Triethylamine → N,N-dimethyl-3-(trifluoromethyl)-1H-pyrazole-1-sulfonamide

HRID 238671Notes

Reaction equation

HRID 238671 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]1[CH:7]=[CH:6][NH:5][N:4]=1.C(N(CC)CC)C.[CH3:17][N:18]([CH3:23])[S:19](Cl)(=[O:21])=[O:20]>ClCCl.C(OCC)C>[CH3:17][N:18]([CH3:23])[S:19]([N:5]1[CH:6]=[CH:7][C:3]([C:2]([F:9])([F:8])[F:1])=[N:4]1)(=[O:21])=[O:20]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 83372Dimethylsulphamoyl chlorideHCID 18070343-(Trifluoromethyl)pyrazole

Product 1

HCID 66826467N,N-dimethyl-3-(trifluoromethyl)-1H-pyrazole-1-sulfonamideYield 99.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-trifluoromethylpyrazole (5.0 g, 36 mmol), triethylamine (7.0 mL, 50 mmol) in dichloromethane (40 mL) was added dimethylsulfamoyl chloride (5.5 mL, 51 mmol), and the reaction mixture was heated at reflux for 2 days. The resulting mixture was cooled to ambient temperature and filtered through a pad of silica gel using dichloromethane as eluent. The filtrate was then concentrated under reduced pressure to give an amber residue. The resulting residue was dissolved in diethyl ether. The ether solution was washed with water, dried (MgSO4), and concentrated under reduced pressure to give 8.71 g of the title compound.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 2 days
  3. filtrationfiltered through a pad of silica gel
  4. concentrationThe filtrate was then concentrated under reduced pressure
  5. customto give an amber residue
  6. washThe ether solution was washed with water
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b76b1bad2d0d4129aedbe7933402080a
Source dataset
uspto-grants-2014_02
Patent number
US08642634B2

Reaction notes

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