Potassium Carbonate → 1,4-Bis[(6-chloronicotinyl)-2-nitroiminoimidazolidin-3-yl]-2-butene

HRID 1813952Notes

Reaction equation

HRID 1813952 reaction equation
[CH:1]1[C:6]([CH2:7][N:8]2[CH2:9][CH2:10][NH:11]/[C:12]/2=[N:13]\[N+:14]([O-:16])=[O:15])=[CH:5][N:4]=[C:3]([Cl:17])[CH:2]=1.Br[CH2:19][CH:20]=[CH:21][CH2:22]Br.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:17][C:3]1[CH:2]=[CH:1][C:6]([CH2:7][N:8]2[CH2:9][CH2:10][N:11]([CH2:19][CH:20]=[CH:21][CH2:22][N:11]3[CH2:10][CH2:9][N:8]([CH2:7][C:6]4[CH:1]=[CH:2][C:3]([Cl:17])=[N:4][CH:5]=4)[C:12]3=[N:13][N+:14]([O-:16])=[O:15])[C:12]2=[N:13][N+:14]([O-:16])=[O:15])=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 131802-Butene, 1,4-dibromo-HCID 86287518Imidacloprid

Product 1

HCID 865902791,4-Bis[(6-chloronicotinyl)-2-nitroiminoimidazolidin-3-yl]-2-butene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Imidacloprid (3.37 g, 12 mmol), 1,4-dibromo-2-butene (1.60 g, 6 mmol), and potassium carbonate (1.83 g, 12 mmol) were mixed in 30 ml of acetonitrile, and the mixture was refluxed for 19 hours. After distilling off the solvent under reduced pressure, the residue was extracted with chloroform, and the chloroform layer was dried over magnesium sulfate. After distilling off the solvent, the residue was then subjected to silica gel column chromatography with a mixed solvent of ethyl acetate and ethanol (15:1 (v/v)) as the eluate. The crude product was purified by recrystallizing from ethanol. The yield of crystalline product was 0.22 g (7%), and the melting point was 199 to 202° C. The results of elementary analysis and NMR analysis are shown below.

Workup

  1. temperaturethe mixture was refluxed for 19 hours
  2. distillationAfter distilling off the solvent under reduced pressure
  3. extractionthe residue was extracted with chloroform
  4. dry with materialthe chloroform layer was dried over magnesium sulfate
  5. distillationAfter distilling off the solvent
  6. customThe crude product was purified
  7. customby recrystallizing from ethanol
  8. customThe results of elementary analysis and NMR analysis

Sources & evidence

ORD record
ord-64ca1fc1bf6546ffaaf9b2261deb3b34
Source dataset
uspto-grants-2005_04
Patent number
US06875778B2

Reaction notes

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