Phosphorus oxychloride → HCID 58046417, compound

HRID 2046387Notes

Reaction equation

HRID 2046387 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[N:12][NH:11][C:10](=O)[CH:9]=2)=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:17]>>[Cl:17][C:10]1[N:11]=[N:12][CH:13]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH:9]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 67122910HCID 67122910, compound

Product 1

HCID 58046417HCID 58046417, compound

Conditions

Temperature
110 °C

Procedure

5-(4-Fluorophenyl)pyridazin-3(2H)-one (2.15 g, 11.3 mmol) was dissolved in POCl3 (133 ml) and the mixture was refluxed at 110° C. for 30 min. The reaction was cooled in an ice bath and slowly quenched with aqueous sodium hydrogen carbonate (200 mL). The mixture was extracted with ethyl acetate (3×200 mL). The combined organics were washed with water and brine, dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure to afford the title compound. 1H NMR (500 MHz, CD3SOCD3) δ 9.67 (d, 1H); 8.28 (d, 1H); 8.07 (dd, 2H); 7.42 (t, 2H).

Workup

  1. temperatureThe reaction was cooled in an ice bath
  2. customslowly quenched with aqueous sodium hydrogen carbonate (200 mL)
  3. extractionThe mixture was extracted with ethyl acetate (3×200 mL)
  4. washThe combined organics were washed with water and brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8daf62f8d478467ebe338f7601c3417d
Source dataset
uspto-grants-2013_11
Patent number
US08592425B2

Reaction notes

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