Ammonia → HCID 19020738, compound

To a solution of 1.00 g of 5-chloro-2-(2,3-dihydroxypropyl)-1,2-benzoisoxazolin-3-one in tetrahydrofuran (20 ml) was added 0.40 g of trichloromethyl chloroformate and the mixture was stirred at room temperature. After 30 minutes, the reaction mixture was cooled to 5° C. followed by adding dropwise 0.42 g of triethylamine. After stirring at the same temperature for 30 minutes, 5.0 ml of a 28% ammonia solution was added. Furthermore, after stirring at room temperature for 2 hours, the reaction mixture was refluxed by heating for 3 hours followed by concentration under reduced pressure. The residue was dissolved in ethyl acetate (100 ml) and the solution was washed with a 10% NaCl solution. The organic layer was dried over anhydrous magnesium sulfate and the drying agent was removed by filtration. The solvent was distilled off under reduced pressure and the residue was purified by column chromatography (developing solvent: ethyl acetate) through silica gel to afford 0.75 g (64.1%) of the title compound having melting point 161°-162° C. as a colorless powder.

1. temperaturethe reaction mixture was cooled to 5° C.
2. stirringAfter stirring at the same temperature for 30 minutes
3. stirringFurthermore, after stirring at room temperature for 2 hours
4. temperaturethe reaction mixture was refluxed
5. temperatureby heating for 3 hours
6. concentrationfollowed by concentration under reduced pressure
7. dissolutionThe residue was dissolved in ethyl acetate (100 ml)
8. washthe solution was washed with a 10% NaCl solution
9. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
10. customthe drying agent was removed by filtration
11. distillationThe solvent was distilled off under reduced pressure
12. customthe residue was purified by column chromatography (developing solvent: ethyl acetate) through silica gel

ORD record

ord-3b9a1dd2619a451588aae47913480f95

Source dataset

uspto-grants-1992_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05116839