4-(3,5-Dimethyl-benzylsulfanyl)-nitrobenzene → 4-(3,5-Dimethyl-benzylsulfanyl)-phenylamine

HRID 855994Notes

Reaction equation

HRID 855994 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([CH3:19])[CH:18]=1)[CH2:5][S:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=1>O.C(O)C.[Fe]>[CH3:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([CH3:19])[CH:18]=1)[CH2:5][S:6][C:7]1[CH:8]=[CH:9][C:10]([NH2:13])=[CH:11][CH:12]=1

Participants

5

Reactant 1

HCID 694205454-(3,5-Dimethyl-benzylsulfanyl)-nitrobenzene

Product 1

HCID 432993384-(3,5-Dimethyl-benzylsulfanyl)-phenylamineYield 93.1%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 4-(3,5-dimethyl-benzylsulfanyl)-nitrobenzene (0.35 g, 1.28 mmol) calcium chloride (0.071 g, 0.64 mmol) and iron powder (−325 mesh) (0.573 g, 10.3 mmol) in 4 ml water and 17 ml ethanol was heated at reflux under nitrogen for 4.5 h. The reaction mixture was then cooled to room temperature, filtered through Celite and the filtrate was concentrated under reduced pressure. The residual oil was purified by column chromatography, eluting with 9:1 hexane/ethyl acetate to yield the title compound as a yellowish oil (0.29 g, 91% yield). MS: 244.3 (M+1)

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 4.5 h
  3. filtrationfiltered through Celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residual oil was purified by column chromatography
  6. washeluting with 9:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-fa9e83e4ee6544528f789f601c7bcb73
Source dataset
uspto-grants-2007_08
Patent number
US07262318B2

Reaction notes

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