Sodium Carbonate → 4-iodo-1-isopropyl-3-(4-methyl-2-thienyl)-1H-pyrazole

HRID 2359099Notes

Reaction equation

HRID 2359099 reaction equation
[CH:1]([N:4]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][CH:11]=[C:12]([CH3:14])[CH:13]=2)=[N:5]1)([CH3:3])[CH3:2].[I:15]N1C(=O)CCC1=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[I:15][C:7]1[C:6]([C:9]2[S:10][CH:11]=[C:12]([CH3:14])[CH:13]=2)=[N:5][N:4]([CH:1]([CH3:3])[CH3:2])[CH:8]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 24477Sodium ThiosulfateHCID 120273N-IodosuccinimideHCID 672617111-isopropyl-3-(4-methyl-2-thienyl)-1H-pyrazole

Product 1

HCID 672621804-iodo-1-isopropyl-3-(4-methyl-2-thienyl)-1H-pyrazoleYield 82.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-isopropyl-3-(4-methyl-2-thienyl)-1H-pyrazole (5.6 mmol) in 16 mL dry N,N-dimethylformamide under argon atmosphere was added N-iodosuccinimide (5.8 mmol) in small portions at 0° C. The reaction mixture was allowed to warm to room temperature and was stirred overnight. 5% aqueous sodium thiosulfate solution and saturated aqueous sodium carbonate solution were added and the mixture was stirred at room temperature for 1 h, then extracted with MTBE. The combined organic extracts were successively washed with water and brine, dried over MgSO4, filtered and concentrated. The residue was purified by chromatography on silica gel (cyclohexane:dichloromethane 100:0 to 0:100) to afford 1.54 g 4-iodo-1-isopropyl-3-(4-methyl-2-thienyl)-1H-pyrazole (82% yield).

Workup

  1. stirringthe mixture was stirred at room temperature for 1 h
  2. extractionextracted with MTBE
  3. washThe combined organic extracts were successively washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel (cyclohexane:dichloromethane 100:0 to 0:100)

Sources & evidence

ORD record
ord-946bd354208a4ceeafa0bac6ad91b50e
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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