Ethanol → 2-Naphthalenecarboxylic acid, 5,6-dihydro-7-(1H-imidazol-1-yl)-, ethyl ester

HRID 745979Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 745979
O=S(Cl)Cl.[N:5]1([C:10]2[CH2:11][CH2:12][C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([C:20]([OH:22])=[O:21])=[CH:15][CH:14]=3)[CH:9]=[CH:8][N:7]=[CH:6]1.[CH3:23][CH2:24]O>>[N:5]1([C:10]2[CH2:11][CH2:12][C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:15][CH:14]=3)[CH:9]=[CH:8][N:7]=[CH:6]1

Komponenten

4

Edukt 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 56009Rolafagrel

Produkt 1

HCID 30215662-Naphthalenecarboxylic acid, 5,6-dihydro-7-(1H-imidazol-1-yl)-, ethyl ester

Versuchsvorschrift

EtOH absolute (14.4 ml) was added slowly to SOCl2 (2.2 ml) at 0° C. and the mixture was heated at room temperature and 1,2-dihydro-3-(1-imidazolyl)-6-carboxy-naphthalene (7 g) was added. The reaction mixture was refluxed for one day, then was stirred overnight at room temperature. The solvent and the excess of SOCl2 were evaporated under reduced pressure and the residue was chromatographed on silica gel using CHCl3 :CH3OH (50:5) as eluant to give 1,2-dihydro-3-(1-imidazolyl)-6-ethoxycarbonyl-naphthalene(6.8 g), m.p. 113°-116° C.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for one day
  2. customThe solvent and the excess of SOCl2 were evaporated under reduced pressure
  3. customthe residue was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-22e6a0ee08d54ba68fb78bd2c8fcf36a
Quelldatensatz
uspto-grants-1986_07
Patentnummer
US04602022

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