2-[(Methylthio)methyl]-4-(trifluoromethyl)benzenamine → 4-Amino-3-methylbenzotrifluoride

HRID 1391646Notes

Reaction equation

HRID 1391646 reaction equation
CS[CH2:3][C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:5]=1[NH2:14]>[Ni].C(O)C>[CH3:3][C:4]1[CH:9]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:7]=[CH:6][C:5]=1[NH2:14]

Participants

4

Reactant 1

HCID 98132532-[(Methylthio)methyl]-4-(trifluoromethyl)benzenamine

Product 1

HCID 137504374-Amino-3-methylbenzotrifluorideYield 85.9%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Activated Raney nickel (500 g wet paste, ˜50μ) was added portionwise to a solution of 2-[(methylthio)methyl]-4-(trifluoromethyl)benzenamine (55.3 g, 0.25 mole) in 1 L of ethanol over 30 minutes at 25-30° C. The heterogeneous mixture was stirred vigorously for 30 minutes after the addition. The stirring was stopped, and the solids were allowed to settle over one hour. The liquid was decanted from the solids and poured through filter paper. The filtrate was evaporated under reduced pressure, and the residue was taken up in dichloromethane. The organic phase was separated from a small volume of water, dried over magnesium sulfate and evaporated under reduced pressure to afford 37.6 g of the title compound as amber oil.

Workup

  1. additionafter the addition
  2. waitto settle over one hour
  3. customThe liquid was decanted from the solids
  4. additionpoured
  5. filtrationthrough filter paper
  6. customThe filtrate was evaporated under reduced pressure
  7. customThe organic phase was separated from a small volume of water
  8. dry with materialdried over magnesium sulfate
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-f38b37df819b41c1b701f182d93523e0
Source dataset
uspto-grants-2008_03
Patent number
US07338978B2

Reaction notes

Loading…