Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Butyronitrile | HCID 8008 | — |
| Reactant | Potassium bisulfate | HCID 516920 | — |
| Reactant | N-[(6-chloropyridin-3-yl)methyl]-2,2-difluoroethanamine | HCID 44604123 | — |
| Product | Flupyradifurone | HCID 16752772 | 92% |
Reaction Steps
To a suspension of 10.4 g of potassium 4-(ethoxycarbonyl)-5-oxo-2,5-dihydrofuran-3-oxide and 7.5 g of N-[(6-chloropyridin-3-yl)methyl]-2,2-difluoroethylamine in 68 ml of butyronitrile are added, at room temperature, 11.5 g of potassium hydrogensulphate. The mixture is stirred at a temperature of 90 to 95° C. for 3 hours. Subsequently, the mixture is cooled to room temperature, 120 ml of water and 120 ml of dichloromethane are added, the organic phase is removed and the aqueous phase is extracted twice with 120 ml each time of methylene chloride. The combined organic phases are concentrated to dryness. 11.4 g of 4[[(6-chloropyridin-3-yl)methyl](2,2-difluoroethyl)amino]furan-2(5H)-one are obtained in a purity of 84% (this corresponds to 92% 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-e52ed903c29b4237bae5f5235977804e |
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| Source note | uspto-grants-2012_09 |
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