Phosphorus oxychloride → HCID 86231906, compound

HRID 499158Notes

Reaction equation

HRID 499158 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[N:15]=[N:14][C:13](O)=[CH:12][CH:11]=1.P(Cl)(Cl)([Cl:19])=O>C(Cl)CCl>[Cl:19][C:13]1[N:14]=[N:15][C:10]([C:2]2[NH:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:1]=2)=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178515895HCID 178515895, compound

Product 1

HCID 86231906HCID 86231906, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

6-(1H-Benzoimidazol-2-yl)pyridazin-3-ol (0.322 g, 1.570 mmol) was suspended in ethylene dichloride (10 mL). Phosphorus oxychloride was added (15 mL) and the mixture was stirred at reflux for 48 hours. All solvents were removed and the residue was washed with saturated NaHCO3 and extracted with ethyl acetate. The organic solution was dried, concentrated and purified by column chromatography to yield 0.075 g of 2-(6-chloro-pyridazin-3-yl)-1H-benzoimidazole (0.32 mmol, 20% yield).

Workup

  1. temperatureat reflux for 48 hours
  2. customAll solvents were removed
  3. washthe residue was washed with saturated NaHCO3
  4. extractionextracted with ethyl acetate
  5. customThe organic solution was dried
  6. concentrationconcentrated
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-aeedda2b32684bf5b36e4de656e3f1aa
Source dataset
uspto-grants-2010_08
Patent number
US07767677B2

Reaction notes

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