Thionyl Chloride → 2-chloro-5-nitro-3-(2H-1,2,3-triazol-2-yl)pyridine

HRID 340488Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 340488
S(Cl)([Cl:3])=O.O[C:6]1[C:11]([N:12]2[N:16]=[CH:15][CH:14]=[N:13]2)=[CH:10][C:9]([N+:17]([O-:19])=[O:18])=[CH:8][N:7]=1.O[C:21]1[C:26]([N:27]2[CH:31]=[CH:30][N:29]=[N:28]2)=[CH:25][C:24]([N+:32]([O-:34])=[O:33])=[CH:23][N:22]=1>CN(C=O)C>[Cl:3][C:6]1[C:11]([N:12]2[N:16]=[CH:15][CH:14]=[N:13]2)=[CH:10][C:9]([N+:17]([O-:19])=[O:18])=[CH:8][N:7]=1.[Cl:3][C:21]1[C:26]([N:27]2[CH:31]=[CH:30][N:29]=[N:28]2)=[CH:25][C:24]([N+:32]([O-:34])=[O:33])=[CH:23][N:22]=1

Komponenten

6

Edukt 3

HCID 24386Thionyl ChlorideHCID 1785268425-nitro-3-(1H-1,2,3-triazol-1-yl)pyridin-2-olHCID 178526843HCID 178526843, Verbindung

Produkt 2

HCID 866838702-chloro-5-nitro-3-(2H-1,2,3-triazol-2-yl)pyridineHCID 866838712-chloro-5-nitro-3-(1H-1,2,3-triazol-1-yl)pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Thionyl chloride (3.9 ml) and DMF (0.39 ml) were added to a mixture of 2-hydroxy-5-nitro-3-(2H-1,2,3-triazol-2-yl)pyridine and 2-hydroxy-5-nitro-3-(1H-1,2,3-triazol-1-yl)pyridine (385 mg), followed by stirring at 90° C. for 2 hours. The reaction solution was adjusted to room temperature, slowly added to ice water, and stirred under ice cooling for 30 minutes, followed by extraction with ethyl acetate. Then, the resultant was washed with saturated saline and dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure, the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=9:1 to 2:1), and a yellow solid of 2-chloro-5-nitro-3-(2H-1,2,3-triazol-2-yl)pyridine (177 mg) and a yellow solid of 2-chloro-5-nitro-3-(1H-1,2,3-triazol-1-yl)pyridine (83 mg) were thus obtained.

Aufarbeitung

  1. customwas adjusted to room temperature
  2. stirringstirred under ice cooling for 30 minutes
  3. extractionfollowed by extraction with ethyl acetate
  4. washThen, the resultant was washed with saturated saline
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled away under reduced pressure
  7. customthe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=9:1 to 2:1)

Quellen und Nachweise

ORD-Eintrag
ord-d9f4c3ccc9e442fe89855f97ca467ed0
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895585B2

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