Triethylamine → 5-Chloro-3-phenylisoxazole
Reaction equation
P(Cl)(Cl)([Cl:3])=O.[C:6]1([C:12]2[NH:13][O:14][C:15](=O)[CH:16]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C>>[C:6]1([C:12]2[CH:16]=[C:15]([Cl:3])[O:14][N:13]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1Participants
Procedure
To 84.3 g (0.55 mol) of phosphorus oxychloride, 18.3 g (0.11 mol) of 3-phenyl-5-isoxazolone were added under stirring. While the internal temperature was maintained at 0°-10.C., 11.1 g (0.11 mol) of triethylamine were added further. They were then reacted under heating and stirring at 100°-120° C. for 3 hours. The reaction mixture was allowed to stand overnight at room temperature, and precipitated insoluble matter was filtered off. After the filtrate thus obtained was concentrated under reduced pressure, the residue was transferred into 500 ml of ice water, followed by neutralization with sodium hydrogencarbonate. The solution was extracted with ethyl ether. The organic layer was washed with water and then dried. The solvent was distilled off and the residue was purified by silica gel column chromatography (solvent: hexane/ethyl acetate=20/1), whereby the title compound was obtained as colorless crystals.
Workup
- customThey were then reacted
- temperatureunder heating
- stirringstirring at 100°-120° C. for 3 hours
- customprecipitated insoluble matter
- filtrationwas filtered off
- customAfter the filtrate thus obtained
- concentrationwas concentrated under reduced pressure
- extractionThe solution was extracted with ethyl ether
- washThe organic layer was washed with water
- customdried
- distillationThe solvent was distilled off
- customthe residue was purified by silica gel column chromatography (solvent: hexane/ethyl acetate=20/1), whereby the title compound
- customwas obtained as colorless crystals
Sources & evidence
- ORD record
- ord-2b8cb48b9f0d458ba2062ba1ff0ac972
- Source dataset
- uspto-grants-1992_05
- Patent number
- US05112841
Reaction notes
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