Iodine → HCID 178474491, compound

HRID 2205776Notes

Reaction equation

HRID 2205776 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([NH:7][C:8](=[O:10])[CH3:9])[NH:4][N:3]=1.[I:11](O)(=O)=O.II>C(O)C>[I:11][C:6]1[C:2]([CH3:1])=[N:3][NH:4][C:5]=1[NH:7][C:8](=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 807IodineHCID 24345Iodic acidHCID 178474264HCID 178474264, compound

Product 1

HCID 178474491HCID 178474491, compoundYield 231.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of N-(3-methyl-1H-pyrazol-5-yl)acetamide (29.6 g, 0.213 mol), iodic acid (9.3 g, 0.053 mol) and iodine (32.5 g, 0.128 mol) in ethanol (300 mL) was heated at 50° C. for 3 h and cooled to room temperature. The reaction mixture was concentrated in vacuo and taken up in ethyl acetate. The solution was washed twice with 2 M Na2S2O3 followed by brine solution. The organic layer was dried (magnesium sulphate), filtered and concentrated in vacuo. The residue was triturated from diethyl ether, filtered and dried to provide the title compound as a white solid (32.5 g).

Workup

  1. temperaturecooled to room temperature
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. washThe solution was washed twice with 2 M Na2S2O3
  4. dry with materialThe organic layer was dried (magnesium sulphate)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated from diethyl ether
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-8c7281da230d4e2d99c69d9bce5579e2
Source dataset
uspto-grants-2016_06
Patent number
US09371332B2

Reaction notes

Loading…