Potassium Iodide → 4-[1-(1,2,3-Triazolyl)methyl]-benzonitrile

HRID 483801Notes

Reaction equation

HRID 483801 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[N:2]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Br[CH2:15][C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=1>CC(C)=O>[NH:1]1[CH:5]=[C:4]([CH2:15][C:16]2[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=2)[N:3]=[N:2]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 869964-(Bromomethyl)benzonitrileHCID 178418936HCID 178418936, compound

Product 1

HCID 1785097034-[1-(1,2,3-Triazolyl)methyl]-benzonitrile

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

8 g of 1,2,3-triazole, 10.67 g of potassium carbonate and 750 mg of potassium iodide are added in succession to a solution of 15.13 g of 4-bromomethylbenzonitrile in 375 ml of acetone. The reaction mixture is then stirred at 55° for 7.5 hours, and is then cooled and concentrated. The residue is dissolved in CH2Cl2 and washed in succession with water and brine. After drying over sodium sulfate, the solution is concentrated and the resulting crude product is purified by column chromatography (SiO2, toluene/ethyl acetate 3:19) to yield the precursor (1), IR (CH2Cl2): 2230, 1615, 1225, 1075 cm-1.

Workup

  1. temperatureis then cooled
  2. concentrationconcentrated
  3. dissolutionThe residue is dissolved in CH2Cl2
  4. washwashed in succession with water and brine
  5. dry with materialAfter drying over sodium sulfate
  6. concentrationthe solution is concentrated
  7. customthe resulting crude product is purified by column chromatography (SiO2, toluene/ethyl acetate 3:19)

Sources & evidence

ORD record
ord-cc778a0fa05c42a5a5b15e3081212fba
Source dataset
uspto-grants-1993_07
Patent number
US05227393

Reaction notes

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