4-Toluenesulfonyl chloride → 1-(toluene-4-sulfonyl)-1H-pyrazole-3-carbaldehyde

HRID 1698221Notes

Reaction equation

HRID 1698221 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([CH:6]=[O:7])=[N:2]1.[H-].[Na+].[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1>C1COCC1.O>[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16]([N:1]2[CH:5]=[CH:4][C:3]([CH:6]=[O:7])=[N:2]2)(=[O:18])=[O:17])=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 122183831H-Pyrazole-3-carbaldehyde

Product 1

HCID 592783701-(toluene-4-sulfonyl)-1H-pyrazole-3-carbaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1H-pyrazole-3-carbaldehyde (3.00 g, 31.22 mmol) in THF was added 60% NaH (1.64 g, 41.00 mmol) in mineral oil. After 20 minutes, p-toluenesulfonyl chloride (7.82 g, 41.00 mmol) was added. After 2 hours, the reaction was diluted with water and extracted with EtOAc. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with a gradient of 10-50% EtOAc in heptane. The major fractions were combined and the solvent was concentrated in vacuo to afford (1-(toluene-4-sulfonyl)-1H-pyrazole-3-carbaldehyde) as a white solid.

Workup

  1. waitAfter 2 hours
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with a gradient of 10-50% EtOAc in heptane
  8. concentrationthe solvent was concentrated in vacuo

Sources & evidence

ORD record
ord-4a1b5cbe56c44c109afb5c7c41484341
Source dataset
uspto-grants-2012_04
Patent number
US08163918B2

Reaction notes

Loading…