Imidazole → HCID 53799988, compound

HRID 581953Notes

Reaction equation

HRID 581953 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[NH:9]1[CH:13]=[CH:12][N:11]=[CH:10]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([N:9]2[CH:13]=[CH:12][N:11]=[CH:10]2)[N:3]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 169892,6-Dichloropyridine

Product 1

HCID 53799988HCID 53799988, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 2,6-dichloropyridine (5 g, 33.78 mmol), imidazole (2.3 g, 33.78 mmol) and potassium carbonate (4.66 g, 33.78 mmol) in DMF (50 ml) is heated to 85° C. over night. The cooled mixture is poured into ice-water and unreacted starting material is filtered off. The filtrate is acidified with diluted hydrochloric acid and is extracted once with ethyl acetate. The aqueous phase is rendered alkaline by addition of aqueous sodium hydroxide (10 M) and extracted with ethyl acetate. The organic extract is dried over sodium sulfate, concentrated under reduced pressure and eluted through silica gel with a mixture of ethyl acetate and methanol (9:1). Evaporation of solvent leaves 15a. Yield: 2.37 g (39%). Mp 71-73° C.

Workup

  1. filtrationis filtered off
  2. extractionis extracted once with ethyl acetate
  3. additionby addition of aqueous sodium hydroxide (10 M)
  4. extractionextracted with ethyl acetate
  5. extractionThe organic extract
  6. dry with materialis dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. washeluted through silica gel with a mixture of ethyl acetate and methanol (9:1)
  9. customEvaporation of solvent

Sources & evidence

ORD record
ord-811f07460ca2475286ff3cc1dd633e62
Source dataset
uspto-grants-1999_07
Patent number
US05922724

Reaction notes

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