Potassium Carbonate → Phenyl 5-phenylisoxazol-3-ylcarbamate

HRID 631384

Reaktionsgleichung

Reaktionsgleichung von HRID 631384
[C:1]1([C:7]2[O:11][N:10]=[C:9]([NH2:12])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:13](=[O:16])([O-])[O-:14].[K+].[K+]>O1CCCC1>[C:1]1([C:7]2[O:11][N:10]=[C:9]([NH:12][C:13](=[O:16])[O:14][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

4

Edukt 2

HCID 11430Potassium CarbonateHCID 36207925-Phenyl-1,2-oxazol-3-amine

Produkt 1

HCID 59394374Phenyl 5-phenylisoxazol-3-ylcarbamateAusbeute 160,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

5-Phenylisoxazol-3-amine (428 mg, 2.67 mmol) in tetrahydrofuran (4.8 mL) was treated with potassium carbonate (481 mg, 3.47 mmol) and phenyl choloroformate (0.67 mL, 5.3 mmol). The reaction mixture was stirred at room temperature overnight. The mixture was filtered through a celite pad, washed with ethyl acetate and concentrated to dryness. The residue was taken into chloroform, washed with brine, and the organics dried (MgSO4) and concentrated. The residue was purified by silica gel chromatography (hexane/ethyl acetate 8:2) to give phenyl 5-phenylisoxazol-3-ylcarbamate (599 mg, 80%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 7.92 (bs, 1H), 7.78 (d, 2H), 7.45 (m, 6H), 7.26 (m, 2H), 7.12 (s, 1H); LC-MS (ESI) m/z 281 (M+H)+.

Aufarbeitung

  1. filtrationThe mixture was filtered through a celite pad
  2. washwashed with ethyl acetate
  3. concentrationconcentrated to dryness
  4. washwashed with brine
  5. dry with materialthe organics dried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate 8:2)

Quellen und Nachweise

ORD-Eintrag
ord-0b236e9b1cfa4e2e9753b78c47641366
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09320739B2

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