Pyrazole → N,N-dimethyl-1H-pyrazole-1-sulfonamide

HRID 1409006Notes

Reaction equation

HRID 1409006 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][CH:5]=[N:4]1.[CH3:8][N:9]([CH3:14])[S:10](Cl)(=[O:12])=[O:11].C(=O)([O-])O.[Na+]>O1CCCC1>[CH3:8][N:9]([CH3:14])[S:10]([N:3]1[CH:7]=[CH:6][CH:5]=[N:4]1)(=[O:12])=[O:11]

Participants

6

Reactant 4

HCID 1048PyrazoleHCID 24758Sodium hydrideHCID 83372Dimethylsulphamoyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 10954038N,N-dimethyl-1H-pyrazole-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (50%, 8.46 g) was added to a solution of pyrazole (12 g) in tetrahydrofuran (200 mL) while stirring at 0° C. After 20 min, dimethylsulfamoyl chloride (17 mL) was added dropwise, and the mixture was stirred at the same temperature for 1 hr and allowed to warm to room temperature over 1 hr. The reaction system was poured into saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate, and dried over anhydrous magnesium sulfate. Insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (25.3 g) as a colorless oil.

Workup

  1. stirringthe mixture was stirred at the same temperature for 1 hr
  2. temperatureto warm to room temperature over 1 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customInsoluble material was removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-818b98a45c4b414b8441611e7effb045
Source dataset
uspto-grants-2014_12
Patent number
US08921354B2

Reaction notes

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