Imidazole → HCID 21942691, compound

HRID 431868Notes

Reaction equation

HRID 431868 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([I:13])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].C(=O)([O-])[O-].[K+].[K+].[NH:20]1[CH:24]=[CH:23][N:22]=[CH:21]1>CN(C)C=O.O>[N:20]1([CH2:2][C:3]2[CH:4]=[C:5]([CH:10]=[C:11]([I:13])[CH:12]=2)[C:6]([O:8][CH3:9])=[O:7])[CH:24]=[CH:23][N:22]=[CH:21]1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 21942682HCID 21942682, compound

Product 1

HCID 21942691HCID 21942691, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of methyl 3-(bromomethyl)-5-iodobenzoate (500 mg, 1.4 mmol), potassium carbonate (388 mg, 2.8 mmol), and imidazole (96 mg, 1.4 mmol) in N,N-dimethylformamide (4 mL) was heated at 70° C. for 3 hours. After cooling, the reaction mixture was diluted with water and then extracted with dichloromethane. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated. Silica gel chromatography using 100% ethyl acetate afforded 242 mg (51%) of methyl 3-(imidazol-1-ylmethyl)-5-iodobenzoate as a white solid.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ea434db4238240858fad05fc0784659c
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Reaction notes

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