1-[1-(4-Bromophenyl)-butyl]-imidazole → 4-[1-(1-Imidazolyl)-butyl]-benzonitrile

HRID 727845Notes

Reaction equation

HRID 727845 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)[CH2:9][CH2:10][CH3:11])=[CH:4][CH:3]=1.[Cu][C:18]#[N:19]>CN1CCCC1>[N:12]1([CH:8]([C:5]2[CH:6]=[CH:7][C:2]([C:18]#[N:19])=[CH:3][CH:4]=2)[CH2:9][CH2:10][CH3:11])[CH:16]=[CH:15][N:14]=[CH:13]1

Participants

4

Reactant 2

HCID 145143611-[1-(4-Bromophenyl)-butyl]-imidazoleHCID 178418546HCID 178418546, compound

Product 1

HCID 145143624-[1-(1-Imidazolyl)-butyl]-benzonitrileYield 68.4%

Reagents, catalysts & solvents 1

HCID 84541-MethylpyrrolidineSolvent

Procedure

2.79 g of 1-[1-(4-bromophenyl)-butyl]-imidazole and 1.8 g of copper(I) cyanide are heated in 5 ml of N-methylpyrrolidine for 4 hours at 180° C. under a protecting gas atmosphere (argon). After cooling, it is precipitated in 50 ml of ammonia solution, stirred for 15 more minutes at room temperature and extracted with ethyl acetate. After concentration by evaporation in a vacuum 1.95 g of dark oil is obtained. This oil is distilled on a bulb tube in a vacuum; boiling point 200°-215° C./0.05 mbar. The resulting distillate is recrystallized from ethanol/petroleum ether. 1.54 g of 4-[1-(1-imidazolyl)-butyl]-benzonitrile with a melting point of 63°-71° C. is obtained.

Workup

  1. temperatureAfter cooling
  2. customit is precipitated in 50 ml of ammonia solution
  3. extractionextracted with ethyl acetate
  4. concentrationAfter concentration
  5. customby evaporation in a vacuum 1.95 g of dark oil
  6. customis obtained
  7. distillationThis oil is distilled on a bulb tube in a vacuum
  8. customThe resulting distillate is recrystallized from ethanol/petroleum ether

Sources & evidence

ORD record
ord-39a1a68327464ac18d2e006432f27dd7
Source dataset
uspto-grants-1991_09
Patent number
US05045558

Reaction notes

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