Sodium Iodide → 1-(2-Methoxyethyl)-4-nitro-1H-pyrazole

HRID 1910387Notes

Reaction equation

HRID 1910387 reaction equation
[CH:1]1[NH:5][N:4]=[CH:3][C:2]=1[N+:6]([O-:8])=[O:7].[H-].[Na+].[CH3:11][O:12][CH2:13][CH2:14]Br.[Na+].[I-]>CN(C=O)C>[CH3:11][O:12][CH2:13][CH2:14][N:4]1[CH:3]=[C:2]([N+:6]([O-:8])=[O:7])[CH:1]=[N:5]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 163764-nitro-1H-pyrazoleHCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl ether

Product 1

HCID 578205541-(2-Methoxyethyl)-4-nitro-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-nitropyrrazole (2.0 g) in DMF was added NaH (60% dispersion in oil) under ice cooling. After stirring at the same temperature for 10 minutes, 2-bromoethyl methyl ether (2.00 ml) and NaI (2.92 g) was added. The mixture was then stirred at room temperature for 3 hours, quenched by phosphate buffer solution (pH=7) and extracted with EtOAc. The extract was washed with H2O and brine, dried over MgSO4, and evaporated in vacuo. The residue was purified by column chromatography on silica gel to give 1-(2-methoxyethyl)-4-nitro-1H-pyrazole (2.15 g).

Workup

  1. stirringThe mixture was then stirred at room temperature for 3 hours
  2. customquenched by phosphate buffer solution (pH=7)
  3. extractionextracted with EtOAc
  4. washThe extract was washed with H2O and brine
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-7851221c29f3480397c3a3f24fa0cdaa
Source dataset
uspto-grants-2013_12
Patent number
US08603975B2

Reaction notes

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