Iodine → N-(2-acetyl-4-iodo-5-phenyl-pyrazol-3-yl)acetamide

HRID 2205797Notes

Reaction equation

HRID 2205797 reaction equation
[C:1]([N:4]1[C:8]([NH:9][C:10](=[O:12])[CH3:11])=[CH:7][C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:5]1)(=[O:3])[CH3:2].[I:19](O)(=O)=O.II>C(O)C>[C:1]([N:4]1[C:8]([NH:9][C:10](=[O:12])[CH3:11])=[C:7]([I:19])[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 807IodineHCID 24345Iodic acidHCID 86717295N-(2-acetyl-5-phenyl-pyrazol-3-yl)acetamide

Product 1

HCID 86717296N-(2-acetyl-4-iodo-5-phenyl-pyrazol-3-yl)acetamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of N-(2-acetyl-5-phenyl-pyrazol-3-yl)acetamide (25.1 g, 0.103 mol), iodic acid (4.5 g, 0.026 mol) and iodine (15.7 g, 0.062 mol) in ethanol (250 mL) was heated at 50° C. for 3 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 (phase separator cartridge), and concentrated in vacuo to provide a mixture of the title compound and starting material (2.2:1, 30.3 g). The mixture was put in reaction again using iodic acid (1.6 g, 9.6 mmol) and iodine (9.7 g, 0.038 mol) in ethanol (250 mL) under the same conditions, to provide the title compound as a solid (31.9 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. customdried (phase separator cartridge)
  7. concentrationconcentrated in vacuo
  8. customto provide

Sources & evidence

ORD record
ord-844d2f02caa64f28b860e6709278155a
Source dataset
uspto-grants-2016_06
Patent number
US09371332B2

Reaction notes

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