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Semicarbazide hydrochloride → 6-(4-Fluorophenyl)-1,2,4-triazin-3(2H)-one

HRID 500104
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 500104
C(O[CH:4](OCC)[C:5]([C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1)=O)C.Cl.[NH2:18][NH:19][C:20]([NH2:22])=[O:21]>C(O)C>[F:13][C:10]1[CH:9]=[CH:8][C:7]([C:5]2[CH:4]=[N:22][C:20](=[O:21])[NH:19][N:18]=2)=[CH:12][CH:11]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 11236Semicarbazide hydrochlorideHCID 224161332,2-Diethoxy-1-(4-fluorophenyl)ethanone

Produkt 1

HCID 125812846-(4-Fluorophenyl)-1,2,4-triazin-3(2H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 2,2-diethoxy-1-(4-fluorophenyl)ethanone (5.2 g, 23 mmol), semicarbazide hydrochloride (2.6 g, 24 mmol) in ethanol (50 mL) was stirred overnight at ambient temperature and then heated to 80° C. for 5 hours. The reaction mixture was concentrated and the resulting residue was dissolved in acetic acid (50 mL) which was heated to 130° C. for 6 h. After cooling, the mixture was concentrated under reduced pressure. The residue was triturated with ethyl ether, filtered, and washed with diethyl ether and then hexanes. The crystalline material was collected and dried under high vacuum to give the desired product. (4.2 g, 96%) LCMS: (M+H)=192.1.

Aufarbeitung

  1. temperatureheated to 80° C. for 5 hours
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe resulting residue was dissolved in acetic acid (50 mL) which
  4. temperaturewas heated to 130° C. for 6 h
  5. temperatureAfter cooling
  6. concentrationthe mixture was concentrated under reduced pressure
  7. customThe residue was triturated with ethyl ether
  8. filtrationfiltered
  9. washwashed with diethyl ether
  10. customThe crystalline material was collected
  11. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-7ef1b21d62884fc29070255c63f2aa87
Quelldatensatz
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07767675B2

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