4-Chloro-2-nitro-1-(phenylthio)benzene → 5-Chloro-2-phenylsulfanyl-phenylamine

HRID 2399373Notes

Reaction equation

HRID 2399373 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:4]([N+:15]([O-])=O)[CH:3]=1.[H][H]>[Ni].C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:4]([NH2:15])[CH:3]=1

Participants

5

Reactant 2

HCID 3769774-Chloro-2-nitro-1-(phenylthio)benzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 20637175-Chloro-2-phenylsulfanyl-phenylamineYield 88.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of 4-chloro-2-nitro-1-(phenylthio)benzene (11.0 g) and Raney nickel in ethanol (3A; 9.3 mL) was reacted in a Parr Hydrogenator under hydrogen atmosphere at 5 psi and room temperature. When the theoretical amount of hydrogen uptake was reached, the reaction was filtered to remove the catalyst and evaporated in vacuo to yield 8.61 g (88%) of a light orange solid. mp: 59°-61° C.

Workup

  1. filtrationthe reaction was filtered
  2. customto remove the catalyst
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-cdf47578dafe4651a43501bc9198d941
Source dataset
uspto-grants-1995_09
Patent number
US05449675

Reaction notes

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