Dimethyl malonate → 2-benzylsulfanyl-7-hydroxy-1H-[1,2,4]triazolo[1,5-a]pyrimidin-5-one

HRID 1251977

Reaktionsgleichung

Reaktionsgleichung von HRID 1251977
C[O-].[Na+].[C:4]([O:11]C)(=O)[CH2:5][C:6](OC)=[O:7].[NH2:13][C:14]1[N:18]=[C:17]([S:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[NH:16][N:15]=1>CO.C(O)C>[CH2:20]([S:19][C:17]1[N:18]=[C:14]2[N:13]=[C:4]([OH:11])[CH:5]=[C:6]([OH:7])[N:15]2[N:16]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Komponenten

6

Edukt 3

HCID 7943Dimethyl malonateHCID 10942334Sodium MethoxideHCID 178509291HCID 178509291, Verbindung

Produkt 1

HCID 1785166162-benzylsulfanyl-7-hydroxy-1H-[1,2,4]triazolo[1,5-a]pyrimidin-5-oneAusbeute 127,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 125 g (0.58 mol) of a 25% solution of sodium methoxide in methanol dissolved in 100 ml of absolute ethanol was treated with 66.3 ml (0.29 mol) of dimethyl malonate followed by 60.0 g (0.20 mol) of 3-amino-5-benzylthio-1,2,4-triazole. The resulting solution was heated at reflux for 5 days. On cooling to room temperature the solid which had separated was collected by filtration, washed with cold ethanol and dissolved in 1000 ml of water. The resulting yellow solution was acidified with concentrated HCl to precipitate a solid. The solid was collected by filtration and dried to yield 70.1 g (82%) of the desired product as a white solid, m.p. 199°-210° C. (decomposition). IR and 1H NMR spectra were in agreement with the assigned structure.

Aufarbeitung

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for 5 days
  3. customhad separated
  4. filtrationwas collected by filtration
  5. washwashed with cold ethanol
  6. dissolutiondissolved in 1000 ml of water
  7. customto precipitate a solid
  8. filtrationThe solid was collected by filtration
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-23dd15557f324f84b7c1935fff1f2693
Quelldatensatz
uspto-grants-1988_05
Patentnummer
US04741764

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