Water → (1-tert-butyl-5-chloro-3-trifluoromethyl-1H-pyrazol-4-yl)-methanethiol

HRID 1292796Notes

Reaction equation

HRID 1292796 reaction equation
Br[CH2:2][C:3]1[C:4]([C:13]([F:16])([F:15])[F:14])=[N:5][N:6]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:7]=1[Cl:8].O.[SH-:18].[Na+].O>CN(C)C=O>[C:9]([N:6]1[C:7]([Cl:8])=[C:3]([CH2:2][SH:18])[C:4]([C:13]([F:16])([F:15])[F:14])=[N:5]1)([CH3:12])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 962WaterHCID 16211346Sodium hydrosulfide hydrateHCID 178628684-bromomethyl-1-tert-butyl-5-chloro-3-trifluoromethyl-1H-pyrazole

Product 1

HCID 17862846(1-tert-butyl-5-chloro-3-trifluoromethyl-1H-pyrazol-4-yl)-methanethiolYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

43.5 g (136.1 mmoles) of 4-bromomethyl-1-tert-butyl-5-chloro-3-trifluoromethyl-1H-pyrazole was added to a solution of 21.8 g of sodium hydrosulfide hydrate (purity: 70%, 272.2 mmoles) dissolved in 300 ml of N,N-dimethylformamide. The mixture was stirred at room temperature overnight to give rise to a reaction. After the completion of the reaction, the reaction mixture was poured into water, followed by extraction with diethyl ether. The resulting organic layer was washed with an aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to vacuum distillation to remove the solvent contained therein, to obtain 32.3 g (yield: 87.0%) of (1-tert-butyl-5-chloro-3-trifluoromethyl-1H-pyrazol-4-yl)-methanethiol.

Workup

  1. customto give rise
  2. customto a reaction
  3. customAfter the completion of the reaction
  4. extractionfollowed by extraction with diethyl ether
  5. washThe resulting organic layer was washed with an aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe resulting solution was subjected to vacuum distillation
  8. customto remove the solvent

Sources & evidence

ORD record
ord-706adff0e52f4083a8bb0f38c2042c58
Source dataset
uspto-grants-2007_07
Patent number
US07238689B2

Reaction notes

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