Iodine → N-(3-(2-chlorophenyl)-4-iodo-1-methyl-1H-pyrazol-5-yl)acetamide

HRID 1775510Notes

Reaction equation

HRID 1775510 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:12]=[C:11]([NH:13][C:14](=[O:16])[CH3:15])[N:10]([CH3:17])[N:9]=1.[I:18](O)(=O)=O.II>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:12]([I:18])=[C:11]([NH:13][C:14](=[O:16])[CH3:15])[N:10]([CH3:17])[N:9]=1

Participants

5

Reactant 3

HCID 807IodineHCID 24345Iodic acidHCID 70983638N-(3-(2-chlorophenyl)-1-methyl-1H-pyrazol-5-yl)acetamide

Product 1

HCID 70983478N-(3-(2-chlorophenyl)-4-iodo-1-methyl-1H-pyrazol-5-yl)acetamideYield 379.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of N-(3-(2-chlorophenyl)-1-methyl-1H-pyrazol-5-yl)acetamide (526 mg, 2.12 mmol) in ethanol (16 mL) were added iodic acid (93 mg, 0.53 mmol) and iodine (294 mg, 1.16 mmol). The reaction was stirred for 18 h at 50° C. The reaction mixture was concentrated in vacuo and the residue was dissolved in CH2Cl2 and washed with a 2 N Na2SO3 solution. The organic phase was dried over MgSO4, filtered and evaporated to give N-(3-(2-chlorophenyl)-4-iodo-1-methyl-1H-pyrazol-5-yl)acetamide as a light orange solid (756 mg), which was used as such in the subsequent step.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in CH2Cl2
  3. washwashed with a 2 N Na2SO3 solution
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-fc042e7884f1438384d543ab080c0842
Source dataset
uspto-grants-2016_02
Patent number
US09260381B2

Reaction notes

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