Sodium Carbonate → HCID 68516755, compound

Temperature

80 °C

4-Azido-N-ethylbenzamide (0.571 g, 3.00 mmol) and ethyl 4-phenyl-3-oxobutyrate (0.692 g, 3.60 mmol, 1.25 eq.) were dissolved in ethanol (15 ml), sodium ethoxide (284 mg, 3.60 mmol, 1.25 eq.) was added, and the mixture was stirred at room temperature for 30 min and at 80° C. for 2 hr. 2% aqueous sodium carbonate solution (20 ml) was added to the reaction mixture, and the mixture was further stirred for 30 min. Ethanol was evaporated, and the residue was diluted with 2% aqueous sodium carbonate solution (20 ml) and washed with ethyl acetate (40 ml). The organic layer was extracted with 2% aqueous sodium carbonate solution (20 ml). The aqueous layers were combined, concentrated to about 30 ml, acidified (pH<3) with 6N hydrochloric acid and extracted with ethyl acetate (35 ml×2). The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate and concentrated, and diethyl ether and ethyl acetate were added. The precipitate was collected by filtration, washed with diethyl ether and dried to give the title compound as a pale-brown powder (796 mg, 2.27 mmol, 75.7%).

1. stirringthe mixture was further stirred for 30 min
2. customEthanol was evaporated
3. additionthe residue was diluted with 2% aqueous sodium carbonate solution (20 ml)
4. washwashed with ethyl acetate (40 ml)
5. extractionThe organic layer was extracted with 2% aqueous sodium carbonate solution (20 ml)
6. concentrationconcentrated to about 30 ml
7. extractionextracted with ethyl acetate (35 ml×2)
8. washwashed with saturated brine
9. dry with materialdried over anhydrous sodium sulfate
10. concentrationconcentrated
11. additiondiethyl ether and ethyl acetate were added
12. filtrationThe precipitate was collected by filtration
13. washwashed with diethyl ether
14. customdried

ORD record

ord-93525a90738647528caabc80b0159048

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07803822B2