Imidazole → 2-Hydroxy-4-imidazol-1-ylmethyl-benzonitrile

HRID 1421725Notes

Reaction equation

HRID 1421725 reaction equation
Br[CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[C:5]([OH:11])[CH:4]=1.[NH:12]1[CH:16]=[CH:15][N:14]=[CH:13]1>CN(C=O)C>[OH:11][C:5]1[CH:4]=[C:3]([CH2:2][N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)[CH:10]=[CH:9][C:6]=1[C:7]#[N:8]

Participants

4

Reactant 2

HCID 795ImidazoleHCID 216969934-(Bromomethyl)-2-hydroxybenzonitrile

Product 1

HCID 216970282-Hydroxy-4-imidazol-1-ylmethyl-benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Bromomethyl-2-hydroxybenzonitrile (0.222 g, 1.045 mmol) and imidazole (0.356 g, 5.23 mmol) were stirred in DMF (10 mL) at ambient temperature for 18 hr. The reaction mixture was concentrated in vacuo to remove the DMF, and the residue was chromatographed (SiO2, 2-5% CH3OH in CH2Cl2) to give the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto remove the DMF
  3. customthe residue was chromatographed (SiO2, 2-5% CH3OH in CH2Cl2)

Sources & evidence

ORD record
ord-570b20861e5e454a9d7a4d8f0351e9aa
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

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