Ethyl Acetate → (1-ethylpyrazol-5-yl) 2,4-dichloro-3-(1-methyl-3-methylcarbonyl-1H-pyrazol-5-yl)benzoate

HRID 1276127

Reaktionsgleichung

Reaktionsgleichung von HRID 1276127
[CH2:1]([N:3]1[C:7]([OH:8])=[CH:6][CH:5]=[N:4]1)[CH3:2].[Cl:9][C:10]1[C:18]([C:19]2[N:23]([CH3:24])[N:22]=[C:21]([C:25]([CH3:27])=[O:26])[CH:20]=2)=[C:17]([Cl:28])[CH:16]=[CH:15][C:11]=1[C:12](O)=[O:13].C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>C(#N)C>[Cl:9][C:10]1[C:18]([C:19]2[N:23]([CH3:24])[N:22]=[C:21]([C:25]([CH3:27])=[O:26])[CH:20]=2)=[C:17]([Cl:28])[CH:16]=[CH:15][C:11]=1[C:12]([O:8][C:7]1[N:3]([CH2:1][CH3:2])[N:4]=[CH:5][CH:6]=1)=[O:13]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 221149072,4-dichloro-3-(1-methyl-3-methylcarbonyl-1H-pyrazol-5-yl)benzoic acidHCID 178418331HCID 178418331, Verbindung

Produkt 1

HCID 53727367(1-ethylpyrazol-5-yl) 2,4-dichloro-3-(1-methyl-3-methylcarbonyl-1H-pyrazol-5-yl)benzoateAusbeute 27,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

0.21 g (1.9 mmol) of 1-ethyl-5-hydroxy-1H-pyrazole and 0.39 g (1.9 mmol) of N,N-dicyclohexylcarbodiimide were added to 0.59 g (1.9 mmol) of 2,4-dichloro-3-(1-methyl-3-methylcarbonyl-1H-pyrazol-5-yl)benzoic acid in 8 ml of acetonitrile. The mixture was stirred at room temperature for 12 hours and 25 ml of 5% strength sodium carbonate solution and 50 ml of ethyl acetate were added, insoluble components were filtered off and the organic phase was separated off, dried and concentrated. The residue was subsequently chromatographed over silica gel (eluent: ethyl acetate:cyclohexane=1:1). 0.21 g (27% of theory) of (1-ethylpyrazol-5-yl) 2,4-dichloro-3-(1-methyl-3-methylcarbonyl-1H-pyrazol-5-yl)benzoate was obtained.

Aufarbeitung

  1. filtrationinsoluble components were filtered off
  2. customthe organic phase was separated off
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was subsequently chromatographed over silica gel (eluent: ethyl acetate:cyclohexane=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-01b944fcd4c8489082f50d481062d0ff
Quelldatensatz
uspto-grants-2000_12
Patentnummer
US06165944

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