Methanol → HCID 66696224, Verbindung

HRID 1396661Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1396661
[CH3:1][O:2][CH2:3][C:4]1[CH:13]=[C:12]([N:14]2[CH:18]=[CH:17][N:16]=[C:15]2[CH:19]2[CH2:23][CH2:22][O:21][CH2:20]2)[C:11]([N+:24]([O-])=O)=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7].[Cl-].[NH4+].O1CCCC1.CO>O>[NH2:24][C:11]1[C:12]([N:14]2[CH:18]=[CH:17][N:16]=[C:15]2[CH:19]2[CH2:23][CH2:22][O:21][CH2:20]2)=[CH:13][C:4]([CH2:3][O:2][CH3:1])=[C:5]([CH:10]=1)[C:6]([O:8][CH3:9])=[O:7]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 86701153HCID 86701153, Verbindung

Produkt 1

HCID 66696224HCID 66696224, VerbindungAusbeute 86,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a mixture of 6.65 g of methyl 2-(methoxymethyl)-5-nitro-4-[2-(tetrahydrofuran-3-yl)-1H-imidazol-1-yl]benzoate, 980 mg of ammonium chloride, 33.0 mL of tetrahydrofuran, 66.0 mL of methanol, and 33.0 mL of water was added 4.8 g of reduced iron, followed by stirring at 70° C. for 4.5 hours. The insoluble matter was filtered through celite. The filtrate was concentrated, and water and ethyl acetate were added thereto, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform/methanol) to obtain 5.30 g of methyl 5-amino-2-(methoxymethyl)-4-[2-(tetrahydrofuran-3-yl)-1H-imidazol-1-yl]benzoate as a brown solid.

Aufarbeitung

  1. filtrationThe insoluble matter was filtered through celite
  2. concentrationThe filtrate was concentrated
  3. additionwater and ethyl acetate were added
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (chloroform/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-aab383657729478fb4a6a013895fbf10
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901126B2

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