Phosphorus oxychloride → HCID 86682371, compound

HRID 2283656Notes

Reaction equation

HRID 2283656 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:4]=1[C:13]1[C:18]([CH3:19])=[N:17][NH:16][C:15](=O)[CH:14]=1.C(=O)(O)[O-].[Na+].P(Cl)(Cl)([Cl:28])=O>>[Cl:28][C:15]1[N:16]=[N:17][C:18]([CH3:19])=[C:13]([C:4]2[CH:5]=[C:6]([C:9]([F:12])([F:11])[F:10])[CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[CH:14]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 68047231HCID 68047231, compound

Product 1

HCID 86682371HCID 86682371, compound

Conditions

Temperature
0 °C

Procedure

5-[2-Methoxy-5-(trifluoromethyl)phenyl]-6-methylpyridazin-3(2H)-one (Preparation 41, 1.1 g, 39 mmol) and phosphorus oxychloride (20 mL) were heated to 100° C. for 3 hours. The reaction mixture was then cooled to 0° C. and poured onto ice before being neutralised with sodium bicarbonate. The mixture was extracted with dichloromethane (3×100 mL) and the combined organic layer washed with water (50 mL) then saturated aqueous sodium chloride solution (50 mL). The organics were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by silica gel column chromatography (20% ethyl acetate in heptane elution) to afford the title compound as an off-white solid (900 mg).

Workup

  1. additionpoured onto ice
  2. extractionThe mixture was extracted with dichloromethane (3×100 mL)
  3. washthe combined organic layer washed with water (50 mL)
  4. dry with materialThe organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by silica gel column chromatography (20% ethyl acetate in heptane elution)

Sources & evidence

ORD record
ord-cb8b1acba1da418ea7f073d75fabba5d
Source dataset
uspto-grants-2015_09
Patent number
US09145407B2

Reaction notes

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