Water → Flupyradifurone

HRID 2190266Notes

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-344c925e40d64bcf80cafc045f79cb6c
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324392B2

Reaction notes

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