Phosphorus oxychloride → HCID 19436779, compound

HRID 1735016Notes

Reaction equation

HRID 1735016 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:9][C:10]2[N:14]([CH3:15])[N:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[N:6]=[N:7][CH:8]=1.P(Cl)(Cl)([Cl:22])=O>C(Cl)(Cl)(Cl)Cl>[Cl:22][C:8]1[N:7]=[N:6][C:5]([O:9][C:10]2[N:14]([CH3:15])[N:13]=[C:12]([C:16]([F:19])([F:17])[F:18])[CH:11]=2)=[CH:4][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 19436789HCID 19436789, compound

Product 1

HCID 19436779HCID 19436779, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

5-Methoxy-3-[[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy]pyridazine, 1-oxide (Compound No. 55, 1.0 g, 0.00344 mole) and phosphorus oxychloride (0.6 g, 0.00391 mole) were refluxed under N2 in carbon tetrachloride (40 mL) for 18 hours. The mixture was then partitioned between water and ethyl acetate. The aqueous layer was extracted again with ethyl acetate and the combined organic layers were washed with saturated sodium bicarbonate, brine, filtered through silica gel with ethyl acetate and evaporated in vacuo. The crude solid was recrystallized from ethyl acetate/cyclohexane to give 3-chloro-4-methoxy-6-[[1-methyl-3-(trifluoromethyl)- 1H-pyrazol-5-yl]oxy]pyridazine (0.681 g, 64% yield) as an off-white solid.

Workup

  1. customThe mixture was then partitioned between water and ethyl acetate
  2. extractionThe aqueous layer was extracted again with ethyl acetate
  3. washthe combined organic layers were washed with saturated sodium bicarbonate, brine
  4. filtrationfiltered through silica gel with ethyl acetate
  5. customevaporated in vacuo
  6. customThe crude solid was recrystallized from ethyl acetate/cyclohexane

Sources & evidence

ORD record
ord-53f8a81ecffd4723abb105ed88638569
Source dataset
uspto-grants-1996_07
Patent number
US05536701

Reaction notes

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