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

HRID 1615728Notes

Reaction equation

HRID 1615728 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 325.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of ethyl 2-(5-acetamido-3-phenyl-pyrazol-1-yl)acetate (37 g, 129 mmol), iodic acid (5.6 g, 32 mmol) and iodine (19.7 g, 77 mmol) in ethanol (400 mL) was heated at 50° C. for 2 h and cooled to room temperature. The reaction mixture was concentrated in vacuo and the residue was eluted through a pad of silica gel with CH2Cl2 diethyl ether (1:0 to 97:3). The residue was partitioned between CH2Cl2 and 2 M Na2S2O3 aq. solution. The layers were separated and the organic washed was dried (MgSO4), and concentrated in vacuo to provide a residue that was partially purified by chromatography (silica gel, CH2Cl2/isohexane 1:1 to 1:0, then CH2Cl2/diethyl ether 9:1 to 8:2), then triturated with diethyl ether to provide the title compound as an off-white solid (43 g).

Workup

  1. temperaturecooled to room temperature
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. washthe residue was eluted through a pad of silica gel with CH2Cl2 diethyl ether (1:0 to 97:3)
  4. customThe residue was partitioned between CH2Cl2 and 2 M Na2S2O3 aq. solution
  5. customThe layers were separated
  6. washthe organic washed
  7. dry with materialwas dried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customto provide a residue that
  10. customwas partially purified by chromatography (silica gel, CH2Cl2/isohexane 1:1 to 1:0
  11. customCH2Cl2/diethyl ether 9:1 to 8:2), then triturated with diethyl ether

Sources & evidence

ORD record
ord-215da535a12743e3b925e963b17b8da1
Source dataset
uspto-grants-2014_07
Patent number
US08765762B2

Reaction notes

Loading…