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

HRID 1609809Notes

Reaction equation

HRID 1609809 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

Conditions

Temperature
75 °C

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. customAfter removal of DMF in vacuo
  2. dissolutionthe residual solid was dissolved in CH2Cl2 (50 mL)
  3. washwashed with 1N Na2CO3 aq. solution
  4. dry with materialdried (MgSO4)
  5. customSeparation

Sources & evidence

ORD record
ord-e0c76ea6186d4352971ef7efa4ba6026
Source dataset
uspto-grants-2006_01
Patent number
US06982259B2

Reaction notes

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