Ethyl Acetate → HCID 59331291, compound

Temperature

60 °C

Commercially available ethyl (2-formamido-1,3-thiazol-4-yl)(oxo)acetate (5.09 g, 22.3 mmol) was dissolved in a mixed solvent of ethanol (50 mL) and 1,4-dioxane, and 30% sulfuric acid (12 mL) was added, followed by stirring at 60° C. for 1 hour. The reaction solution was cooled to room temperature, water (20 mL) and ethyl acetate (20 mL) were added, and the solution was separated. The solvent was distilled off under reduced pressure, and 30% sulfuric acid (40 mL) and potassium bromide (9.3 g, 78.2 mmol) were added, followed by cooling to 0° C. Sodium nitrite (20.0 g, 290 mmol) was dissolved in water (40 mL), followed by dropwise addition over 1 hour, and stirring was further carried out at 0° C. for 1 hour. The solution was separated with ethyl acetate (200 mL), the organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=0%-20%) to afford the desired compound (3.07 g, yield 52%) as a yellow oil.

1. additionwas added
2. temperatureThe reaction solution was cooled to room temperature
3. customthe solution was separated
4. additionwere added
5. temperatureby cooling to 0° C
6. additionfollowed by dropwise addition over 1 hour
7. stirringstirring
8. waitwas further carried out at 0° C. for 1 hour
9. customThe solution was separated with ethyl acetate (200 mL)
10. washthe organic layer was washed with saturated brine
11. dry with materialsubsequently dried over anhydrous magnesium sulfate
12. distillationThe solvent was distilled off under reduced pressure
13. customthe resulting residue was purified
14. washsilica gel column chromatography (elution solvent: ethyl acetate/hexane=0%-20%)

ORD record

ord-81ab46a328c54872b0c28674d8e828a0

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08415359B2