1,3-Diiodopropane → 1,3-Bis[(6-chloronicotinyl)-2-nitroiminoimidazolidin-3-yl]propane

HRID 1813951Notes

Reaction equation

HRID 1813951 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:19]=[CH:18][C:7]([CH2:8][N:9]2[CH2:13][CH2:12][NH:11][C:10]2=[N:14][N+:15]([O-:17])=[O:16])=[CH:6][N:5]=1.I[CH2:21][CH2:22][CH2:23]I>CN(C=O)C>[Cl:3][C:4]1[CH:19]=[CH:18][C:7]([CH2:8][N:9]2[CH2:13][CH2:12][N:11]([CH2:21][CH2:22][CH2:23][N:11]3[CH2:12][CH2:13][N:9]([CH2:8][C:7]4[CH:18]=[CH:19][C:4]([Cl:3])=[N:5][CH:6]=4)[C:10]3=[N:14][N+:15]([O-:17])=[O:16])[C:10]2=[N:14][N+:15]([O-:17])=[O:16])=[CH:6][N:5]=1

Participants

6

Reactant 4

HCID 123141,3-DiiodopropaneHCID 24758Sodium hydrideHCID 86287518ImidaclopridHCID 1355277641-[(6-chloropyridin-3-yl)methyl]-N-nitroimidazolidin-2-imine

Product 1

HCID 737062891,3-Bis[(6-chloronicotinyl)-2-nitroiminoimidazolidin-3-yl]propane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (60% oil dispersion, 0.17 g, 4.25 mmol) was suspended in 10 ml of DMF. 1-(6-Chloronicotinyl)-2-nitroiminoimidazolidine (1.03 g, 4 mmol), which is commonly referred to as imidacloprid), was added to this suspension. This mixture was then stirred for 1 hour at room temperature. A solution of 1,3-diiodopropane (0.58 g, 2 mmol) in DMF (10 ml) was then added dropwise to this reaction mixture over the course of 30 minutes while cooling with ice. Following completion of dropping, the reaction mixture was stirred at room temperature for 4 hours.

Workup

  1. additionwas added to this suspension
  2. temperaturewhile cooling with ice
  3. stirringthe reaction mixture was stirred at room temperature for 4 hours

Sources & evidence

ORD record
ord-df47b182e7cc4d1b8c2f82b58842e3bb
Source dataset
uspto-grants-2005_04
Patent number
US06875778B2

Reaction notes

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