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

HRID 379031Notes

Reaction equation

HRID 379031 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/CH2C12 to 5% CH3OH/CH2Cl2 to give the title compound.

Workup

  1. stirringAfter stirring for 18 h
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. custompurified by silica gel chromatography
  4. washeluting with 2% CH3OH/CH2C12 to 5% CH3OH/CH2Cl2

Sources & evidence

ORD record
ord-b0d36694988949c584188e150db9557d
Source dataset
uspto-grants-2001_10
Patent number
US06297239B1

Reaction notes

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