Potassium Carbonate → 1-(2-Chloro-5-methyl-3-pyridylmethyl)2-nitroiminoimidazolidine

HRID 413473

Reaction equation

HRID 413473 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8]Cl)=[CH:6][C:5]([CH3:10])=[CH:4][N:3]=1.[N+:11]([N:14]=[C:15]1[NH:19][CH2:18][CH2:17][NH:16]1)([O-:13])=[O:12].C(=O)([O-])[O-].[K+].[K+].[Cl-].[Cs+]>C(#N)C>[Cl:1][C:2]1[C:7]([CH2:8][N:16]2[CH2:17][CH2:18][NH:19][C:15]2=[N:14][N+:11]([O-:13])=[O:12])=[CH:6][C:5]([CH3:10])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 24293Cesium ChlorideHCID 112060822-Chloro-3-(chloromethyl)-5-methylpyridineHCID 135413413N-nitroimidazolidin-2-imine

Product 1

HCID 1363477121-(2-Chloro-5-methyl-3-pyridylmethyl)2-nitroiminoimidazolidineYield 90%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-chloro-3-chloromethyl-5-methylpyridine (1.3 g, 0.0076 moles) was added to a well-stirred material comprising 2-nitroimino-1, 3-diazacyclopentane (1.18 g, 0.00912 moles), potassium carbonate (1.16 g, 0.0083 moles), cesium chloride (0.04 g, 0.00024 moles) in acetonitrile (20 ml) solvent at room temperature. The reaction mixture was refluxed for 8 hours. The solvent was removed under reduced pressure and the mass diluted with water (25 ml). The mass was then extracted with methylene chloride (2×50 ml) and the layers were separated. Organic layer was dried over sodium sulphate and solvent removed under reduced pressure. The residue thus obtained was subjected to chromatographic purification on silica gel to give 1-(2-chloro-5-methyl-3-pyridylmethyl)2-nitroiminoimidazolidine in 90% yield.

Workup

  1. customat room temperature
  2. temperatureThe reaction mixture was refluxed for 8 hours
  3. customThe solvent was removed under reduced pressure
  4. additionthe mass diluted with water (25 ml)
  5. extractionThe mass was then extracted with methylene chloride (2×50 ml)
  6. customthe layers were separated
  7. dry with materialOrganic layer was dried over sodium sulphate and solvent
  8. customremoved under reduced pressure
  9. customThe residue thus obtained
  10. customwas subjected to chromatographic purification on silica gel

Sources & evidence

ORD record
ord-9e0e5b816c2f4bac938a2cceb69764b1
Source dataset
uspto-grants-2003_05
Patent number
US06566528B1

Linked notes

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