Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Dimethylacetamide | HCID 31374 | — |
| Reactant | Azane;hydrate | HCID 12896473 | — |
| Reactant | HCID 71615482 | HCID 71615482 | — |
| Catalyst | Zinc cyanide (Zn(CN)2) | HCID 11186 | — |
| Catalyst | Tetrakis(triphenylphosphine)palladium | HCID 11979704 | — |
| Product | HCID 86631560 | HCID 86631560 | — |
Reaction Steps
In a solution of 1.40 g of 5-(3,5-dichlorophenyl)-3-(5,6-dichloro-3-pyridyl)-5-trifluoromethyl-4,5-dihydroisoxazole in 30 mL of N,N-dimethylacetamide, 0.075 g of zinc cyanide and 0.37 g of tetrakis(triphenylphosphine) palladium(0) were added, and stirred at 80° C. to 120° C. for 4.5 hours under nitrogen atmosphere. After the completion of the reaction, the reaction mixture was left and cooled to room temperature, 5 mL of ammonia water and 50 mL of water were added, and extracted with ethyl acetate (50 mL×1). The organic phase were dehydrated with and dried over saturated sodium chloride aqueous solution and anhydrous magnesium sulfate in that order, and the solvent was distilled off under reduced pressure. The residue was purified with medium pressure preparative liquid chromatography (medium pressure collection apparatus: YFLC-Wprep manufactured by Yamazen Corporation) that was eluted with ethyl acetate-hexane (gradient of 1:8 to 1:3) to obtain 1.20 g of the aimed products as yellow resinous substance.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08242283B2 |
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| Source dataset | uspto-grants-2012_08 |
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| ORD ID | ord-690f3503e8af43fd886e83e5d48e3268 |
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| Source note | uspto-grants-2012_08 |
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