Sodium hydride → HCID 86617144, compound

HRID 2243276Notes

Reaction equation

HRID 2243276 reaction equation
[H-].[Na+].[CH3:3][N:4]1[C:8]([C:9]([F:15])([F:14])[C:10]([F:13])([F:12])[F:11])=[N:7][N:6]=[C:5]1[SH:16].[H][H].F[C:20]1[CH:21]=[CH:22][C:23]([N+:27]([O-:29])=[O:28])=[C:24]([CH3:26])[CH:25]=1>CN(C=O)C>[CH3:3][N:4]1[C:8]([C:9]([F:14])([F:15])[C:10]([F:11])([F:12])[F:13])=[N:7][N:6]=[C:5]1[S:16][C:20]1[CH:21]=[CH:22][C:23]([N+:27]([O-:29])=[O:28])=[C:24]([CH3:26])[CH:25]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 949565-Fluoro-2-nitrotolueneHCID 178418361HCID 178418361, compoundHCID 178481703HCID 178481703, compound

Product 1

HCID 86617144HCID 86617144, compoundYield 49.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.10 g) was added to a DMF solution (12 ml) of 4-methyl-5-pentafluoroethyl-4H-[1,2,4]triazol-3-thiol (0.70 g), and the mixture was stirred at room temperature until the generation of hydrogen gas stopped. Continuously, 5-fluoro-2-nitrotoluene (0.47 g) was added thereto and the mixture was further stirred at room temperature for 1 hour. After cooling to room temperature, the reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride and then dried with anhydrous sodium sulfate. After distilling off the solvent, the obtained residue was purified by silica gel column chromatography (mixed solvent of n-hexane and ethyl acetate) to obtain the aimed 4-methyl-3-(3-methyl-4-nitrophenyl sulfanyl)-5-pentafluoroethyl-4H-(1,2,4)-triazole (0.55 g).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  4. dry with materialdried with anhydrous sodium sulfate
  5. distillationAfter distilling off the solvent
  6. customthe obtained residue was purified by silica gel column chromatography (mixed solvent of n-hexane and ethyl acetate)

Sources & evidence

ORD record
ord-3f0d5affd7084ba4b168ff8d5e280f93
Source dataset
uspto-grants-2010_03
Patent number
US07674807B2

Reaction notes

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