Butanoic acid, 2,3-dibromo-, ethyl ester → 2-benzylsulfanyl-7-methyl-1H-[1,2,4]triazolo[1,5-a]pyrimidin-5-one

HRID 477217

Reaktionsgleichung

Reaktionsgleichung von HRID 477217
Br[CH:2]([CH:8](Br)[CH3:9])[C:3]([O:5]CC)=O.[NH2:11][C:12]1[N:16]=[C:15]([S:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[NH:14][N:13]=1>N1C=CC=CC=1>[CH2:18]([S:17][C:15]1[N:16]=[C:12]2[N:11]=[C:3]([OH:5])[CH:2]=[C:8]([CH3:9])[N:13]2[N:14]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Komponenten

4

Edukt 2

HCID 98157Butanoic acid, 2,3-dibromo-, ethyl esterHCID 178509291HCID 178509291, Verbindung

Produkt 1

HCID 1784292742-benzylsulfanyl-7-methyl-1H-[1,2,4]triazolo[1,5-a]pyrimidin-5-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

Ethyl 2,3-dibromobutyrate (1.33 g, 48.5 mmol) was added dropwise over 15 minutes to a solution of 10 g (49 mmol) of 3-amino-5-benzylthio-1,2,4-triazole in 20 ml of pyridine heated to 65° C. After the addition was complete, the reaction mixture was heated at 65° C. for 20 hours, cooled to room temperature and filtered. The filtrate was concentrated by evaporation at reduced pressure. The residue was triturated with methanol to separate 1.64 g (13%) of the desired product as a colorless crystalline solid, m.p. 219°-220° C. IR and 1H NMR spectra were in agreement with the assigned structure.

Aufarbeitung

  1. additionAfter the addition
  2. temperaturethe reaction mixture was heated at 65° C. for 20 hours
  3. temperaturecooled to room temperature
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated by evaporation at reduced pressure
  6. customThe residue was triturated with methanol
  7. customto separate 1.64 g (13%) of the desired product as a colorless crystalline solid, m.p. 219°-220° C

Quellen und Nachweise

ORD-Eintrag
ord-aa77b9a59e7b482c80ef58849dfeb3b7
Quelldatensatz
uspto-grants-1989_12
Patentnummer
US04886883

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