Sodium Chloride → 5-(5-Pyrimidylmethyloxy)-3-methylthio-1,2,4-thiadiazole

HRID 917338Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 917338
Cl[C:2]1[S:6][N:5]=[C:4]([S:7][CH3:8])[N:3]=1.[N:9]1[CH:14]=[C:13]([CH2:15][OH:16])[CH:12]=[N:11][CH:10]=1.[H-].[Na+].[Cl-].[Na+]>CN(C)C=O>[N:9]1[CH:14]=[C:13]([CH2:15][O:16][C:2]2[S:6][N:5]=[C:4]([S:7][CH3:8])[N:3]=2)[CH:12]=[N:11][CH:10]=1

Komponenten

6

Edukt 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 5709535-Chloro-3-(methylsulfanyl)-1,2,4-thiadiazoleHCID 15466386(Pyrimidin-5-yl)methanol

Produkt 1

HCID 230324625-(5-Pyrimidylmethyloxy)-3-methylthio-1,2,4-thiadiazoleAusbeute 48,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Into 4 g of N,N-dimethylformamide were dissolved 304 mg of 5-chloro-3-methylthio-1,2,4-thiadiazole and 200 mg of 5-pyrimidylmethyl alcohol, 97 mg of sodium hydride (60% in oil) was added thereto under ice-cooling, and the reaction mixture was stirred for 30 minutes. After stirring for 5 hours at room temperature, the reaction mixture was added to saturated sodium chloride aqueous solution, and extracted with t-butyl methyl ether. The organic layer was concentrated, and the residue obtained was subjected to silica gel column chromatography to give 210 mg of 5-(5-pyrimidylmethyloxy)-3-methylthio-1,2,4-thiadiazole (hereinafter, referred to as the present compound (37)).

Aufarbeitung

  1. additionwas added
  2. temperatureunder ice-cooling
  3. stirringAfter stirring for 5 hours at room temperature
  4. extractionextracted with t-butyl methyl ether
  5. concentrationThe organic layer was concentrated
  6. customthe residue obtained

Quellen und Nachweise

ORD-Eintrag
ord-8bc17690d3274f30b06863909a02493a
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07273879B2

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