Iodoethane → 1-Ethyl-4-nitro-1H-pyrazole

HRID 2375846Notes

Reaction equation

HRID 2375846 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].I[CH2:16][CH3:17]>CN(C)C=O.CCOC(C)=O>[CH2:16]([N:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:8]=[N:7]1)[CH3:17]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 163764-nitro-1H-pyrazole

Product 1

HCID 125652131-Ethyl-4-nitro-1H-pyrazole

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-nitro-1H-pyrazole (226 mg, 2.0 mmol) in N,N-dimethylformamide (3 mL) were added potassium carbonate (0.33 g, 2.4 mmol) and iodoethane (0.37 g, 2.4 mmol). The resulting mixture was stirred at rt overnight. TLC showed the reaction was complete. The mixture was diluted with EtOAc (40 mL), then washed with water (2×20 mL), brine (20 mL), and dried over anhydrous sodium sulfate. The crude material was purified by chromatography on silica gel, eluting with Hex:EtOAc=70:30 to give the title compound as a white solid. 1H NMR (CDCl3, 400 MHz): δ=1.55 (t, J=7.3 Hz, 3H), 4.22 (q, J=7.3 Hz, 2H), 8.07 (s, 1H), 8.14 (s, 1H).

Workup

  1. washwashed with water (2×20 mL), brine (20 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe crude material was purified by chromatography on silica gel
  4. washeluting with Hex

Sources & evidence

ORD record
ord-d04ced4490c54fc288a28c841127d9a7
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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