Iodine → HCID 14743030, compound

HRID 747693

Reaction equation

HRID 747693 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.II.[I:21]([O-])(=O)=O.[Na+].I([O-])(=O)(=O)=O.[Na+]>C(O)(=O)C>[I:21][C:5]1[CH:4]=[CH:3][C:2]([CH2:1][C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)=[CH:7][CH:6]=1

Participants

7

Reactant 5

HCID 807IodineHCID 1118Sulfuric AcidHCID 164584-BenzylpyridineHCID 23667635Sodium periodateHCID 23675764Sodium Iodate

Product 1

HCID 14743030HCID 14743030, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5.0 g (30 mmol) of 4-benzylpyridine was dissolved in 30 ml of acetic acid. 3.53 ml (65 mmol) of concentrated sulfuric acid, 2.99 g (11.8 mmol) of iodine and 1.17 g (5.9 mmol) of sodium iodate were added to the solution, and the resultant mixture was stirred at 70° C. for 20 hours. After cooling, 0.15 g of sodium metaperiodate was added to the reaction mixture. After the distillation under reduced pressure, water was added to the residue, which was washed with dichloromethane. After the addition of 1 N aqueous sodium hydroxide solution followed by the extraction with dichloromethane twice, the solvent was evaporated. The residue was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. temperatureAfter cooling
  2. distillationAfter the distillation under reduced pressure, water
  3. additionwas added to the residue, which
  4. washwas washed with dichloromethane
  5. additionAfter the addition of 1 N aqueous sodium hydroxide solution
  6. extractionfollowed by the extraction with dichloromethane twice
  7. customthe solvent was evaporated
  8. customThe residue was purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-cbdd96963f104d08869b85dddfa470eb
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Linked notes

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