p-Fluoronitrobenzene → HCID 20282214, compound

HRID 463291Notes

Reaction equation

HRID 463291 reaction equation
[CH3:1][C:2]([CH3:12])([CH3:11])[CH:3]([OH:10])[CH2:4][N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1.[H-].[Na+].[H][H].F[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1>CN(C)C=O.C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[N+:24]([C:21]1[CH:22]=[CH:23][C:18]([O:10][CH:3]([C:2]([CH3:12])([CH3:11])[CH3:1])[CH2:4][N:5]2[CH:9]=[CH:8][N:7]=[CH:6]2)=[CH:19][CH:20]=1)([O-:26])=[O:25]

Participants

8

Reactant 4

HCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 13457359HCID 13457359, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20282214HCID 20282214, compoundYield 72.7%

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(3,3-dimethyl-2-hydroxy-n-butyl)imidazole (5.2 g) in a mixture of 50 ml of dimethylformamide and 25 ml of toluene was treated with sodium hydride (3.4 g of 50% dispersion in mineral oil) and stirred at room temperature. After the evolution of hydrogen ceases, manganese dioxide (3.0 g) was added and the mixture cooled in an ice bath. To this mixture was added p-fluoronitrobenzene (8.0 g) and the resulting mixture stirred at room temperature for 3 hours. The reaction mixture was then filtered through Celite washing the residue with toluene, and the filtrate washed several times with water. The toluene layer was separated and dried over sodium sulfate, and evaporated to give yellow crystals. After trituration with ether, the resulting solid was chromatographed on silica gel eluting with 5% methanol in methylene chloride. The resulting product was recrystallized from ethyl acetate to give 6.5 g of 1-[2-(4-nitrophenoxy)-3,3-dimethyl-n-butyl]imidazole.

Workup

  1. temperaturethe mixture cooled in an ice bath
  2. stirringthe resulting mixture stirred at room temperature for 3 hours
  3. filtrationThe reaction mixture was then filtered through Celite
  4. washwashing the residue with toluene
  5. washthe filtrate washed several times with water
  6. customThe toluene layer was separated
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customto give yellow crystals
  10. customAfter trituration with ether, the resulting solid was chromatographed on silica gel eluting with 5% methanol in methylene chloride
  11. customThe resulting product was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-62d909252cb44a6db66587e9453b0bf2
Source dataset
uspto-grants-1985_05
Patent number
US04518607

Reaction notes

Loading…