Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Potassium bisulfate | HCID 516920 | — |
| Reactant | 4-(Ethoxycarbonyl)-5-oxo-2,5-dihydrofuran-3-olate potassium salt | HCID 44604122 | — |
| Reactant | N-[(6-chloropyridin-3-yl)methyl]-2,2-difluoroethanamine | HCID 44604123 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Butyronitrile | HCID 8008 | — |
| Product | Flupyradifurone | HCID 16752772 | 92% |
Reaction Steps
At room temperature, 11.5 g of potassium bisulphate are added to a suspension of 10.4 g of 4-(ethoxycarbonyl)-5-oxo-2,5-dihydrofuran-3-olate potassium salt and 7.5 g of N-[(6-chloropyridin-3-yl)methyl)-2,2-difluoroethylamine in 68 ml of butyronitrile. The mixture is stirred at a temperature of from 90 to 95° C. for 3 hours. The mixture is then cooled to room temperature, 120 ml of water and 120 ml of dichloromethane are added, the organic phase is separated off and the aqueous phase is extracted twice with in each case 120 ml of methylene chloride. The combined organic phases are concentrated to dryness. This gives 11.4 g of amorphous 4-[[(6-chloropyridin-3-yl)methyl](2,2-difluoroethyl)amino]furan-2(5H)-one in a purity of 84% (this corresponds to a yield of 92%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08476448B2 |
|---|
| Source dataset | uspto-grants-2013_07 |
|---|
| ORD ID | ord-475f8c4e064547feb0f1b6fed618a6a3 |
|---|
| Source note | uspto-grants-2013_07 |
|---|