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

HRID 72774Notes

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

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

customThe reaction liquid
extractionextracted with diethyl ether
washThe organic layer was washed successively with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
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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