Ethyl butyrimidate → Ethyl 5-Methyl-2-propyl-3H-imidazole-4-carboxylate

HRID 1492766

Reaktionsgleichung

Reaktionsgleichung von HRID 1492766
Cl.[NH2:2][CH:3]([C:9](=O)[CH3:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:12](=[NH:19])(OCC)[CH2:13][CH2:14][CH3:15]>C(O)C>[CH3:10][C:9]1[N:19]=[C:12]([CH2:13][CH2:14][CH3:15])[NH:2][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Komponenten

4

Edukt 2

HCID 16634Ethyl butyrimidateHCID 13282897Ethyl 2-amino-3-oxobutanoate hydrochloride

Produkt 1

HCID 178440086Ethyl 5-Methyl-2-propyl-3H-imidazole-4-carboxylateAusbeute 37,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Ethyl 2-amino-3-oxobutanoate hydrochloride (10 g) was added to a stirring solution of ethyl butaneimidate (83.5 g) in ethanol (800 ml, freshly distilled from magnesium ethoxide) and triethylamine (85 ml) and the resultant yellow mixture stirred at room temperature for 48 h. The solvent was removed in vacuo and the residue diluted with water (500 ml) and extracted into ethyl acetate (3×200 ml). The combined organic extracts were washed with water (2×100 ml), dried and concentrated in vacuo. The resultant residue was purified by trituration with ether (5×50 ml) and the residual buff solid dried to afford the title compound (4.05 g)

Aufarbeitung

  1. distillationfreshly distilled from magnesium ethoxide) and triethylamine (85 ml)
  2. customThe solvent was removed in vacuo
  3. additionthe residue diluted with water (500 ml)
  4. extractionextracted into ethyl acetate (3×200 ml)
  5. washThe combined organic extracts were washed with water (2×100 ml)
  6. customdried
  7. concentrationconcentrated in vacuo
  8. customThe resultant residue was purified by trituration with ether (5×50 ml)
  9. customthe residual buff solid dried

Quellen und Nachweise

ORD-Eintrag
ord-fee9b42a3a0c46d187b3885dbee8c367
Quelldatensatz
uspto-grants-1994_12
Patentnummer
US05374646

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