Hydrochloric Acid → HCID 66778855, compound

Temperature

80 °C

To a mixture of 3-bromo-2-[chloro(cyclohexyl)methyl]-5-methoxy-1-benzofuran (1.73 g) synthesized above, methyl 4-aminobenzoate (878 mg), sodium iodide (1.45 g) and N,N-dimethylformamide (30 mL) was added sodium carbonate (1.03 g), and the mixture was stirred at 80° C. for 8 hr. 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 (25% ethyl acetate/hexane) to give a yellow oil. To a mixture of the obtained oil, tetrahydrofuran (10 mL) and ethanol (10 mL) was added 1N aqueous sodium hydroxide solution (10.0 mL), and the mixture was stirred with heating under reflux for 5 hr, and concentrated under reduced pressure. The residue was dissolved in water (20 mL), and 1N hydrochloric acid (10.0 mL) was added at 0° C. The resulting precipitate was collected by filtration to give the title object compound (318 mg, 14%) as a pale-brown solid.

1. customto quench
2. customthe reaction
3. extractionthe mixture was extracted with ethyl acetate
4. washThe extract was washed with saturated brine
5. dry with materialdried over magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by silica gel column chromatography (25% ethyl acetate/hexane)
8. customto give a yellow oil
9. stirringthe mixture was stirred
10. temperaturewith heating
11. temperatureunder reflux for 5 hr
12. concentrationconcentrated under reduced pressure
13. dissolutionThe residue was dissolved in water (20 mL)
14. addition1N hydrochloric acid (10.0 mL) was added at 0° C
15. filtrationThe resulting precipitate was collected by filtration

ORD record

ord-ad7853184b7c42e098fa73f8f9a8e459

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08436043B2