Potassium Carbonate → Imidacloprid

HRID 1503201Notes

Reaction equation

HRID 1503201 reaction equation
[N+:1]([N:4]=[C:5]1[NH:9][CH2:8][CH2:7][NH:6]1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23]Cl)=[CH:19][N:18]=1>C(#N)C>[CH:21]1[C:20]([CH2:23][N:6]2[CH2:7][CH2:8][NH:9]/[C:5]/2=[N:4]\[N+:1]([O-:3])=[O:2])=[CH:19][N:18]=[C:17]([Cl:16])[CH:22]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1554792-Chloro-5-(chloromethyl)pyridine2×HCID 135413413N-nitroimidazolidin-2-imine2×

Product 1

HCID 86287518Imidacloprid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

7.8 g (60 mmol) of 2-nitroiminoimidazolidine and 12.1 g (87.5 mmol) of potassium carbonate were dissolved in 60 ml of acetonitrile in a reflux flask. The mixture is heated to a temperature sufficient for achieving reflux operating condition. 8.1 g (50.0 mole) of 2-chloro-5-chloromethyl pyridine is dissolved in 40 ml of acetonitrile, and is dropwisely and continuously added into the flask under the reflux condition for a period of 0.5 hr, i.e. the addition rate is about 1.5 ml/minute (the addition rate at the onset of the reaction corresponds to 0.0278 equivalent of 2-chloro-5-chloromethyl pyridine per equivalent of 2-nitroiminoimidazolidine per minute) After completion of the reaction, the mixture is subjected to filtration. The filtrate is concentrated, and is further purified.

Workup

  1. temperatureThe mixture is heated to a temperature sufficient
  2. temperaturefor achieving reflux
  3. additioncontinuously added into the flask under the reflux condition for a period of 0.5 hr
  4. customAfter completion of the reaction
  5. filtrationthe mixture is subjected to filtration
  6. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-eee6d67c3a054d1c8417c5071cd8bdb9
Source dataset
uspto-grants-2015_12
Patent number
US09212162B1

Reaction notes

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