4-Bromophenol → 3-(4-bromophenoxy)-6-(1H-imidazol-1-yl)pyridazine

HRID 466552Notes

Reaction equation

HRID 466552 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)=[CH:6][CH:7]=1.[Br:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>CC(=O)C>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:2]2[N:3]=[N:4][C:5]([N:8]3[CH:12]=[CH:11][N:10]=[CH:9]3)=[CH:6][CH:7]=2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 78084-BromophenolHCID 10340Sodium CarbonateHCID 27709033-Chloro-6-(1H-imidazol-1-yl)pyridazine

Product 1

HCID 151247883-(4-bromophenoxy)-6-(1H-imidazol-1-yl)pyridazine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4.5 parts of 3-chloro-6-(1H-imidazol-1-yl)pyridazine, 3.2 parts of 4-bromophenol, 4.2 parts of sodium carbonate and 80 parts of 2-propanone was stirred and refluxed over weekend. The reaction mixture was evaporated and the residue was taken up in water and 2,2'-oxybispropane. The layers were separated. The organic phase was dried, filtered and evaporated. The residue was crystallized from 2-propanol, yielding 3.5 parts of 3-(4-bromophenoxy)-6-(1H-imidazol-1-yl)pyridazine; mp. 168.4° C. (compound 6).

Workup

  1. temperaturerefluxed over weekend
  2. customThe reaction mixture was evaporated
  3. customThe layers were separated
  4. customThe organic phase was dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was crystallized from 2-propanol

Sources & evidence

ORD record
ord-be7365baf3b8402dba7023bf35b465df
Source dataset
uspto-grants-1992_10
Patent number
US05157035

Reaction notes

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