Sulfur → 4-(Methylsulfanyl)-2-(trifluoromethyl)aniline

HRID 1973173Notes

Reaction equation

HRID 1973173 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10][CH3:11])=[CH:6][C:5]=1[C:12]([F:15])([F:14])[F:13])([O-])=O.[H][H].[S]>C(O)C.[Ni]>[CH3:11][S:10][C:7]1[CH:8]=[CH:9][C:4]([NH2:1])=[C:5]([C:12]([F:13])([F:14])[F:15])[CH:6]=1

Participants

6

Reactant 3

HCID 5362487SulfurHCID 22768209HCID 22768209, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 130700554-(Methylsulfanyl)-2-(trifluoromethyl)aniline

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

2-Nitro-5-methylthiobenzotrifluoride (190 g, 0.85 mole) in ethanol (1 l.) is reduced over Raney nickel at about 45 psi of hydrogen gas. After hydrogen uptake is complete the catalyst is deactivated with elemental sulfur, the mixture is filtered, and the filtrate evaporated under reduced pressure to afford the desired product as an oil. IR 2.9 μ (strong NH band).

Workup

  1. filtrationthe mixture is filtered
  2. customthe filtrate evaporated under reduced pressure

Sources & evidence

ORD record
ord-fa15c1c88f54447a99996e4dc0495744
Source dataset
uspto-grants-1976_12
Patent number
US03996277

Reaction notes

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