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

HRID 254216

Reaction equation

HRID 254216 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].CN(C)C=O.O.[SH-:23].[Na+]>C(OCC)C>[C:9]([N:6]1[C:7]([Cl:8])=[C:3]([CH2:2][SH:23])[C:4]([C:13]([F:16])([F:15])[F:14])=[N:5]1)([CH3:12])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 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 3283Diethyl EtherSolvent

Procedure

43.5 g (136.1 mmoles) of 4-bromomethyl-1-tert-butyl-5-chloro-3-trifluoromethyl-1H-pyrazole was added to 300 ml of a N,N-dimethylformamide solution containing 21.8 g (272.2 mmoles) of sodium hydrosulfide hydrate (purity: 70%). 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 ice water and extraction with diethyl ether was conducted. 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 reduced pressure 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)-metha-nethiol.

Workup

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

Sources & evidence

ORD record
ord-0139c3b7b01d469282f5458362306b2c
Source dataset
uspto-grants-2011_01
Patent number
US07875606B2

Linked notes

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