2-Methylbenzoic acid → HCID 16722533, Verbindung

HRID 1983082Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1983082
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]([NH:15][NH2:16])=[O:14].P(Cl)(Cl)(Cl)=O.[C:22]1([CH3:31])[C:23]([C:28](O)=O)=[CH:24][CH:25]=[CH:26][CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]1[O:14][C:31]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH3:28])=[N:16][N:15]=1

Komponenten

6

Edukt 4

HCID 83732-Methylbenzoic acidHCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 7279245-Methyl-3-phenyl-4-isoxazolecarbohydrazide

Produkt 1

HCID 16722533HCID 16722533, VerbindungAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a suspension of 5-methyl-3-phenyl-isoxazole-4-carboxylic acid hydrazide (200 mg, 0.92 mmol) in phosphorus oxychloride (1.68 mL, 18.4 mmol) was added o-toluic acid (188 mg, 1.38 mmol) and was stirred for 30 min at ambient temperature. The suspension was heated for 2 h at 90° C. whereupon it became homogeneous. After cooling to ambient temperature it was then poured onto a mixture of ethyl acetate (20 mL) and aqueous sodium carbonate (saturated, 20 mL). The aqueous phase was then separated and extracted with ethyl acetate (20 mL). The combined organic extracts were then washed with aqueous sodium carbonate and brine. Concentration and trituration in tert-butylmethylether (3 mL) afforded the title compound (99 mg, 34%) as a white solid. MS: m/e=318.1 [M+H]+.

Aufarbeitung

  1. temperatureThe suspension was heated for 2 h at 90° C. whereupon it
  2. temperatureAfter cooling to ambient temperature it
  3. customThe aqueous phase was then separated
  4. extractionextracted with ethyl acetate (20 mL)
  5. washThe combined organic extracts were then washed with aqueous sodium carbonate and brine
  6. concentrationConcentration and trituration in tert-butylmethylether (3 mL)

Quellen und Nachweise

ORD-Eintrag
ord-f3d9dca0b88740958ba5af5e83fb257b
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07541372B2

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