Acetone → HCID 15451892, compound

A mixture of (E)-2-(2-acetoxymethylphenyl)-2-hydroxyiminoacetamide (428 mg), potassium carbonate (301 mg) and acetone (3.6 ml) was stirred at room temperature. To the mixture was added dropwise 95% dimethyl sulfate (0.20 ml). The mixture was stirred at room temperature for 4.5 hours. Water (10 ml) was added to the reaction mixture, and the mixture was stirred at room temperature for 30 minutes. Water (30 ml) was added, and the mixture was extracted with ethyl acetate three times. The combined ethyl acetate layer was washed with saturated brine and dried over anhydrous sodium sulfate. Evaporation of the solvent under reduced pressure gave the crude product (440 mg). The crude product was crystallized from ethyl acetate-hexane, the crystallization mother liquor was concentrated and purified by silica gel thin layer chromatography (ethyl acetate:hexane=4:1) to obtain the title compound (432 mg in total, yield 95.6%, colorless crystals).

1. stirringThe mixture was stirred at room temperature for 4.5 hours
2. stirringthe mixture was stirred at room temperature for 30 minutes
3. extractionthe mixture was extracted with ethyl acetate three times
4. washThe combined ethyl acetate layer was washed with saturated brine
5. dry with materialdried over anhydrous sodium sulfate
6. customEvaporation of the solvent under reduced pressure
7. customgave the crude product (440 mg)
8. customThe crude product was crystallized from ethyl acetate-hexane
9. concentrationthe crystallization mother liquor was concentrated
10. custompurified by silica gel thin layer chromatography (ethyl acetate:hexane=4:1)

ORD record

ord-0f6dbc559b3e47daa0375545f233082c

Source dataset

uspto-grants-2000_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06037495