Hydrochloric Acid → HCID 22329311, Verbindung

HRID 587054Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 587054
[Br:1][C:2]1[CH:17]=[CH:16][C:5]([N:6]([CH:13]([CH3:15])[CH3:14])[CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[C:4]([CH:18]=O)[CH:3]=1.[C:20](=O)([O-])[O-].[K+].[K+].CI.C(=O)(OC)OC.C[O-].[Na+].CO.Cl>CN(C=O)C>[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]([CH:13]([CH3:15])[CH3:14])[CH2:7][CH2:8][C:9]([C:10]([O:12][CH3:20])=[O:11])=[CH:18][C:4]=2[CH:3]=1

Komponenten

8

Edukt 6

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 12021Dimethyl CarbonateHCID 15552091HCID 15552091, VerbindungHCID 23694274Sodium methanolate methanol

Produkt 1

HCID 22329311HCID 22329311, VerbindungAusbeute 56,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In DMF (4.5 ml) was dissolved 4-(4-bromo-2-formylisopropylanilino)butyric acid (0.9 g). To the solution was added potassium carbonate (0.49 g), followed by addition of methyl iodide (0.2 ml) and stirring at room temperature 1 hour. To the mixture was added dimethyl carbonate (9 ml), followed by addition of a 28% sodium methoxide/methanol solution (1.27 g) and stirring at 50° C. for 1 hour. After cooled to room temperature, the mixture was neutralized with 2N hydrochloric acid, and extracted with ethyl acetate. The extract was washed with saturated brine and dried with magnesium sulfate. The solvent was removed under reduced pressure, and the resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate=20/1→6/1) to give methyl 7-bromo-1-isopropyl-2,3-dihydro-1-benzazepine-4-carboxylate (0.50 g).

Aufarbeitung

  1. stirringstirring at 50° C. for 1 hour
  2. temperatureAfter cooled to room temperature
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried with magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate=20/1→6/1)

Quellen und Nachweise

ORD-Eintrag
ord-194fd2e65e694fb1890cdcc08b8562fd
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06936602B1

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