2-Amino-3-(methylthiomethyl)benzotrifluoride → 2-Amino-3-methylbenzotrifluoride

HRID 326991Notes

Reaction equation

HRID 326991 reaction equation
CS[CH2:3][C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[C:5]=1[NH2:6]>[Ni].C(O)C>[CH3:3][C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:12])([F:13])[F:14])[C:5]=1[NH2:6]

Participants

4

Reactant 1

HCID 27359342-Amino-3-(methylthiomethyl)benzotrifluoride

Product 1

HCID 133182332-Amino-3-methylbenzotrifluorideYield 27.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 702EthanolSolvent

Procedure

Several scoops of Raney nickel were added to 28.6 g of 2-{(methylthio)methyl}-6-(trifluoromethyl)aniline (Example 1A) in 50 ml of absolute ethanol. The reaction slurry was stirred at room temperature and the progress of the reaction was followed by gas-liquid chromatography (GLC). Periodically, additional Raney nickel was added to the reaction slurry. The reaction was allowed to stir overnight. Most but not all of the starting material had reacted. The Raney nickel was removed by filtration, the filter cake rinsed with 1200 ml of absolute ethanol and the filtrate concentrated. The concentrate was dissolved in 100 ml of ethyl acetate, washed with 70 ml of water, dried with magnesium sulfate, filtered, and concentrated to yield 19.2 g of the crude product as a yellow oil which was distilled at 30-40 torr, to give 6.2 g of the desired product at 93°-108° C. in 80% purity.

Workup

  1. stirringto stir overnight
  2. customMost but not all of the starting material had reacted
  3. customThe Raney nickel was removed by filtration
  4. washthe filter cake rinsed with 1200 ml of absolute ethanol
  5. concentrationthe filtrate concentrated
  6. dissolutionThe concentrate was dissolved in 100 ml of ethyl acetate
  7. washwashed with 70 ml of water
  8. dry with materialdried with magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto yield 19.2 g of the crude product as a yellow oil which
  12. distillationwas distilled at 30-40 torr

Sources & evidence

ORD record
ord-dd547f27e5df4a0cbe83a7145f15d399
Source dataset
uspto-grants-1993_12
Patent number
US05272128

Reaction notes

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