Potassium Acetate → 1-Acetyl-1H-thieno[2,3-c]pyrazole-5-carbonitrile

HRID 34074

Reaktionsgleichung

Reaktionsgleichung von HRID 34074
Cl[C:2]1[S:3][C:4]([C:13]#[N:14])=[CH:5][C:6]=1[CH:7]=[N:8][NH:9][C:10](=[O:12])[CH3:11].C([O-])(=O)C.[K+]>C1(OC2C=CC=CC=2)C=CC=CC=1.[Cu]>[C:10]([N:9]1[C:2]2[S:3][C:4]([C:13]#[N:14])=[CH:5][C:6]=2[CH:7]=[N:8]1)(=[O:12])[CH3:11]

Komponenten

5

Edukt 2

HCID 517044Potassium AcetateHCID 68929248Acetic acid (2-chloro-5-cyanothiophen-3-ylmethylene)hydrazide

Produkt 1

HCID 689272371-Acetyl-1H-thieno[2,3-c]pyrazole-5-carbonitrileAusbeute 10,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23978CopperKatalysatorHCID 7583Diphenyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

To a solution of 2.53 g of acetic acid (2-chloro-5-cyanothiophen-3-ylmethylene)hydrazide in 22 mL of diphenyl ether were added copper powder and potassium acetate at room temperature, and stirred at 200° C. for 6 hours. Following filtration through Celite, the filtrate was washed successively with saturated aqueous ammonium chloride and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The crude product was purified and separated by silica gel column chromatography (ethyl acetate:n-hexane=1:10-1:5), to afford 215 mg of the title compound as colorless crystals.

Aufarbeitung

  1. filtrationfiltration through Celite
  2. washthe filtrate was washed successively with saturated aqueous ammonium chloride and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customThe crude product was purified
  6. customseparated by silica gel column chromatography (ethyl acetate:n-hexane=1:10-1:5)

Quellen und Nachweise

ORD-Eintrag
ord-9364f7cbd9224c62904bb2461f3a280e
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07429609B2

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