HCID 23359001, compound → HCID 23359007, compound

HRID 232647Notes

Reaction equation

HRID 232647 reaction equation
[F:1][C:2]1[C:8]([CH3:9])=[C:7]([F:10])[C:6]([F:11])=[C:5]([CH2:12]SC)[C:3]=1[NH2:4]>[Ni].C(O)C>[F:1][C:2]1[C:8]([CH3:9])=[C:7]([F:10])[C:6]([F:11])=[C:5]([CH3:12])[C:3]=1[NH2:4]

Participants

4

Reactant 1

HCID 23359001HCID 23359001, compound

Product 1

HCID 23359007HCID 23359007, compoundYield 69.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To 2,4,5-trifluoro-3-methyl-6-methylthiomethylaniline (10.67 g) are added ethanol (300 ml) and Raney nickel (100 g, wet) and the mixture is stirred at room temperature for 30 minutes. After Raney nickel is filtered off, the filtrate is concentrated, diluted with water, extracted with dichloromethane, and the extract is washed with water and dried. The solvent is distilled off under reduced pressure and the residue is purified by silica-gel column-chromatography (dichloromethane: n-hexane =1:1) to give 2,4,5-trifluoro-3,6-dimethylaniline (5.89 g), as yellow crystals.

Workup

  1. filtrationAfter Raney nickel is filtered off
  2. concentrationthe filtrate is concentrated
  3. additiondiluted with water
  4. extractionextracted with dichloromethane
  5. washthe extract is washed with water
  6. customdried
  7. distillationThe solvent is distilled off under reduced pressure
  8. customthe residue is purified by silica-gel column-chromatography (dichloromethane: n-hexane =1:1)

Sources & evidence

ORD record
ord-de76bd3b62474e8bb2457160fa994382
Source dataset
uspto-grants-1997_01
Patent number
US05591744

Reaction notes

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