Water → HCID 19008610, compound

60% Sodium hydride (1.0 g) was suspended in dimethylformamide (hereinafter abbreviated as DMF) (5 ml) and under ice-cooling, a DMF solution (5 ml) of ethyl 7-(2-chloro-4-trifluoromethylphenoxy)-3,4-dihydro-3-oxo-2H-1,4-benzoxazine-2-carboxylate (Compound 1) (0.8 g) was dropwise added thereto, followed by stirring for 10 minutes. Methyl iodide (0.4 g) was then added, the mixture was further stirred for 10 minutes, and to the reaction mixture was added water (20 ml) and the mixture was extracted twice with ethyl acetate (50 ml). The extract was washed with water and then saturated aqueous sodium chloride, and dried over magnesium sulfate. The solvent was then evaporated under a reduced pressure and the residue was purified by silica gel chromatography (eluant: n-hexane/ethyl acetate=3/1) to give 0.4 g of the title compound (colorless oil).

1. temperatureunder ice-cooling
2. stirringthe mixture was further stirred for 10 minutes
3. extractionthe mixture was extracted twice with ethyl acetate (50 ml)
4. washThe extract was washed with water
5. dry with materialsaturated aqueous sodium chloride, and dried over magnesium sulfate
6. customThe solvent was then evaporated under a reduced pressure
7. customthe residue was purified by silica gel chromatography (eluant: n-hexane/ethyl acetate=3/1)

ORD record

ord-24fef3739ba7443ca80f63544d05c527

Source dataset

uspto-grants-1994_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05338719