Iodoethane → 5-Chloro-1-ethyl-4-nitro-1H-pyrazole

HRID 1487670Notes

Reaction equation

HRID 1487670 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:7]=[N:8][NH:9][CH:10]=1)([O-:5])=[O:4].I[CH2:12][CH3:13].[Cl-:14].[NH4+]>CN(C=O)C>[Cl:14][C:10]1[N:9]([CH2:12][CH3:13])[N:8]=[CH:7][C:6]=1[N+:3]([O-:5])=[O:4]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 163764-nitro-1H-pyrazoleHCID 24758Sodium hydrideHCID 25517Ammonium Chloride

Product 1

HCID 584650475-Chloro-1-ethyl-4-nitro-1H-pyrazoleYield 82.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of sodium hydride (1 equiv, 60% in mineral oil) in DMF (0.64 M) under nitrogen atmosphere was added a solution of 4-nitro-1H-pyrazole (0.83 equiv) in DMF (3.2 M) at 0° C. The reaction mixture was stirred at room temperature for 30 min before a solution of iodoethane (1 equiv) in DMF (3.2 M) was added. The mixture was stirred at room temperature for 2 h. Saturated aqueous ammonium chloride solution (0.32 M) was added, and the solvent was removed under reduced pressure to give the crude product, which was purified by silica gel column chromatography (25% ethyl acetate in petroleum ether) to give the desire product (82.2% yield) as white solid. MS (ESI) m/z 142.0 [M+H]+.

Workup

  1. additionwas added
  2. customthe solvent was removed under reduced pressure
  3. customto give the crude product, which
  4. customwas purified by silica gel column chromatography (25% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-b38086195e534b44beb16add756a81e7
Source dataset
uspto-grants-2016_08
Patent number
US09428509B2

Reaction notes

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