Phosphorus oxychloride → HCID 59641681, compound

HRID 2266302Notes

Reaction equation

HRID 2266302 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[CH:12]=[C:11]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[C:10](O)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:25])=O>>[CH2:1]([N:8]1[C:13](=[O:14])[CH:12]=[C:11]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[C:10]([Cl:25])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178515600HCID 178515600, compound

Product 1

HCID 59641681HCID 59641681, compoundYield 69%

Conditions

Temperature
95 °C

Procedure

A suspension of 2-benzyl-5-(4-chlorophenyl)-6-hydroxypyridazin-3(2H)-one (8.5 g, 27.2 mmol) in phosphorus oxychloride (50 mL) was stirred at 95° C. for 1 h. Analysis by HPLC/MS indicated the starting material had been consumed. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The obtained residue was diluted with EtOAc. The resulting EtOAc solution was washed with saturated aqueous NaHCO3, saturated aqueous NaCl, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude product was purified using a silica gel cartridge (330 g) eluting with a gradient of EtOAc (0-40%) in hexanes to afford 6.2 g (69%) of the title compound as a white solid. HPLC/MS (method A): retention time=3.80 min, (M+H)+=331.0. 1H NMR (CDCl3, 400 MHz): δ 7.27-7.80 (m, 9H), 6.88 (s, 1H), 5.36 (s, 2H).

Workup

  1. customhad been consumed
  2. temperatureAfter cooling to room temperature
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. additionThe obtained residue was diluted with EtOAc
  5. washThe resulting EtOAc solution was washed with saturated aqueous NaHCO3, saturated aqueous NaCl
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was purified
  10. washeluting with a gradient of EtOAc (0-40%) in hexanes

Sources & evidence

ORD record
ord-a5caaeb55c6b4f0e84f9ebf124a0a99e
Source dataset
uspto-grants-2010_12
Patent number
US07858639B2

Reaction notes

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