Phosphorus oxychloride → HCID 57793931, compound

HRID 1678388Notes

Reaction equation

HRID 1678388 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([CH3:14])=[N:12][NH:11][C:10](=O)[C:9]=2[C:16]2[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=2[F:23])=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:26])=O>>[Cl:26][C:10]1[N:11]=[N:12][C:13]([CH3:14])=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:9]=1[C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[F:23]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 57793940HCID 57793940, compound

Product 1

HCID 57793931HCID 57793931, compoundYield 95.7%

Conditions

Temperature
110 °C

Procedure

2.86 g of 5-(4-chlorophenyl)-4-(2,5-difluorophenyl)-6-methyl-2H-pyridazin-3-one and 6.5 g of phosphorus oxychloride were mixed and stirred at 110° C. for 1 hour. The reaction mixture was allowed to cool down to room temperature and concentrated under reduced pressure. To the residue was added ethyl acetate and ice water, and was separated to two layer. The organic layer was washed sequentially with water and saturated brine, and dried over anhydrous sodium sulfate, then, concentrated. The residue was subjected to silica gel column chromatography (elution solvent; hexane:ethyl acetate=3:1, to obtain 2.89 g of 3-chloro-5-(4-chlorophenyl)-4-(2,5-difluorophenyl)-6-methyl pyridazine (hereinafter, referred to as compound (xiii) of the present invention).

Workup

  1. temperatureto cool down to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionTo the residue was added ethyl acetate and ice water
  4. customwas separated to two layer
  5. washThe organic layer was washed sequentially with water and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. washelution solvent

Sources & evidence

ORD record
ord-cfa031632da7443a8e3b34d3d2425044
Source dataset
uspto-grants-2011_08
Patent number
US08008512B2

Reaction notes

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