Ethyl Acetate → 4-Chloro-3-(5-phenyl-1H-imidazol-2-yl) aniline

HRID 2077264Notes

Reaction equation

HRID 2077264 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[C:11]1[NH:12][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:14][N:15]=1.O.O.[Sn](Cl)Cl.C(OCC)(=O)C.[OH-].[Na+]>CCO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[C:11]1[NH:12][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:14][N:15]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 580065202-(2-chloro-5-nitrophenyl)-5-phenyl-1H-imidazole

Product 1

HCID 498408204-Chloro-3-(5-phenyl-1H-imidazol-2-yl) aniline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-(2-chloro-5-nitro-phenyl)-5-phenyl-1H-imidazole (430 mg, 1.43 mmol) and tin (II) chloride dihydrate (1.15 g, 5.02 mmol) in EtOH (15 ml) is heated at reflux for 3 hours. The mixture is cooled down to room temperature and the solvent is removed in vacuo. The residue obtained is treated with ethyl acetate (80 ml) and 1N NaOH solution is added until the pH is raised to around 12. The suspension is kept stirring for 10 minutes and then filtered through Celite cake. The solution obtained is concentrated to yield 4-chloro-3-(5-phenyl-1H-imidazol-2-yl)-phenylamine as a dark red foam-like solid.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 3 hours
  3. customthe solvent is removed in vacuo
  4. customThe residue obtained
  5. additionis added until the pH
  6. temperatureis raised to around 12
  7. filtrationfiltered through Celite cake
  8. customThe solution obtained
  9. concentrationis concentrated

Sources & evidence

ORD record
ord-2d146881697c4feb9f1eb6565fe18843
Source dataset
uspto-grants-2011_04
Patent number
US07928133B2

Reaction notes

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