Iodine → HCID 178474489, compound

HRID 588614Notes

Reaction equation

HRID 588614 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:12]=[C:11]([NH:13][C:14](=[O:16])[CH3:15])[NH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.[I:17](O)(=O)=O.II>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:12]([I:17])=[C:11]([NH:13][C:14](=[O:16])[CH3:15])[NH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 807IodineHCID 24345Iodic acidHCID 178474038HCID 178474038, compound

Product 1

HCID 178474489HCID 178474489, compoundYield 368.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of N-[3-(3-fluorophenyl)-1H-pyrazol-5-yl]acetamide (7.6 g, 34.7 mmol), iodic acid (1.5 g, 8.5 mmol) and iodine (4.4 g, 17.3 mmol) in ethanol (200 mL) was heated at 60° C. for 1 h and cooled to room temperature. The reaction mixture was concentrated in vacuo and partitioned between CH2Cl2 and 2 M Na2S2O3 aq. solution. The layers were separated and the organic washed with brine, dried (MgSO4), and concentrated in vacuo to provide the title compound as a solid (10.8 g).

Workup

  1. temperaturecooled to room temperature
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. custompartitioned between CH2Cl2 and 2 M Na2S2O3 aq. solution
  4. customThe layers were separated
  5. washthe organic washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e0a58e14d88c4772b337fbad60fd3375
Source dataset
uspto-grants-2016_01
Patent number
US09227976B2

Reaction notes

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