Acetonitrile → [1-(4-Cyanobenzyl)-1H-imidazol-5-yl]acetic acid methyl ester

HRID 342701

Reaction equation

HRID 342701 reaction equation
[CH3:1][O:2][C:3](=[O:29])[CH2:4][C:5]1N=[CH:7][N:8](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:9]=1.[C:30]([C:32]1[CH:39]=[CH:38][C:35]([CH2:36]Br)=[CH:34][CH:33]=1)#[N:31].C(#[N:42])C>>[CH3:1][O:2][C:3](=[O:29])[CH2:4][C:5]1[N:31]([CH2:30][C:32]2[CH:39]=[CH:38][C:35]([C:36]#[N:42])=[CH:34][CH:33]=2)[CH:7]=[N:8][CH:9]=1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 869964-(Bromomethyl)benzonitrileHCID 105239671-(triphenylmethyl)-1H-Imidazole-4-acetic acid methyl ester

Product 1

HCID 10634751[1-(4-Cyanobenzyl)-1H-imidazol-5-yl]acetic acid methyl ester

Conditions

Temperature
55 °C

Procedure

To a solution of the product from Step B (8.00 g, 20.9 mmol) in acetonitrile (70 mL) was added 4-cyanobenzyl bromide (4.10 g, 20.92 mmol) and heated at 55° C. for 3 hours. The reaction was cooled to room temperature and the resulting imidazolium salt was collected by filtration. The filtrate was heated at 55° C. for 18 hours. The reaction mixture was cooled to room temperature and evaporated in vacuo. To the residue was added EtOAc (70 mL) and the resulting precipitate collected by filtration. The precipitated imidazolium salts were combined, suspended in methanol (100 mL) and heated to reflux for 30 minutes. After this time, the solvent was removed in vacuo. The resulting residue was suspended in EtOAc (75 mL) and the solid isolated by filtration and washed with EtOAc. The solid was treated with sat. aq. NaHCO3 solution (300 mL) and CH2Cl2 (300 mL) and stirred at room temperature for 2 hours. The organic layer was separated, dried, (MgSO4) and evaporated in vacuo to afford the title compound as a white solid.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationthe resulting imidazolium salt was collected by filtration
  3. temperatureThe filtrate was heated at 55° C. for 18 hours
  4. temperatureThe reaction mixture was cooled to room temperature
  5. customevaporated in vacuo
  6. additionTo the residue was added EtOAc (70 mL)
  7. filtrationthe resulting precipitate collected by filtration
  8. temperatureheated
  9. temperatureto reflux for 30 minutes
  10. customAfter this time, the solvent was removed in vacuo
  11. customthe solid isolated by filtration
  12. washwashed with EtOAc
  13. additionThe solid was treated with sat. aq. NaHCO3 solution (300 mL) and CH2Cl2 (300 mL)
  14. customThe organic layer was separated
  15. customdried
  16. custom(MgSO4) and evaporated in vacuo

Sources & evidence

ORD record
ord-66a6c651181340e999bb461e5151c884
Source dataset
uspto-grants-1999_01
Patent number
US05859035

Linked notes

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