Imidazole → 4-(1-Imidazolylmethyl)benzonitrile

HRID 1111160Notes

Reaction equation

HRID 1111160 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[N:10])=[CH:5][CH:4]=1.[NH:11]1[CH:15]=[CH:14][N:13]=[CH:12]1>ClCCl.O>[NH:11]1[CH:15]=[CH:14][N:13]=[C:12]1[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[N:10])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 795ImidazoleHCID 869964-(Bromomethyl)benzonitrile

Product 1

HCID 111481024-(1-Imidazolylmethyl)benzonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of alpha-bromo-4-tolunitrile (86.6 g) in dichloromethane (1000 mL) is mixed with imidazole (68.0 g). The mixture is stirred at ambient temperature for 15 hours and then diluted with water (1000 mL). Any undissolved solid is removed by filtration and the separated organic solution is then repeatedly washed with water (5×200 mL) to remove excess imidazole, and then dried (MgSO4). The crude product obtained upon evaporation of the solvent can be purified by trituration with cold diethyl ether (200 mL) to obtain 4-(1-imidazolylmethyl)-benzonitrile, m.p. 99°-101°; HCl salt, m.p. 142°-144°.

Workup

  1. customAny undissolved solid is removed by filtration
  2. washthe separated organic solution is then repeatedly washed with water (5×200 mL)
  3. customto remove excess imidazole
  4. dry with materialdried (MgSO4)
  5. customThe crude product obtained upon evaporation of the solvent
  6. customcan be purified by trituration with cold diethyl ether (200 mL)

Sources & evidence

ORD record
ord-fc63bdcd4ab94ddabc8391971bb77600
Source dataset
uspto-grants-1990_12
Patent number
US04978672

Reaction notes

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