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

HRID 588619Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 588619
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][C:9]1[N:13]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:12]=[C:11]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:10]=1>N1C=CC=CC=1>[C:1]([NH:8][C:9]1[N:13]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:12]=[C:11]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:10]=1)(=[O:3])[CH3:2]

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 94,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Acetic anhydride (12.7 mL, 134.8 mmol) was added dropwise to a solution of ethyl 2-(5-amino-3-phenyl-pyrazol-1-yl)acetate (31.5 g, 128.4 mmol) in pyridine (200 mL) at 0° C. under an atmosphere of nitrogen. Upon complete addition, the reaction mixture was warmed to room temperature and stirred for 16 h. The reaction mixture was concentrated in vacuo. The residue was diluted in CH2Cl2 (250 mL). The organic phase was washed with water and brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was triturated from diethyl ether, filtered and dried to provide the title compound as a white solid (34.81 g).

Aufarbeitung

  1. additionUpon complete addition
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additionThe residue was diluted in CH2Cl2 (250 mL)
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was triturated from diethyl ether
  9. filtrationfiltered
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-c3844116f61d43339374b4532ab079d4
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09227976B2

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