:17][C:18]=1[O:26][CH3:27])[N:15]=[C:14]([O:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([OH:10])=[O:9])[CH2:4][CH2:3]1)[CH:23]=[N:22]2

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 225731372-Chloro-6,7-dimethoxyquinoxalineHCID 178525780HCID 178525780, Verbindung

Produkt 1

HCID 178486824HCID 178486824, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of cis/trans-4-hydroxy-cyclohexanecarboxylic acid (144 mg, 1 mmol) and NaH (60%, 160 mg, 4 mmol) in anhydrous THF/DMF (10 mL/2 mL) is refluxed for one hour before addition of 2-chloro-6,7-dimethoxyquinoxaline (225 mg, 1 mmol). The resulting mixture is continued to refluxed for four hours. The reaction mixture is neutralized to pH 5 and extracted with ethyl acetate (2×50 mL). The combined organic solutions are dried over magnesium sulfate and filtered. The residue after concentration is chromatographed on silica gel (ethyl acetate, followed by methanol) to provide the desired product as a white solid (m.p. 90-93° C.). Anal. Calcd. for C17H20N2O5.0.5 H2O: C, 59.89; H, 6.19; N, 8.22; Found: C, 59.91; H, 6.62; N, 7.90.

Aufarbeitung

  1. temperatureto refluxed for four hours
  2. extractionextracted with ethyl acetate (2×50 mL)
  3. dry with materialThe combined organic solutions are dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe residue after concentration
  6. customis chromatographed on silica gel (ethyl acetate, followed by methanol)

Quellen und Nachweise

ORD-Eintrag
ord-5f89f2b6a2b94f7fb98289f8b318ad40
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06852712B2

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