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

HRID 745979Notes

Reaction equation

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

Participants

Reactant 3

HCID 702Ethanol

HCID 24386Thionyl Chloride

HCID 56009Rolafagrel

Product 1

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

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-22e6a0ee08d54ba68fb78bd2c8fcf36a
Source dataset: uspto-grants-1986_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04602022

Reaction notes

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