3,4-Dichlorophenol → HCID 22047707, compound

HRID 1179681Notes

Reaction equation

HRID 1179681 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1.[Cl:9][C:10]1[CH:11]=[C:12]([OH:17])[CH:13]=[CH:14][C:15]=1[Cl:16].[OH-].[K+].CCCCCCC>CS(C)=O>[Cl:8][C:5]1[N:4]=[N:3][C:2]([O:17][C:12]2[CH:13]=[CH:14][C:15]([Cl:16])=[C:10]([Cl:9])[CH:11]=2)=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 72583,4-DichlorophenolHCID 8900HeptaneHCID 14797Potassium HydroxideHCID 673313,6-Dichloropyridazine

Product 1

HCID 22047707HCID 22047707, compoundYield 21.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 3,6-dichloropyridazine (4.47 g, 30.0 mmol), 3,4-dichlorophenol (4.89 g, 30.0 mmol) and potassium hydroxide (1.68 g, 30.0 mmol) in dimethyl sulfoxide (20 mL) was heated at 60° C. overnight. The solvent was removed by evaporation in vacuo. The residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane 50:50). Small amounts of starting material were removed by kugelrohr distillation. Crystallisation from ethyl acetate:heptane yielded the title compound (1.74 g, 21% yield) as a white solid.

Workup

  1. customThe solvent was removed by evaporation in vacuo
  2. customThe residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane 50:50)
  3. customSmall amounts of starting material were removed by kugelrohr distillation
  4. customCrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-511578cdfbf242838d483affe9b7852e
Source dataset
uspto-grants-2007_10
Patent number
US07279470B2

Reaction notes

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