4-Chlorophenol → HCID 54094554, compound

HRID 1075545Notes

Reaction equation

HRID 1075545 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH:12]([C:14]1[C:15]2[N:16]([C:20]([CH3:23])=[N:21][N:22]=2)[N:17]=[CH:18][CH:19]=1)[CH3:13]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:12]([C:14]2[C:15]3[N:16]([C:20]([CH3:23])=[N:21][N:22]=3)[N:17]=[CH:18][CH:19]=2)[CH3:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 46844-ChlorophenolHCID 24758Sodium hydrideHCID 53653159HCID 53653159, compound

Product 1

HCID 54094554HCID 54094554, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

p-Chlorophenol (0.25 g) was added to a suspension of sodium hydride (0.08 g) in anhydrous dimethylformamide (5 ml). The resultant mixture was stirred at room temperature for 30 minutes then 8-(1-bromoethyl)-3-methyl-1,2,4-triazolo[4,3-b]pyridazine (0.38 g), in dimethylformamide (20 ml), was added dropwise and the mixture stirred for 1 hour. The reaction mixture was concentrated to dryness and the residue dissolved in dichloromethane (50 ml). The solution was washed with 5% aqueous sodium hydroxide and then with water. The organic layer was separated and dried with sodium sulphate, filtered and concentrated to dryness. The white solid obtained was recrystallized from ethyl acetate:hexane to give 8-[1-(4-chlorophenoxy)ethyl]-3-methyl-1,2,4-triazolo[4,3-b]pyridazine. m.p. 158-160° C.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. dissolutionthe residue dissolved in dichloromethane (50 ml)
  3. washThe solution was washed with 5% aqueous sodium hydroxide
  4. customThe organic layer was separated
  5. dry with materialdried with sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe white solid obtained
  9. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-496389e7d15e48238ba568eba6ba0763
Source dataset
uspto-grants-1999_05
Patent number
US05905079

Reaction notes

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