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

HRID 486446Notes

Reaction equation

HRID 486446 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].[Cl:8][C:9]1[N:10]=[N:11][C:12](Cl)=[CH:13][CH:14]=1>CN(C)C=O>[Cl:8][C:9]1[N:10]=[N:11][C:12]([N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 673313,6-Dichloropyridazine

Product 1

HCID 27709033-Chloro-6-(1H-imidazol-1-yl)pyridazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 47.6 parts of 1H-imidazole, 33.6 parts of sodium hydride dispersion 50% and 750 parts of N,N-dimethylformamide was stirred at room temperature for 15 minutes. The resulting solution was added to 106 parts of 3,6-dichloropyridazine in 750 parts of N,N-dimethylformamide and the whole was further stirred for 2 days at room temperature. The product was extracted with trichloromethane. The extract was dried, filtered and evaporated. The residue was crystallized from methanol. The product was filtered off, washed with petroleumether and dried, yielding 48.5 parts of 3-chloro-6-(1H-imidazol-1-yl)pyridazine: mp. 182.9° C. (compound 1).

Workup

  1. stirringthe whole was further stirred for 2 days at room temperature
  2. extractionThe product was extracted with trichloromethane
  3. customThe extract was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was crystallized from methanol
  7. filtrationThe product was filtered off
  8. washwashed with petroleumether
  9. customdried

Sources & evidence

ORD record
ord-de5f7f067c5e426cb33cd93ba752ddfc
Source dataset
uspto-grants-1994_03
Patent number
US05292738

Reaction notes

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