Imidazole → 3-Chloro-6-(1H-imidazol-1-yl)pyridazine

HRID 1270455Notes

Reaction equation

HRID 1270455 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[Cl:6][C:7]1[N:8]=[N:9][C:10](Cl)=[CH:11][CH:12]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:6][C:7]1[N:8]=[N:9][C:10]([N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 673313,6-Dichloropyridazine

Product 1

HCID 27709033-Chloro-6-(1H-imidazol-1-yl)pyridazineYield 83.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of imidazole (0.613 g, 8 mmol) and 3,6-dichloropyridazine (1.55 g, 10 mmol), K2CO3 (4.15 g) and DMF (15 mL) was heated at 70–80° C. overnight. After removal of DMF in vacuo, the residual solid was dissolved in CH2Cl2 (50 mL), washed with 1N Na2CO3 aq. solution, and dried (MgSO4). Separation using column chromatography (CH2Cl2/methanol 100:1) afforded 3-chloro-6-(imidazol-1-yl)pyridazine (1.2 g) as a white solid.

Workup

  1. temperaturewas heated at 70–80° C. overnight
  2. customAfter removal of DMF in vacuo
  3. dissolutionthe residual solid was dissolved in CH2Cl2 (50 mL)
  4. washwashed with 1N Na2CO3 aq. solution
  5. dry with materialdried (MgSO4)
  6. customSeparation

Sources & evidence

ORD record
ord-73bfa0823ce540c7a2ff9893e3bd240f
Source dataset
uspto-grants-2007_04
Patent number
US07202263B2

Reaction notes

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