Imidazole → 4-(1-Imidazolylmethyl)benzonitrile

HRID 2108017Notes

Reaction equation

HRID 2108017 reaction equation
C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[NH:9]1[CH:13]=[CH:12][N:11]=[CH:10]1.Cl[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[CH:18][CH:17]=1>CCOCC.CC(C)=O>[NH:9]1[CH:13]=[CH:12][N:11]=[C:10]1[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 701274-(Chloromethyl)benzonitrile

Product 1

HCID 111481024-(1-Imidazolylmethyl)benzonitrile

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

To 48.0 L of acetone under nitrogen is added 4.326 Kg of potassium carbonate, 0.26 Kg of potassium iodide, 3.2 Kg of imidazole and 4.745 Kg of alpha-chloro-4-tolunitrile. The mixture is stirred at 45° under nitrogen for 26 hours. The reaction is cooled, filtered and the solvent is evaporated at reduced pressure. The residue is redissolved in 40 L of methylene chloride, washed with 40 L of water and twice with 10 L of water. The organic phase is dried over magnesium sulfate and evaporated to yield the crude product which is stirred with 6.4 L of ether for 2 hours. The solid is filtered, washed with 9 L of ether and dried at 40° and 20 mm Hg for 17 hours to yield 4-(1-imidazolylmethyl)-benzonitrile, the compound of Example 1.

Workup

  1. temperatureThe reaction is cooled
  2. filtrationfiltered
  3. customthe solvent is evaporated at reduced pressure
  4. dissolutionThe residue is redissolved in 40 L of methylene chloride
  5. washwashed with 40 L of water and twice with 10 L of water
  6. dry with materialThe organic phase is dried over magnesium sulfate
  7. customevaporated
  8. customto yield the crude product which
  9. filtrationThe solid is filtered
  10. washwashed with 9 L of ether
  11. customdried at 40°

Sources & evidence

ORD record
ord-9808b8c93f75431fb76cbe6153e71291
Source dataset
uspto-grants-1990_06
Patent number
US04937250

Reaction notes

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