Iodine → HCID 67547252, compound

HRID 2356751Notes

Reaction equation

HRID 2356751 reaction equation
[CH2:1]([C:3]1[NH:7][CH:6]=[N:5][C:4]=1[C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)[CH3:2].C([O-])(=O)C.[K+].[I:19]I.O>CO.C(OCC)(=O)C>[CH2:1]([C:3]1[NH:7][C:6]([I:19])=[N:5][C:4]=1[C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)[CH3:2]

Participants

7

Reactant 4

HCID 807IodineHCID 962WaterHCID 517044Potassium AcetateHCID 45120975HCID 45120975, compound

Product 1

HCID 67547252HCID 67547252, compoundYield 67.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-ethyl-4-(3-pyridyl)imidazole (1.50 g) and potassium acetate (2.55 g) in methanol (40 ml) was added iodine (2.86 g), and the mixture was stirred at room temperature overnight. To the reaction mixture were added water and ethyl acetate, and the organic layer was collected, washed with a saturated aqueous sodium thiosulfate solution and brine and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by NH silica gel flush column chromatography (solvent: ethyl acetate) to obtain 5-ethyl-2-iodo-4-(3-pyridyl)imidazole (1.75 g).

Workup

  1. customthe organic layer was collected
  2. washwashed with a saturated aqueous sodium thiosulfate solution and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe resulting residue was purified by NH silica gel
  6. customflush column chromatography (solvent: ethyl acetate)

Sources & evidence

ORD record
ord-1159d834f29b46ddb58f3c6319da2b0f
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

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