Ethanol → 5-Chloro-2-(2-isopropyl-1H-imidazol-1-yl)aniline

HRID 72756Notes

Reaction equation

HRID 72756 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][N:10]=[C:9]2[CH:13]([CH3:15])[CH3:14])=[C:4]([N+:16]([O-])=O)[CH:3]=1.O.O.[Sn](Cl)Cl.C(O)C.[OH-].[Na+]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][N:10]=[C:9]2[CH:13]([CH3:15])[CH3:14])=[C:4]([CH:3]=1)[NH2:16]

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 591988521-(4-Chloro-2-nitrophenyl)-2-isopropyl-1H-imidazole

Product 1

HCID 285030025-Chloro-2-(2-isopropyl-1H-imidazol-1-yl)aniline

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 1-(4-chloro-2-nitrophenyl)-2-isopropyl-1H-imidazole as synthesized in above Production Example 7, 0.98 g, tin (II) chloride dihydrate 4.16 g and ethanol 8.8 mL was heated under reflux for 2.7 hours. Neutralizing the reaction liquid with 2N aqueous sodium hydroxide solution under cooling with ice, chloroform was added to the reaction liquid and filtered through Celite. The Celite was washed with chloroform, transferred into a separating funnel and extracted twice with chloroform. The organic layer was washed with water, dried over magnesium sulfate and removed of the solvent by distillation, to provide 0.72 g of the title compound.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2.7 hours
  3. additionwas added to the reaction liquid
  4. filtrationfiltered through Celite
  5. washThe Celite was washed with chloroform
  6. customtransferred into a separating funnel
  7. extractionextracted twice with chloroform
  8. washThe organic layer was washed with water
  9. dry with materialdried over magnesium sulfate
  10. customremoved of the solvent by distillation

Sources & evidence

ORD record
ord-a7fbf30874e1438182610be0e9b8dbee
Source dataset
uspto-grants-2014_09
Patent number
US08829000B2

Reaction notes

Loading…