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

HRID 1620091Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1620091
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-2ec20bb790d641ad8429ca22df11c8d4
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772320B2

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