Thioanisole → HCID 178424021, compound

Participants

Reaction Steps

2-(4-Benzyloxyphenyl)-5-(4-methylphenyl)-N-(2-thiazolyl)-imidazole-4-carboxamide (5.10 g) obtained in Example 22(3) and thioanisole (6.4 ml) were dissolved in trifluoroacetic acid (100 ml) and the mixture was stirred for 6 hr. The reaction mixture was made alkaline with 2 M aqueous sodium hydroxide solution and then acidified withaqueouscitricacid. Themixturewasextractedwithethylacetate. The ethyl acetate layer was washed with saturated brine and, after drying, the solvent was evaporated. The obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=6:4) and recrystallized from ethyl acetate and hexane to give 2-(4-hydroxyphenyl)-5-(4-methylphenyl)-N-(2-thiazolyl)imidazole-4-carboxamide (2.33 g), melting point 286-289° C. (decomposition).

Provenance & Evidence