alpha,alpha,alpha-Trifluoro-3-nitro-4-(phenylthio)toluene → 2-(Phenylsulfanyl)-5-(trifluoromethyl)aniline

HRID 435713Notes

Reaction equation

HRID 435713 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:17]([F:20])([F:19])[F:18])[CH:7]=[CH:8][C:9]=1[S:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O-])=O>C(O)C.[Ni]>[NH2:1][C:4]1[CH:5]=[C:6]([C:17]([F:20])([F:18])[F:19])[CH:7]=[CH:8][C:9]=1[S:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 1

HCID 67667alpha,alpha,alpha-Trifluoro-3-nitro-4-(phenylthio)toluene

Product 1

HCID 125903632-(Phenylsulfanyl)-5-(trifluoromethyl)aniline

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

26.9 g of 3-nitro-4-(phenylthio)-benzotrifluoride in 250 ml of ethanol are hydrogenated in the presence of 10 g of Raney-nickel at room temperature and atmospheric pressure for 17 hours. The mixture is filtered and evaporated under reduced pressure. There is obtained 3-amino-4-(phenylthio)-benzotrifluoride as a red-brown oil. The compound is distilled under greatly reduced pressure and boils at 110°-135° C/0.1 mm; orange-coloured oil.

Workup

  1. filtrationThe mixture is filtered
  2. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-05f2fc180ce546d7bad93d597545d791
Source dataset
uspto-grants-1977_02
Patent number
US04006144

Reaction notes

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