Dimethylformamide → Ethyl [(4-formyl-1,3-dimethyl-1H-pyrazol-5-yl)sulfanyl]acetate

HRID 534816Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 534816
Cl[C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH3:8])[C:3]=1[CH:9]=[O:10].[C:11]([O:15][CH2:16][CH3:17])(=[O:14])[CH2:12][SH:13].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH:9]([C:3]1[C:4]([CH3:8])=[N:5][N:6]([CH3:7])[C:2]=1[S:13][CH2:12][C:11]([O:15][CH2:16][CH3:17])=[O:14])=[O:10]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 12185Ethyl ThioglycolateHCID 27773975-Chloro-1,3-dimethylpyrazole-4-carboxaldehyde

Produkt 1

HCID 63802037Ethyl [(4-formyl-1,3-dimethyl-1H-pyrazol-5-yl)sulfanyl]acetateAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 5-chloro-1,3-dimethyl-1H-pyrazole-4-carbaldehyde (5.0 g), ethyl thioglycolate (3.97 g), potassium carbonate (5.53 g), and N,N-dimethylformamide (150 mL) was stirred at 80° C. for over-night. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by flash column chromatography (silica gel, 90:10-50:50 hexane/ethyl acetate) to provide the title compound (2.12 g, 28%) as an oil.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by flash column chromatography (silica gel, 90:10-50:50 hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-999bf2ae987c468a98364e5d7f0d8ad4
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853215B2

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