Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Ethyl Bromide | HCID 6332 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 86748071 | HCID 86748071 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 54002352 | HCID 54002352 | 94.1% |
Reaction Steps
To a DMF (10 ml) solution of 7-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-2,4-dimethyl-2-[1(hydroxyimino)ethyl]-3,4-dihydro-3-oxo-2H-1,4-benzoxazine (Compound 101) (0.3 g) obtained in Example 16 was added, under ice-cooling, 60% sodium hydride (0.03 g), and after stirring for 20 minutes, bromoethane (0.1 g) was dropwise added thereto. After stirring for 2 hours, 1N hydrochloric acid was added and the mixture extracted twice with ethyl acetate (20 ml). The extract was then washed with water and with saturated aqueous sodium chloride, and dried over magnesium sulfate. The solvent was evaporated under a reduced pressure, and the residue purified by silica gel chromatography (eluant: n-hexane/ethyl acetate=4/1) to give 0.3 g of the title compound (colorless oil).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05338719 |
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| Source dataset | uspto-grants-1994_08 |
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| ORD ID | ord-cf87f0f7e4f543a5bc3fbaba4e5d8c1d |
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| Source note | uspto-grants-1994_08 |
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