Pyridine → 4-[1-(1-Imidazolyl)-butyl]-benzonitrile

HRID 727844Notes

Reaction equation

HRID 727844 reaction equation
[N:1]1([CH:6]([C:10]2[CH:18]=[CH:17][C:13]([C:14]([NH2:16])=O)=[CH:12][CH:11]=2)[CH2:7][CH2:8][CH3:9])[CH:5]=[CH:4][N:3]=[CH:2]1.N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[N:1]1([CH:6]([C:10]2[CH:11]=[CH:12][C:13]([C:14]#[N:16])=[CH:17][CH:18]=2)[CH2:7][CH2:8][CH3:9])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 11430Potassium CarbonateHCID 145143674-[1-(1-Imidazolyl)-butyl]-benzamide

Product 1

HCID 145143624-[1-(1-Imidazolyl)-butyl]-benzonitrileYield 70.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
5 °C

Procedure

4.9 g of the amide of example 3 is dissolved in 50 ml of dioxane and 3.23 ml of pyridine and mixed with 3.16 ml of trifluoroacetic acid anhydride under ice cooled at 5° C. internal temperature. After 20 hours of stirring at room temperature it is added to half-saturated potassium carbonate solution, extracted with ether and the ether phase is dried and concentrated by evaporation. After distillation on a bulb tube at 200°-215° C./0.05 mbar, 3.2 g of 4-[1-(1-imidazolyl)-butyl]-benzonitrile is obtained, which, after crystallization from ether, melts at 63°-71° C.

Workup

  1. extractionextracted with ether
  2. dry with materialthe ether phase is dried
  3. concentrationconcentrated by evaporation
  4. distillationAfter distillation on a bulb tube at 200°-215° C./0.05 mbar

Sources & evidence

ORD record
ord-958aeea9d15a41b1bd57817014b6bf38
Source dataset
uspto-grants-1991_09
Patent number
US05045558

Reaction notes

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