Hydrochloric Acid → HCID 68511333, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3-[chloro(cyclohexyl)methyl]-2,5-dimethylthiophene (653 mg) synthesized above, methyl 4-aminobenzoate (813 mg), sodium iodide (806 mg) and N,N-dimethylacetamide (15 mL) was added sodium carbonate (570 mg), and the mixture was stirred overnight at 100° C. under an argon atmosphere. 1N Hydrochloric acid was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with 1N hydrochloric acid and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4, volume ratio) to give a white solid. To a mixture of the obtained solid, tetrahydrofuran (10 mL) and ethanol (10 mL) was added 1N aqueous sodium hydroxide solution (10 mL), and the mixture was stirred with heating under reflux overnight, and concentrated under reduced pressure. The residue was dissolved in water (20 mL), 1N hydrochloric acid (10 mL) was added at 0° C. The resulting precipitate was collected by filtration to give the title compound (815 mg, 88%) as a white solid.

Provenance & Evidence