Hydrochloric Acid → HCID 178478329, compound

HRID 1881861Notes

Reaction equation

HRID 1881861 reaction equation
[OH-].[Na+].[I:3][C:4]1[NH:8][C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[N:6][CH:5]=1.[ClH:15]>Cl([O-])=O.[Na+]>[Cl:15][C:5]1[N:6]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[NH:8][C:4]=1[I:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59331526HCID 59331526, compound

Product 1

HCID 178478329HCID 178478329, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 23668197Sodium ChloriteSolvent

Procedure

To 5% aqueous sodium chlorite solution (180 mL) was added sodium hydroxide (737 mg) and completely dissolved. To the reaction solution was added 2-(5-iodo-1H-imidazol-2-yl)pyridine (5.00 g), and the mixture was stirred at room temperature for 24 hr. The reaction mixture was adjusted to pH 3 to 4 with 1M hydrochloric acid, 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 basic silica gel column chromatography (ethyl acetate:hexane=30:70-100:0, volume ratio) to give the title compound (3.57 g, yield 63%) as colorless crystals. melting point 188-189° C.

Workup

  1. dissolutioncompletely dissolved
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=30:70-100:0, volume ratio)

Sources & evidence

ORD record
ord-e5d3133366ae4f8aaef155d9e048a870
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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