Hydrochloric Acid → HCID 66777972, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3-[chloro(cyclohexyl)methyl]-1-benzothiophene (2.42 g) synthesized above, methyl 4-aminobenzoate (2.77 g), sodium iodide (2.74 g) and N,N-dimethylacetamide (50 mL) was added sodium carbonate (1.94 g), and the mixture was stirred under argon atmosphere at 100° C. overnight. 1N Hydrochloric acid was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:3, volume ratio) to give a pale-yellow oil. To a mixture of the obtained oil, tetrahydrofuran (20 mL) and ethanol (20 mL) was added 1N aqueous sodium hydroxide solution (20 mL), and the mixture was stirred overnight with heating under reflux. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in water (40 mL), and 1N hydrochloric acid (20 mL) was added at 0° C. The resulting precipitate was collected by filtration to give the title object compound (1.80 g, 54%) as a white solid.

Provenance & Evidence