Ethyl benzoylacetate → 2-(3,5-Dichloro-phenyl)-5-phenyl-2,4-dihydro-pyrazol-3-one

HRID 2187398Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2187398
[C:1]([CH2:9][C:10]([O:12]CC)=O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[Cl:16][C:17]1[CH:18]=[C:19]([NH:24][NH2:25])[CH:20]=[C:21]([Cl:23])[CH:22]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[Cl:16][C:17]1[CH:18]=[C:19]([N:24]2[C:10](=[O:12])[CH2:9][C:1]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[N:25]2)[CH:20]=[C:21]([Cl:23])[CH:22]=1

Komponenten

5

Edukt 3

HCID 7170Ethyl benzoylacetateHCID 521998p-Toluenesulfonic acid monohydrateHCID 2723913(3,5-Dichlorophenyl)hydrazine monohydrochloride

Produkt 1

HCID 120499692-(3,5-Dichloro-phenyl)-5-phenyl-2,4-dihydro-pyrazol-3-oneAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of ethyl benzoylacetate (0.192 g, 1.00 mmol), 3,5-dichlorophenylhydrazine hydrochloride (0.235 g, 1.10 mmol), and p-toluenesulfonic acid monohydrate (0.019 g, 0.10 mmol) in ethanol (10 mL) was heated at reflux for 24 hours. The reaction solution was concentrated and the resulting residue was partitioned between ethyl acetate and aqueous 1N hydrochloric acid solution. The organic layer was further washed with water and brine, dried (sodium sulfate) and concentrated to afford a yellow solid. The crude product was triturated with hexanes and collected by suction filtration. Air drying afforded 0.174 g (57%) of product as a bright yellow solid: 1H NMR (DMSO-d6) δ12.60-12.40 (br s, 1H), 7.92 (s, 2H), 7.87-7.83 (d, 2H), 7.50 (s, 1H), 7.44-7.38 (m, 2H), 7.36-7.31 (m, 1H), 6.02 (s, 1H) ppm.

Aufarbeitung

  1. temperatureat reflux for 24 hours
  2. concentrationThe reaction solution was concentrated
  3. customthe resulting residue was partitioned between ethyl acetate and aqueous 1N hydrochloric acid solution
  4. washThe organic layer was further washed with water and brine
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated
  7. customto afford a yellow solid
  8. customThe crude product was triturated with hexanes
  9. filtrationcollected by suction filtration
  10. customAir drying

Quellen und Nachweise

ORD-Eintrag
ord-291e57aaa3304f20bada8d4c01da3006
Quelldatensatz
uspto-grants-2002_06
Patentnummer
US06410533B1

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