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

HRID 1251970Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1251970
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-fb1b58d105354d22a6b3bb6289f4f725
Quelldatensatz
uspto-grants-1988_05
Patentnummer
US04741764

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