HCID 12692632, compound → 14453-85-1

HRID 1792746Notes

Reaction equation

HRID 1792746 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=2)=[CH:5][CH:4]=1>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([S:9][C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2)=[CH:7][CH:8]=1

Participants

3

Reactant 1

HCID 12692632HCID 12692632, compound

Product 1

HCID 1233797814453-85-1Yield 68.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 13.06 g of 4-(4-methoxy-phenylsulfanyl)-nitrobenzene from step 1 in 100 mL of ethanol was added 33.85 g of SnCl2−2H2O. The resulting mixture was stirred for 30 minutes at room temperature, then heated to reflux for 2 hours. The mixture was then cooled to room temperature, concentrated in vacuo, and treated with 20% aqueous NaOH. The solution was extracted three times with ethyl acetate, and the combined extracts were washed with water followed by brine, dried (MgSO4), after which the ethyl acetate was removed in vacuo. The resulting solid was chromatographed on SiO2 (70%/30% dichloromethane/hexanes) to afford 7.87 g (68%) of 4-(4-methoxy-phenylsulfanyl)-phenylamine. Mp: 91–92° C. MS M+H: 232.

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. temperatureThe mixture was then cooled to room temperature
  4. concentrationconcentrated in vacuo
  5. additiontreated with 20% aqueous NaOH
  6. extractionThe solution was extracted three times with ethyl acetate
  7. washthe combined extracts were washed with water
  8. dry with materialdried (MgSO4)
  9. customafter which the ethyl acetate was removed in vacuo
  10. customThe resulting solid was chromatographed on SiO2 (70%/30% dichloromethane/hexanes)

Sources & evidence

ORD record
ord-9dd4fd30ac414a2e8efe65060324f68e
Source dataset
uspto-grants-2006_07
Patent number
US07078401B2

Reaction notes

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