Sodium Iodide → N-methoxy-N,3,5-trimethyl-1-benzofuran-2-carboxamide

Temperature

50 °C

To a solution (50 mL) of 1-(2-hydroxy-5-methylphenyl)ethanone (5.00 g) in N,N-dimethylformamide were added potassium carbonate (9.20 g), sodium iodide (9.98 g) and 2-chloro-N-methoxy-N-methylacetamide (5.04 g), and the mixture was stirred at 50° C. for 5 hr then at 80° C. overnight. The insoluble material was filtered off, 1,8-diazabicyclo[5.4.0]undec-7-ene (5.00 mL) was added to the filtrate and the mixture was stirred at 120° C. for 2 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 (20% ethyl acetate/hexane) to give the title object compound (3.78 g, 49%) as a brown oil.

1. customat 80° C.
2. customovernight
3. filtrationThe insoluble material was filtered off
4. addition1,8-diazabicyclo[5.4.0]undec-7-ene (5.00 mL) was added to the filtrate
5. stirringthe mixture was stirred at 120° C. for 2 hr
6. addition1N Hydrochloric acid was added
7. customto quench
8. customthe reaction
9. extractionthe mixture was extracted with ethyl acetate
10. washThe extract was washed with saturated brine
11. dry with materialdried over magnesium sulfate
12. concentrationconcentrated under reduced pressure
13. customThe residue was purified by silica gel column chromatography (20% ethyl acetate/hexane)

ORD record

ord-fbc11865480c4359bcf71b757b77eb85

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08436043B2