Potassium Carbonate → N,N-dimethyl-2-(4-nitro-1H-pyrazol-1-yl)acetamide

HRID 1968525Notes

Reaction equation

HRID 1968525 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].Cl[CH2:10][C:11]([N:13]([CH3:15])[CH3:14])=[O:12].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:14][N:13]([CH3:15])[C:11](=[O:12])[CH2:10][N:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:8]=[N:7]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 163764-nitro-1H-pyrazoleHCID 758862-chloro-N,N-dimethylacetamide

Product 1

HCID 60729245N,N-dimethyl-2-(4-nitro-1H-pyrazol-1-yl)acetamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 4-nitro-1H-pyrazole (0.4 g, 3.54 mmol), 2-chloro-N,N-dimethylacetamide (0.546 ml, 5.31 mmol) and potassium carbonate (0.733 g, 5.31 mmol) in 18 ml acetone was refluxed for 6 hours. The cooled suspension was filtered with acetone washes and the concentrated residue was flash chromatographed (50 mm, 3% methanol in CH2Cl2) to afford the title compound.

Workup

  1. temperaturewas refluxed for 6 hours
  2. filtrationThe cooled suspension was filtered with acetone washes
  3. customchromatographed (50 mm, 3% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-6311ee7d652a40a7b61b4583e234d152
Source dataset
uspto-grants-2013_04
Patent number
US08426408B2

Reaction notes

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