Ethanesulfonyl chloride → HCID 67189366, compound

HRID 546045Notes

Reaction equation

HRID 546045 reaction equation
[N+:1]([C:4]1[CH:8]=[CH:7][NH:6][N:5]=1)([O-:3])=[O:2].[H-].[Na+].[CH2:11]([S:13](Cl)(=[O:15])=[O:14])[CH3:12]>CN(C)C=O.C(OCC)(=O)C>[CH2:11]([S:13]([N:6]1[CH:7]=[CH:8][C:4]([N+:1]([O-:3])=[O:2])=[N:5]1)(=[O:15])=[O:14])[CH3:12]

Participants

6

Reactant 3

HCID 11667Ethanesulfonyl chlorideHCID 24758Sodium hydrideHCID 178526745HCID 178526745, compound

Product 1

HCID 67189366HCID 67189366, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Nitro-1H-pyrazole (prepared in example 3, 100 mg, 0.89 mmol) was dissolved in anhydrous N,N-dimethylformamide (4 mL) and a 60% dispersion of sodium hydride in mineral oil (39 mg, 0.94 mmol) was added while stirring under nitrogen. After the effervescence ceased and the mixture was stirred for an additional 10 min, the ethanesulfonyl chloride (94 μL, 1.00 mmol) was added. The mixture was continued to stir under nitrogen for 16 h. The solution was diluted with ethyl acetate (50 mL), washed with water (2×20 mL), saturated aqueous brine solution (2×20 mL), dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by ISCO flash column chromatography (Teledyne Isco RediSep Flash Column 10 g; 25% ethyl acetate/hexanes to 75% ethyl acetate/hexanes) afforded 1-ethanesulfonyl-3-nitro-1H-pyrazole (139 mg, 77%) as a clear, waxy solid: H1-NMR (400 MHz, CDCl3) δ 1.38 (2H, t, J=7.2 Hz), 3.68 (2H, qt, J=7.2 Hz), 7.05 (1H, d, J=2.8 Hz), 8.14 (1H, d, J=2.8 Hz).

Workup

  1. stirringthe mixture was stirred for an additional 10 min
  2. stirringto stir under nitrogen for 16 h
  3. washwashed with water (2×20 mL), saturated aqueous brine solution (2×20 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by ISCO flash column chromatography (Teledyne Isco RediSep Flash Column 10 g; 25% ethyl acetate/hexanes to 75% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-2d18bf0da3bf4c4f84da16c7709394e7
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

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