StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Triethylamine → HCID 67260280, Verbindung

HRID 2359027
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2359027
[Cl:1][C:2]1[S:6][C:5]([C:7](=O)[CH2:8][C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[CH:16]([NH:20][NH2:21])([CH2:18][CH3:19])[CH3:17].[CH2:22](N(CC)CC)C>ClCCl>[CH:16]([N:20]1[CH:22]=[C:8]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[C:7]([C:5]2[S:6][C:2]([Cl:1])=[CH:3][CH:4]=2)=[N:21]1)([CH2:18][CH3:19])[CH3:17].[CH:16]([N:20]1[C:7]([C:5]2[S:6][C:2]([Cl:1])=[CH:3][CH:4]=2)=[C:8]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[CH:22]=[N:21]1)([CH2:18][CH3:19])[CH3:17]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 547690sec-ButylhydrazineHCID 65583291HCID 65583291, Verbindung

Produkt 2

HCID 67260280HCID 67260280, VerbindungAusbeute 21 %HCID 67260571HCID 67260571, VerbindungAusbeute 16 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

A mixture of 1-(5-chloro-2-thienyl)-2-(pyridin-4-yl)ethanone (0.68 mmol), secbutylhydrazin (1.37 mmol) and triethylamine (1.37 mmol) in 5 mL dichloromethane was refluxed for 2.5 h. The solvent was evaporated under reduced pressure and the residue was partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate and the combined organic extracts were dried over MgSO4 filtered and concentrated. The residue was purified by chromatography on silica gel (dichloromethane:methanol 100:1 to 20:1) to afford 37 mg of 4-[1-sec-butyl-3-(5-chloro-2-thienyl)-1H-pyrazol-4-yl]pyridine (16% yield) and 48 mg of 4-[1-sec-butyl-5-(5-chloro-2-thienyl)-1H-pyrazol-4-yl]pyridine (21% yield).

Aufarbeitung

  1. temperaturewas refluxed for 2.5 h
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was partitioned between ethyl acetate and water
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. dry with materialthe combined organic extracts were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography on silica gel (dichloromethane:methanol 100:1 to 20:1)

Quellen und Nachweise

ORD-Eintrag
ord-836c52c166684ccfa282695d0e5143ee
Quelldatensatz
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08685974B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion