Chloroform → 1-methyl-5-nitro-3-(2H-1,2,3-triazol-2-yl)pyridin-2(1H)-one

HRID 340484Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 340484
CI.[CH:3](Cl)(Cl)Cl.[N+:7]([C:10]1[CH:11]=[C:12]([N:17]2[N:21]=[CH:20][CH:19]=[N:18]2)[C:13]([OH:16])=[N:14][CH:15]=1)([O-:9])=[O:8].[N+:22]([C:25]1[CH:26]=[C:27]([N:32]2[CH:36]=[CH:35][N:34]=[N:33]2)[C:28]([OH:31])=[N:29][CH:30]=1)([O-:24])=[O:23]>C(=O)([O-])[O-].[Ag+2].O>[CH3:25][N:14]1[CH:15]=[C:10]([N+:7]([O-:9])=[O:8])[CH:11]=[C:12]([N:17]2[N:21]=[CH:20][CH:19]=[N:18]2)[C:13]1=[O:16].[CH3:3][N:29]1[CH:30]=[C:25]([N+:22]([O-:24])=[O:23])[CH:26]=[C:27]([N:32]2[CH:36]=[CH:35][N:34]=[N:33]2)[C:28]1=[O:31]

Komponenten

8

Edukt 4

HCID 6212ChloroformHCID 6328Methyl iodideHCID 1785268425-nitro-3-(1H-1,2,3-triazol-1-yl)pyridin-2-olHCID 178526843HCID 178526843, Verbindung

Produkt 2

HCID 866838671-methyl-5-nitro-3-(2H-1,2,3-triazol-2-yl)pyridin-2(1H)-oneHCID 866838681-methyl-5-nitro-3-(1H-1,2,3-triazol-1-yl)pyridin-2(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418647HCID 178418647, VerbindungKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

Silver carbonate (377 mg) and methyl iodide (366 W) were added to a chloroform (10 ml) solution containing the mixture of 5-nitro-3-(2H-1,2,3-triazol-2-yl)pyridin-2-ol and 5-nitro-3-(1H-1,2,3-triazol-1-yl)pyridin-2-ol (184 mg) obtained in the 1st step while shielding light, followed by reflux for 2 hours. Water was added, followed by extraction with ethyl acetate. The resultant was washed with saturated saline and dried over anhydrous sodium sulfate. Subsequently, the solvent was distilled away under reduced pressure, the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=2:5 to 2:3), and a white solid of 1-methyl-5-nitro-3-(2H-1,2,3-triazol-2-yl)pyridin-2(1H)-one (28.1 mg) and a white solid of 1-methyl-5-nitro-3-(1H-1,2,3-triazol-1-yl)pyridin-2(1H)-one (23.3 mg) were thus obtained.

Aufarbeitung

  1. additioncontaining
  2. customobtained in the 1st step
  3. temperatureby reflux for 2 hours
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe resultant was washed with saturated saline
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationSubsequently, the solvent was distilled away under reduced pressure
  8. customthe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=2:5 to 2:3)

Quellen und Nachweise

ORD-Eintrag
ord-a59a8f0990b54308938cb14c13ae5dfe
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895585B2

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