1-Chloro-3-nitro-2-(propan-2-ylsulfanyl)benzene → 3-Chloro-2-(isopropylthio)aniline

HRID 363247Notes

Reaction equation

HRID 363247 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-])=O)[C:3]=1[S:11][CH:12]([CH3:14])[CH3:13].[H][H]>[Ni].CO>[NH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[S:11][CH:12]([CH3:14])[CH3:13]

Participants

5

Reactant 2

HCID 28232471-Chloro-3-nitro-2-(propan-2-ylsulfanyl)benzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 27357473-Chloro-2-(isopropylthio)aniline

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

40 g of 2-chloro-6-nitrophenyl-isopropylsulfane, 160 g of methanol and 2.4 g of Raney nickel 37-1 (methanol-moist) were initially introduced into a 0.7 l steel autoclave. After rinsing with nitrogen, 70 bar of hydrogen were forced in and the contents of the autoclave were heated to 100° C., while stirring. The hydrogen pressure was increased to 80 bar. After 50 minutes, the uptake of hydrogen had ended. The mixture was kept under the reaction conditions for a further 30 minutes. After cooling, letting down the hydrogen and removing the catalyst, the solvent was distilled off. Crude 2-amino-6-chlorophenyl-isopropylsulfane was already obtained as a 99% pure product (GC) which contained only 0.2% of 2-aminophenyl-isopropylsulfane (formed by dechlorination) and only 0.3% of m-chloroaniline (formed by desulfurization). The yield was 34.5 g.

Workup

  1. washAfter rinsing with nitrogen, 70 bar of hydrogen
  2. temperatureThe hydrogen pressure was increased to 80 bar
  3. customThe mixture was kept under the reaction conditions for a further 30 minutes
  4. temperatureAfter cooling
  5. customremoving the catalyst
  6. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-882c40b6950644b090fbbb8efdcdb21e
Source dataset
uspto-grants-1999_02
Patent number
US05872300

Reaction notes

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