Iodine → N-(4-iodo-1H-pyrazol-5-yl)acetamide

HRID 1615702Notes

Reaction equation

HRID 1615702 reaction equation
[NH:1]1[C:5]([NH:6][C:7](=[O:9])[CH3:8])=[CH:4][CH:3]=[N:2]1.[I:10](O)(=O)=O.II>C(O)C>[I:10][C:4]1[CH:3]=[N:2][NH:1][C:5]=1[NH:6][C:7](=[O:9])[CH3:8]

Participants

5

Reactant 3

HCID 807IodineHCID 24345Iodic acidHCID 27775273-Acetylaminopyrazole

Product 1

HCID 86717260N-(4-iodo-1H-pyrazol-5-yl)acetamideYield 348.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of N-(1H-pyrazol-5-yl)acetamide (60 g, 0.48 mol), iodic acid (21.1 g, 0.12 mol) and iodine (61 g, 0.24 mol) in ethanol (1.6 L) was heated at 60° C. for 1.5 h and cooled to room temperature. The reaction mixture was concentrated in vacuo and partitioned between ethyl acetate and 2 M Na2S2O3 aq. solution. The layers were separated and the aqueous extracted with ethyl acetate. The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo to provide the title compound as a solid (105 g).

Workup

  1. temperaturecooled to room temperature
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. custompartitioned between ethyl acetate and 2 M Na2S2O3 aq. solution
  4. customThe layers were separated
  5. extractionthe aqueous extracted with ethyl acetate
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d3d30bc4b9954565895fa88ee2f52698
Source dataset
uspto-grants-2014_07
Patent number
US08765762B2

Reaction notes

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