Acetonitrile → 1-(4-Methoxybenzyl)-4-nitro-1H-pyrazole

HRID 869073Notes

Reaction equation

HRID 869073 reaction equation
[N+:1]([C:4]1N=[CH:6][NH:7][CH:8]=1)([O-:3])=[O:2].C(Cl)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:17](=[O:20])([O-])[O-].[K+].[K+].[C:23](#[N:25])C>>[CH3:17][O:20][C:10]1[CH:15]=[CH:14][C:13]([CH2:6][N:7]2[CH:8]=[C:4]([N+:1]([O-:3])=[O:2])[CH:23]=[N:25]2)=[CH:12][CH:11]=1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 178526856HCID 178526856, compound

Product 1

HCID 666114661-(4-Methoxybenzyl)-4-nitro-1H-pyrazole

Procedure

A mixture of 4-nitro-imidazole (2.75 g, 24.3 mmol), benzyl chloride (4.3 g, 26.8 mmol), potassium carbonate (4 g, 29.2 mmol), and acetonitrile (50 mL) was stirred for 2 h at rt, warmed to 55° C., stirred for 16 h, allowed to cool to rt, concentrated, diluted with water, and extracted with EtOAc. The organic extracts were washed with brine, dried (Na2SO4), filtered, and concentrated. The residue was purified by silica gel column chromatography (hexane/EtOAc, 4:1) to afford 5.6 g of the title compound. tR: 0.93 min (LC-MS 4); ESI-MS: 234.3 [M+H]+ (LC-MS 4); Rf=0.25 (hexane/EtOAc, 4:1).

Workup

  1. temperaturewarmed to 55° C.
  2. stirringstirred for 16 h
  3. temperatureto cool to rt
  4. concentrationconcentrated
  5. additiondiluted with water
  6. extractionextracted with EtOAc
  7. washThe organic extracts were washed with brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was purified by silica gel column chromatography (hexane/EtOAc, 4:1)

Sources & evidence

ORD record
ord-8b1f5fef60af4d16b7c8635d67b28bbb
Source dataset
uspto-grants-2015_03
Patent number
US08969341B2

Reaction notes

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