Acetic Anhydride → ethyl 2-(5-acetamido-3-phenyl-1H-pyrazol-1-yl)acetate

HRID 1615727Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1615727
[NH2:1][C:2]1[N:6]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:3]=1.[C:19](OC(=O)C)(=[O:21])[CH3:20]>N1C=CC=CC=1>[C:19]([NH:1][C:2]1[N:6]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:3]=1)(=[O:21])[CH3:20]

Komponenten

4

Edukt 2

HCID 7918Acetic AnhydrideHCID 820314ethyl 2-(5-amino-3-phenyl-1H-pyrazol-1-yl)acetate

Produkt 1

HCID 86717316ethyl 2-(5-acetamido-3-phenyl-1H-pyrazol-1-yl)acetateAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a solution of ethyl 2-(5-amino-3-phenyl-pyrazol-1-yl)acetate (49 g, 0.17 mol) in pyridine (200 mL) was added acetic anhydride (17.4 g, 0.17 mol) dropwise at 0° C. under an atmosphere of nitrogen. The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was concentrated in vacuo. The residue was diluted with CH2Cl2 and water. The layers were separated and the organic layer was washed with water and brine, dried (MgSO4) and concentrated in vacuo. CH2Cl2 was added to the residue and the solid was collected by filtration, yielding the title compound as a solid (22 g). The mother liquors were concentrated in vacuo and washed with cold CH2Cl2 to yield a second batch of 15 g.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionThe residue was diluted with CH2Cl2 and water
  3. customThe layers were separated
  4. washthe organic layer was washed with water and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. additionCH2Cl2 was added to the residue
  8. filtrationthe solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-34952eff153f4ec59fc53a7d6ca767d7
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765762B2

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