Sodium Hydroxide → HCID 53942252, compound

HRID 1586763Notes

Reaction equation

HRID 1586763 reaction equation
Cl[C:2]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=1[Cl:20])([CH2:9][CH2:10][CH2:11][CH3:12])[CH2:3][N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1.[OH-].[Na+]>CS(C)=O>[Cl:20][C:14]1[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:13]=1[C:2]([CH2:9][CH2:10][CH2:11][CH3:12])=[CH:3][N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19759744HCID 19759744, compound

Product 1

HCID 53942252HCID 53942252, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 10 g of 1-[2-chloro-2-(2,4-dichlorophenyl)hexyl] imidazole in 100 ml of dimethyl sulfoxide is added 25 ml of 50% sodium hydroxide solution dropwise at room temperature. The reaction mixture is heated at 60° for 2 hours. It is then poured into 300 ml of ice water and extracted with ether. The combined ether extracts are washed with saturated sodium chloride solution and dried over magnesium sulfate. Drying agent is filered and to the filtrate is added concentrated nitric acid dropwise until it is strongly acidic. An oily material settled and is triturated with a 50--50 ether-hexane mixture three times and then back neutralized to its free base with 10% ammonium hydroxide solution. The free base is extracted with ether and the combined ether extracts are washed with water and saturated sodium chloride solution and dried over magnesium sulfate. Solvent is evaporated to give 6 g of a brown oily product.

Workup

  1. temperatureThe reaction mixture is heated at 60° for 2 hours
  2. extractionextracted with ether
  3. washThe combined ether extracts are washed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customDrying agent
  6. additionis added concentrated nitric acid dropwise until it
  7. customis triturated with a 50--50 ether-hexane mixture three times
  8. extractionThe free base is extracted with ether
  9. washthe combined ether extracts are washed with water and saturated sodium chloride solution
  10. dry with materialdried over magnesium sulfate
  11. customSolvent is evaporated

Sources & evidence

ORD record
ord-1966344532b64404a7003f86ca68a989
Source dataset
uspto-grants-1993_06
Patent number
US05216007

Reaction notes

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