Phosphorus oxychloride → HCID 18674967, compound

HRID 1634886Notes

Reaction equation

HRID 1634886 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([C:18]2[CH:23]=[CH:22][N+:21]([O-])=[CH:20][CH:19]=2)[CH:11]=[C:12]([O:16][CH3:17])[C:13]=1[O:14][CH3:15]>>[Cl:3][C:22]1[CH:23]=[C:18]([C:10]2[CH:9]=[C:8]([O:7][CH3:6])[C:13]([O:14][CH3:15])=[C:12]([O:16][CH3:17])[CH:11]=2)[CH:19]=[CH:20][N:21]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 186750144-(3,4,5-Trimethoxyphenyl)pyridine-N-oxide

Product 1

HCID 18674967HCID 18674967, compound

Conditions

Temperature
100 °C

Procedure

Phosphorus oxychloride (2 mL) was added to 4-(3,4,5-Trimethoxyphenyl)pyridine-N-oxide (27 mg) at 0° C., and the mixture was stirred at 100° C. for 5 hours. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate and neutralized with a saturated aqueous solution of sodium hydrogencarbonate at 0° C. The neutralized product was extracted with ethyl acetate, and the extract was washed with saturated brine and dried over anhydrous sodium sulfate. The residue was purified by column chromatography on silica gel (ethyl acetate) to obtain the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. customneutralized with a saturated aqueous solution of sodium hydrogencarbonate at 0° C
  4. extractionThe neutralized product was extracted with ethyl acetate
  5. washthe extract was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe residue was purified by column chromatography on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-62f8bfb40c614624866584b26b49cb17
Source dataset
uspto-grants-2003_01
Patent number
US06509329B1

Reaction notes

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