Dimethylformamide → HCID 59331526, compound

HRID 1881860Notes

Reaction equation

HRID 1881860 reaction equation
[I:1][C:2]1[N:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[NH:5][C:6]=1I.CN(C)C=O.S([O-])([O-])=O.[Na+].[Na+]>O>[I:1][C:2]1[NH:3][C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[N:5][CH:6]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24437Sodium SulfiteHCID 59331430HCID 59331430, compound

Product 1

HCID 59331526HCID 59331526, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
120 °C

Procedure

To a solution of 2-(4,5-diiodo-1H-imidazol-2-yl)pyridine (18.6 g) in a mixed solvent of N,N-dimethylformamide (200 mL) and water (100 ml) was added sodium sulfite (35.4 g), and the mixture was stirred at 120° C. for 24 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:99-20:80, volume ratio) to give the title compound (11.2 g, yield 88%) as colorless crystals. melting point 175-179° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed successively with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:99-20:80, volume ratio)

Sources & evidence

ORD record
ord-fc69744d7e0c41b8b006aaef2c7bd677
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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