Stannous Chloride → 1,4-Benzenediamine, N1,N1-bis(4-aminophenyl)-

HRID 2180872Notes

Reaction equation

HRID 2180872 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]([C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[CH:22][CH:21]=2)[C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)=[CH:6][CH:5]=1)([O-])=O.[Sn](Cl)Cl>Cl>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([N:10]([C:20]2[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=2)[C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 88538Benzenamine, 4-nitro-N,N-bis(4-nitrophenyl)-

Product 1

HCID 800831,4-Benzenediamine, N1,N1-bis(4-aminophenyl)-Yield 99.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Tris(4-nitrophenyl)amine (1.9 g) was suspended in 6 N hydrochloric acid (80 ml), and then tin dichloride (31.3 g) was added at room temperature and the mixture was heated to reflux for one day. After cooling, the reaction solution was filtered, and 6 N sodium hydroxide (160 ml) was added to the filtrate while cooling on ice. The mixture was extracted twice with dichloromethane (200 mL). The organic layer was collected and dried over sodium sulfate, and then concentrated to obtain 1.44 g of the title compound as a brown powder (quantitative yield).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for one day
  3. temperatureAfter cooling
  4. filtrationthe reaction solution was filtered
  5. addition6 N sodium hydroxide (160 ml) was added to the filtrate
  6. temperaturewhile cooling on ice
  7. extractionThe mixture was extracted twice with dichloromethane (200 mL)
  8. customThe organic layer was collected
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-d43bd9a291b44567824a43b05eeda780
Source dataset
uspto-grants-2005_05
Patent number
US06887890B2

Reaction notes

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