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

HRID 1585903Notes

Reaction equation

HRID 1585903 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-0a5f31d60b2a48a69cf2052e1752506b
Source dataset
uspto-grants-1999_08
Patent number
US05939439

Reaction notes

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