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

HRID 576861Notes

Reaction equation

HRID 576861 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

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 33.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
160 °C

Procedure

2,5-Dichloro-3-nitropyridine 100 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-57405b6668904f7688b880c56d7ce0b6
Source dataset
uspto-grants-2015_05
Patent number
US09040536B2

Reaction notes

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