Hydrochloric Acid → HCID 178489039, compound

Participants

Reaction Steps

5-(4-Methoxyphenyl)-2-(3-methyl-4-nitrophenyl)-N-(2-thiazolyl)imidazole-4-carboxamide (1.5 g) obtained in Example 84 was dissolved in 50% aqueous ethanol solution (60 ml) and dioxane (50 ml), and iron powder (0.6 g) was added. Conc. hydrochloric acid (0.06 ml) was added under refluxing and the mixture was refluxed for 1 hr. A saturated aqueous hydrogencarbonate solution was added and the mixture was neutralized. An insoluble matter was filtered off and the filtrate was concentrated under reduced pressure. Water was added to the residue and the mixture was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. After drying, the solvent was evaporated under reduced pressure. The obtained crystals (0.79 g) were dissolved in methanol (24 ml) and dioxane (35 ml) and 1 M hydrochloric acid—ether solution (5.85 ml) was added. The mixture was stirred at room temperature for 1 hr. The solvent was evaporated under reduced pressure and the obtained crystals were recrystallized from ethanol to give the objective 2-(4-amino-3-methylphenyl)-5-(4-methoxyphenyl)-N-(2-thiazolyl)imidazole-4-carboxamide. Hydrochloride (0.43 g): melting point 250° C. or above

Provenance & Evidence