Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Dicyclohexylamine | HCID 7582 | — |
| Reactant | Methyl bromoacetate | HCID 60984 | — |
| Reactant | HCID 19008591 | HCID 19008591 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 19008614 | HCID 19008614 | 63.9% |
Reaction Steps
7-(2-Chloro-4-trifluoromethylphenoxy)-2,4-dimethyl-3,4-dihydro-3-oxo-2H-1,4-benzoxazine-2-carboxylic acid (Compound 23) (0.4 g) was dissolved in DMF (0.2 ml) and dicyclohexylamine (0.2 ml) was added thereto, followed by stirring at 60° C. for 15 minutes. Then methyl bromoacetate (0.2 g) was added, the mixture further stirred at 60° C. for 3 hours, to the reaction mixture was added water (20 ml), and the mixture was extracted twice with ethyl acetate (20 ml). The extract was washed with water and then with saturated aqueous sodium chloride, and then dried over magnesium sulfate, followed by an evaporation of the solvent under a reduced pressure. The residue was purified by silica gel chromatography (eluant: n-hexane/ethyl acetate=3/1) to give 0.3 g of the title compound (colorless crystals).
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-7bda6d6ffd494f74bde421b8416f2385 |
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| Source note | uspto-grants-1994_08 |
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