Hydrochloric Acid → 1H-Imidazole-2-ethanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1-((4-nitrophenyl)methyl)-

Reaktionsgleichung

Cl.C([O:9][CH2:10][CH2:11][C:12]1[N:13]([CH2:29][C:30]2[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=2)[C:14]([S:20][C:21]2[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=2)=[C:15]([CH:17]([CH3:19])[CH3:18])[N:16]=1)C1C=CC=CC=1.C(=O)([O-])O.[Na+]>>[Cl:27][C:25]1[CH:26]=[C:21]([S:20][C:14]2[N:13]([CH2:29][C:30]3[CH:31]=[CH:32][C:33]([N+:36]([O-:38])=[O:37])=[CH:34][CH:35]=3)[C:12]([CH2:11][CH2:10][OH:9])=[N:16][C:15]=2[CH:17]([CH3:19])[CH3:18])[CH:22]=[C:23]([Cl:28])[CH:24]=1

Komponenten

Edukt 3

HCID 313Hydrochloric Acid

HCID 516892Sodium Bicarbonate

HCID 178907742-(2-benzyloxyethyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1-p-nitrobenzyl-1H-imidazole

Produkt 1

HCID 4740671H-Imidazole-2-ethanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1-((4-nitrophenyl)methyl)-Ausbeute 33 %

Versuchsvorschrift

To 5 ml of concentrated hydrochloric acid was dissolved 1.3 g (2.34 mmol) of the benzyl compound (125a), the mixture was refluxed with heating for 4 hours and worked up. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was washed with water and dried, distilled off, the residual oil was treated with ether, arid crystallized to give 5-(3,5-dichlorophenylthio)-2-(2-hydroxyethyl)-4-isopropyl-1-p-nitrobenzyl-1H-imidazole (126a). m.p. 169-171° C.