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

HRID 379025Notes

Reaction equation

HRID 379025 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-hydroxy-benzonitrile (0.22 g, 1.05 mmol) and imidazole (0.36 g, 5.23 mmol) were dissolved in DMF (10 mL) with stirring at ambient temperature. After stirring for 18 h the reaction mixture was concentrated in vacuo and purified by silica gel chromatography eluting with 2% CH3OH/CH2Cl2 to 5% CH3OH/CH2Cl2 to give the title compound.

Workup

  1. stirringAfter stirring for 18 h the reaction mixture
  2. concentrationwas concentrated in vacuo
  3. custompurified by silica gel chromatography
  4. washeluting with 2% CH3OH/CH2Cl2 to 5% CH3OH/CH2Cl2

Sources & evidence

ORD record
ord-fd218a04b3084973923057e2d5ebd771
Source dataset
uspto-grants-2001_10
Patent number
US06297239B1

Reaction notes

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