Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Potassium bisulfate | HCID 516920 | — |
| Reactant | N-[(6-chloropyridin-3-yl)methyl]-2,2-difluoroethanamine | HCID 44604123 | — |
| Reactant | Methyl 4-hydroxy-2-oxo-2,5-dihydrofuran-3-carboxylate | HCID 54677706 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Butyronitrile | HCID 8008 | — |
| Product | Flupyradifurone | HCID 16752772 | 108.8% |
Reaction Steps
To a suspension of 5.2 g of 4-(methoxycarbonyl)-5-oxo-2,5-dihydrofuran-3-ol and 5 g of N-[(6-chloropyridin-3-yl)methyl]-2,2-difluoroethylamine in 70 ml of butyronitrile are added, at room temperature. 4.5 g of potassium hydrogensulphate. The mixture is stirred at a temperature of 120° C. for 3 hours. Subsequently, the mixture is cooled to room temperature and admixed with 60 ml of water and 60 ml of dichloromethane. The organic phase is removed and the aqueous phase is extracted twice with 30 ml each time of methylene chloride. The combined organic phases are concentrated to dryness. 7.6 g of 4-[[(6-chloropyridin-3-yl)methyl](2,2-difluoroethyl)amino]furan-2(5H)-one are obtained in a purity of 85% (this corresponds to 94% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08273904B2 |
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| Source dataset | uspto-grants-2012_09 |
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| ORD ID | ord-3dea7313f4c04233a58a8c7f5b04e2c2 |
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| Source note | uspto-grants-2012_09 |
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