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5-amino-3H-pyrazol-3-one → 7-(2,3-Dichlorophenyl)-1,2,4,7-tetrahydro-5-methyl-2-oxopyrazolo[1,5-a]pyrimidine-6-carboxylic acid, ethyl ester

HRID 1252989
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1252989
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]=[C:10]([C:16](=O)[CH3:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12].[NH2:19][C:20]1[N:21]=[N:22][C:23](=[O:25])[CH:24]=1>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[N:21]2[NH:22][C:23](=[O:25])[CH:24]=[C:20]2[NH:19][C:16]([CH3:17])=[C:10]1[C:11]([O:13][CH2:14][CH3:15])=[O:12]
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Komponenten

5

Edukt 2

HCID 42555565-amino-3H-pyrazol-3-oneHCID 54112468Ethyl 2-[(2,3-dichlorophenyl)methylidene]-3-oxobutanoate

Produkt 1

HCID 141304317-(2,3-Dichlorophenyl)-1,2,4,7-tetrahydro-5-methyl-2-oxopyrazolo[1,5-a]pyrimidine-6-carboxylic acid, ethyl esterAusbeute 38,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel
HCID 8857
Ethyl Acetate
Lösungsmittel

Versuchsvorschrift

A solution of 2-[(2,3-dichlorophenyl)methylene]-3-oxobutanoic acid, ethyl ester (2.8 g; 10.0 mmole) in dimethylformamide (7 ml) was treated with 3-amino-5-pyrazolone (990 mg) and the resulting mixture was heated at 65° C.±5° for 15 hours. The reaction mixture was allowed to cool to room temperature and then diluted with ethyl acetate. The solution was washed with water, brine, and dried over anhydrous magnesium sulfate. Evaporation of the solvent provided a foam which was purified by flash chromatography (7% methanol in dichloromethane). The product was crystallized from acetonitrile-isopropyl ether to provide the title compound as a solid (1.42 g; melting point 213°-218° C.; sinters above 155° C.).

Aufarbeitung

  1. temperaturethe resulting mixture was heated at 65° C.±5° for 15 hours
  2. washThe solution was washed with water, brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customEvaporation of the solvent
  5. customprovided a foam which
  6. customwas purified by flash chromatography (7% methanol in dichloromethane)
  7. customThe product was crystallized from acetonitrile-isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-f78e2d7279a34a54a79cf6d7d830d5ac
Quelldatensatz
uspto-grants-1988_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04746656

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