Sodium → 2-Benzylthio-5,6-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine

HRID 1031346

Reaktionsgleichung

Reaktionsgleichung von HRID 1031346
[NH2:1][C:2]1[N:6]=[C:5]([S:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:4][N:3]=1.[Na].[CH3:16][CH:17]([C:20](=O)[CH3:21])[CH:18]=O>C(O)(=O)C>[CH2:8]([S:7][C:5]1[N:6]=[C:2]2[N:1]=[C:20]([CH3:21])[C:17]([CH3:18])=[CH:16][N:3]2[N:4]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Komponenten

5

Edukt 3

HCID 5360545SodiumHCID 11051586Butanal, 2-methyl-3-oxo-HCID 178509291HCID 178509291, Verbindung

Produkt 1

HCID 141550922-Benzylthio-5,6-dimethyl-1,2,4-triazolo[1,5-a]pyrimidineAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A solution of 5.0 g (24 mmol) of 3-amino-5-benzylthio-1,2,4-triazole and 5.0 g (41 mmol) of the sodium salt of 2-methyl-3-oxobutanal in 200 ml of glacial acetic acid was heated at reflux overnight. The solution was cooled to room temperature and the reaction mixture was concentrated by evaporation at reduced pressure. The residue was combined with ice and H2O to separate a tan solid. The solid was collected by filtration, dried and carefully recrystallized from ethyl acetate to yield 3.53 g (54%) of the desired product as a crystalline solid, m.p. 147°-149° C. IR and 1H NMR spectra were in agreement with the assigned structure.

Aufarbeitung

  1. temperatureat reflux overnight
  2. concentrationthe reaction mixture was concentrated by evaporation at reduced pressure
  3. customto separate a tan solid
  4. filtrationThe solid was collected by filtration
  5. customdried
  6. customcarefully recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-62a8068cf4c0480e8f7eba75178ad228
Quelldatensatz
uspto-grants-1990_09
Patentnummer
US04954163

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