Triethylamine → HCID 10727133, compound

HRID 1195801Notes

Reaction equation

HRID 1195801 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[NH:15][O:16][C:17](=O)[CH:18]=2)=[CH:10][CH:9]=1.C(N(CC)CC)C>>[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:18]=[C:17]([Cl:3])[O:16][N:15]=2)=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 24215067HCID 24215067, compound

Product 1

HCID 10727133HCID 10727133, compound

Procedure

To 30 g of phosphorus oxychloride were added 7.4 g (39 mmol) of 3-(4-methoxyphenyl)isoxazol-5-one, followed by the dropwise addition of 4 g (40 mmol) of triethylamine. After completion of the dropwise addition, the reaction mixture was stirred at 120°-125° C. for 4 hours. The solvent was then distilled off under reduced pressure. Ice water (100 ml) was added to the residue, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water and then dried. Purification by silica gel column chromatography (solvent: hexane/ethyl acetate=10/1) gave the title compound as colorless crystals.

Workup

  1. additionAfter completion of the dropwise addition
  2. distillationThe solvent was then distilled off under reduced pressure
  3. additionIce water (100 ml) was added to the residue
  4. extractionthe resulting mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. customdried
  7. customPurification by silica gel column chromatography (solvent: hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-dc6addb902c7470a84aad05d877c13e2
Source dataset
uspto-grants-1992_05
Patent number
US05112841

Reaction notes

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