Imidazole → 265107-80-0

HRID 2362252Notes

Reaction equation

HRID 2362252 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[NH:11]1[CH:15]=[CH:14][N:13]=[CH:12]1>>[N:11]1([C:2]2[N:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=2)[CH:15]=[CH:14][N:13]=[CH:12]1

Participants

3

Reactant 2

HCID 795ImidazoleHCID 27796981-(6-Chloropyridin-3-yl)ethan-1-one

Product 1

HCID 58305612265107-80-0Yield 67%

Conditions

Temperature
125 °C

Procedure

To a 25 mL vial which contained 1-(6-chloro-pyridin-3-yl)-ethanone (1.5 g, 10 mmol.) was added 1H-imidazole (3 g, 50 mmol.) at rt. The mixture was stirred at 120-130° C. for 2 h and cooled to rt. The contents were poured into 150 mL ice-water solution and extracted with EtOAc (3×100 mL). The combined organic layers was washed with water (3×50 mL), brine (50 mL) and dried over Na2SO4. The solvent was removed under vacuum to yield the crude which was purified by column to afford desired 1-(6-imidazol-1-yl-pyridin-3-yl)-ethanone (1.25 g, 67%).

Workup

  1. temperaturecooled to rt
  2. extractionextracted with EtOAc (3×100 mL)
  3. washThe combined organic layers was washed with water (3×50 mL), brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed under vacuum
  6. customto yield the crude which
  7. customwas purified by column

Sources & evidence

ORD record
ord-0ca01014e9cc4eddab5fe6b18f86f27b
Source dataset
uspto-grants-2014_04
Patent number
US08691816B2

Reaction notes

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