Potassium bisulfate → Flupyradifurone

HRID 1879318Notes

Reaction equation

HRID 1879318 reaction equation
S([O-])(O)(=O)=O.[K+].CN(C)[C:9]1[CH2:13][O:12][C:11](=[O:14])[CH:10]=1.[Cl:16][C:17]1[N:22]=[CH:21][C:20]([CH2:23][NH:24][CH2:25][CH:26]([F:28])[F:27])=[CH:19][CH:18]=1>C(#N)CCC>[Cl:16][C:17]1[N:22]=[CH:21][C:20]([CH2:23][N:24]([CH2:25][CH:26]([F:28])[F:27])[C:9]2[CH2:13][O:12][C:11](=[O:14])[CH:10]=2)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 516920Potassium bisulfateHCID 44604123N-[(6-chloropyridin-3-yl)methyl]-2,2-difluoroethanamineHCID 532593114-(Dimethylamino)-2(5H)-furanone

Product 1

HCID 16752772FlupyradifuroneYield 85.9%

Reagents, catalysts & solvents 1

HCID 8008ButyronitrileSolvent

Procedure

3.9 g of potassium hydrogen sulphate are added at room temperature to a suspension of 4.1 g of 4-(dimethylamino)furan-2(5H)-one and 5 g of N-[(6-chloropyridin-3-yl)methyl]-2,2-difluoroethylamine in 50 ml of butyronitrile. The mixture is refluxed for 8 h. Thereafter, cooling at room temperature and washing twice with 50 ml of water are effected. The solvent is removed in vacuo. 6 g of 4-[[(6-chloropyridin-3-yl)methyl](2,2-difluoroethyl)amino]furan-2(5H)-one are obtained with a purity of 92% (82% yield).

Workup

  1. temperatureThe mixture is refluxed for 8 h
  2. washwashing twice with 50 ml of water
  3. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-047227c7c8fa405288e1bbb85bf0c2ea
Source dataset
uspto-grants-2012_11
Patent number
US08314242B2

Reaction notes

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