Phosphorus oxychloride → HCID 59641678, compound

HRID 2250345Notes

Reaction equation

HRID 2250345 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[CH:10][C:11](=O)[NH:12][N:13]=1.P(Cl)(Cl)([Cl:24])=O>>[Cl:24][C:11]1[N:12]=[N:13][C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])=[C:9]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[CH:10]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 59641676HCID 59641676, compound

Product 1

HCID 59641678HCID 59641678, compoundYield 97%

Conditions

Temperature
95 °C

Procedure

A suspension of 6-(2-chlorophenyl)-5-(4-chlorophenyl)pyridazin-3(2H)-one (4.1 g, 12.9 mmol) in phosphorus oxychloride (15 mL) was stirred at 95° C. for 1 h. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was partitioned between EtOAc and saturated aqueous NaHCO3. The separated aqueous layer was extracted with EtOAc (40 mL×2). The combined organic was washed with saturated aqueous NaHCO3, saturated aqueous NaCl, dried (Na2SO4) and concentrated under reduced pressure to afford 4.2 g (97%) of the title compound as a pink foam. LC/MS (method A): retention time=3.50 min, (M+H)+=335.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customThe residue was partitioned between EtOAc and saturated aqueous NaHCO3
  4. extractionThe separated aqueous layer was extracted with EtOAc (40 mL×2)
  5. washThe combined organic was washed with saturated aqueous NaHCO3, saturated aqueous NaCl
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1216c996ff8e42ddafe41d20a13bdc7d
Source dataset
uspto-grants-2008_01
Patent number
US07317012B2

Reaction notes

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