3,5-Dimethylphenol → 3-(3,5-dimethylphenoxy)-6-(1H-imidazol-1-yl)pyridazine

HRID 466551Notes

Reaction equation

HRID 466551 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[H-].[Na+].Cl[C:13]1[N:14]=[N:15][C:16]([N:19]2[CH:23]=[CH:22][N:21]=[CH:20]2)=[CH:17][CH:18]=1>CN(C)C=O>[CH3:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([CH3:8])[CH:7]=1)[O:9][C:13]1[N:14]=[N:15][C:16]([N:19]2[CH:23]=[CH:22][N:21]=[CH:20]2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 79483,5-DimethylphenolHCID 24758Sodium hydrideHCID 27709033-Chloro-6-(1H-imidazol-1-yl)pyridazine

Product 1

HCID 151247843-(3,5-dimethylphenoxy)-6-(1H-imidazol-1-yl)pyridazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 3 parts of 3,5-dimethylphenol, 1.25 parts of sodium hydride dispersion 50% and 25 parts of N,N-dimethylformamide was stirred for 15 minutes. Then there was added a solution of 4.5 parts of 3-chloro-6-(1H-imidazol-1-yl)pyridazine in 25 parts of N,N-dimethylformamide and the whole was stirred over weekend at 50° C. The reaction mixture was poured onto water and the product was extracted with trichloromethane. The extract was dried, filtered and evaporated. The residue was crystallized from 2-propanone, yielding 3.5 parts of 3-(3,5-dimethylphenoxy)-6-(1H-imidazol-1-yl)pyridazine; mp. 169.8° C. (compound 2).

Workup

  1. stirringthe whole was stirred over weekend at 50° C
  2. additionThe reaction mixture was poured onto water
  3. extractionthe product was extracted with trichloromethane
  4. customThe extract was dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was crystallized from 2-propanone

Sources & evidence

ORD record
ord-4169f1d34ecf4379bb649a1803e2c4a6
Source dataset
uspto-grants-1992_10
Patent number
US05157035

Reaction notes

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