Iodine → ethyl 2-(5-acetamido-4-iodo-3-phenyl-1H-pyrazol-1-yl)acetate

HRID 2205824Notes

Reaction equation

HRID 2205824 reaction equation
[C:1]([NH:4][C:5]1[N:9]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:8]=[C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:6]=1)(=[O:3])[CH3:2].[I:22](O)(=O)=O.II>C(O)C>[C:1]([NH:4][C:5]1[N:9]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:8]=[C:7]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:6]=1[I:22])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 807IodineHCID 24345Iodic acidHCID 86717316ethyl 2-(5-acetamido-3-phenyl-1H-pyrazol-1-yl)acetate

Product 1

HCID 86717317ethyl 2-(5-acetamido-4-iodo-3-phenyl-1H-pyrazol-1-yl)acetateYield 352.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of ethyl 2-(5-acetamido-3-phenyl-pyrazol-1-yl)acetate (34.81 g, 60.6 mmol), iodic acid (5.33 g, 30.3 mmol) and iodine (15.37 g, 60.6 mmol) in ethanol (250 mL) was heated at 50° C. for 1.5 h and cooled to room temperature. The reaction mixture was concentrated in vacuo and the residue was dissolved in CH2Cl2 (250 mL). 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 solid (44.13 g).

Workup

  1. temperaturecooled to room temperature
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionthe residue was dissolved in CH2Cl2 (250 mL)
  4. washThe solution was washed twice with 2 M Na2S2O3
  5. dry with materialThe organic layer was dried (magnesium sulphate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was triturated from diethyl ether
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-87b9eef60b0f4b99a98579326a5a4263
Source dataset
uspto-grants-2016_06
Patent number
US09371332B2

Reaction notes

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