Water → Flupyradifurone

HRID 446046Notes

Reaction equation

S(=O)(=O)(O)[O-].[K+].[K+].C(OC([C:13]1[C:17](=[O:18])[O:16][CH2:15][C:14]=1[O-])=O)C.[Cl:20][C:21]1[N:26]=[CH:25][C:24]([CH2:27][NH:28][CH2:29][CH:30]([F:32])[F:31])=[CH:23][CH:22]=1.O>C(#N)CCC.ClCCl>[Cl:20][C:21]1[N:26]=[CH:25][C:24]([CH2:27][N:28]([CH2:29][CH:30]([F:32])[F:31])[C:14]2[CH2:15][O:16][C:17](=[O:18])[CH:13]=2)=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 92.5 °C

Procedure

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%).

Workup

temperatureThe mixture is then cooled to room temperature
customthe organic phase is separated off
extractionthe aqueous phase is extracted twice with in each case 120 ml of methylene chloride
concentrationThe combined organic phases are concentrated to dryness

Sources & evidence

ORD record: ord-475f8c4e064547feb0f1b6fed618a6a3
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08476448B2

Reaction notes

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