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Sodium Iodide → 5-Chloro-2-(2-cyclohexyl-1H-imidazol-1-yl)-3-nitropyridine

HRID 72774
Notes
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Reaction equation

HRID 72774 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([Cl:11])=[CH:4][N:3]=1.[CH:12]1([C:18]2[NH:19][CH:20]=[CH:21][N:22]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.[I-].[Na+]>CN(C)C=O>[Cl:11][C:5]1[CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]([N:19]2[CH:20]=[CH:21][N:22]=[C:18]2[CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[N:3][CH:4]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 80633312,5-Dichloro-3-nitropyridineHCID 111594052-Cyclohexyl-1H-imidazole

Product 1

HCID 591985595-Chloro-2-(2-cyclohexyl-1H-imidazol-1-yl)-3-nitropyridineYield 67.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
160 °C

Procedure

2,5-Dichloro-3-nitropyridine 1.00 g, 2-cyclohexylimidazole 1.56 g, sodium iodide 500 mg and N,N-dimethylformamide 25 mL were mixed and stirred at 160° C. for 15.5 hours. The reaction liquid was poured in ice water and extracted with diethyl ether. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. Distilling the solvent off under reduced pressure, the residue was subjected to silica gel chromatography (hexane:ethyl acetate=2:1) to provide 1.08 g of the title compound.

Workup

  1. customThe reaction liquid
  2. extractionextracted with diethyl ether
  3. washThe organic layer was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationDistilling the solvent off under reduced pressure

Sources & evidence

ORD record
ord-5e7066b4ceae4b46abd3fd926db85860
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08829000B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes