Triethylamine → HCID 178503424, Verbindung

HRID 2359029Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2359029
C[N:2](C)[CH:3]=[C:4]([C:13]1[CH:18]=[CH:17][N:16]=[C:15]([S:19][CH3:20])[N:14]=1)[C:5]([C:7]1[S:8][C:9]([Cl:12])=[CH:10][CH:11]=1)=O.O.NN.C([N:27](CC)CC)C>C(O)C.O>[Cl:12][C:9]1[S:8][C:7]([C:5]2[C:4]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([S:19][CH3:20])[N:14]=3)=[CH:3][NH:2][N:27]=2)=[CH:11][CH:10]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 67261197HCID 67261197, Verbindung

Produkt 1

HCID 178503424HCID 178503424, VerbindungAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a mixture of 3-(dimethylamino)-1-(5-chloro-2-thienyl)-2-[2-(methylsulfanyl)pyrimidin-4-yl]prop-2-en-1-one (1 eq, 96 mmol) in 300 mL ethanol was added dropwise hydrazine hydrate (1.5 eq, 144 mmol) and then triethylamine (1.5 eq, 144 mmol). The mixture was heated under reflux for 2 h and then overnight at room temperature. The solvent was then slowly poured in 1 L of water. The resulting precipitate was filtered and dried to afford 24 g of 4-[3-(5-chloro-2-thienyl)-1H-pyrazol-4-yl]-2-(methylsulfanyl)pyrimidine (80% yield).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 h
  3. customovernight
  4. customat room temperature
  5. filtrationThe resulting precipitate was filtered
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-1a365012950c44fc84e93bc8fdf2f431
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08685974B2

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