Potassium Carbonate → 4-nitro-2-(1H-1,2,4-triazol-1-yl)pyridine 1-oxide

HRID 1640108

Reaction equation

HRID 1640108 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][N+:3]=1[O-:11].C[Si](C)(C)[N:14]1[CH:18]=[N:17][CH:16]=[N:15]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N+:8]([C:6]1[CH:5]=[CH:4][N+:3]([O-:11])=[C:2]([N:14]2[CH:18]=[N:17][CH:16]=[N:15]2)[CH:7]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 844332-Chloro-4-nitropyridine 1-oxideHCID 875581-Trimethylsilyl-1,2,4-triazole

Product 1

HCID 667213864-nitro-2-(1H-1,2,4-triazol-1-yl)pyridine 1-oxideYield 27.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-chloro-4-nitropyridine 1-oxide (2.00 g, 11.4 mmol) and 1-(trimethylsilyl)-1H-1,2,4-triazole (1.64 mL, 11.4 mmol) in DMF (40 mL), was added potassium carbonate (4.75 g, 34.4 mmol). The reaction mixture was allowed to stir at rt for 2 h. The DMF was evaporated and water was added. The precipitate was filtered and washed with water then hexane and dried under vacuum. The solid was purified by column to give 4-nitro-2-(1H-1,2,4-triazol-1-yl)pyridine 1-oxide (0.643 g, 27.1%) as a pale yellow solid. LCMS: (FA) ES+ 208.1, ES− 206.1.

Workup

  1. customThe DMF was evaporated
  2. additionwater was added
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. dry with materialhexane and dried under vacuum
  6. customThe solid was purified by column

Sources & evidence

ORD record
ord-f5ff02d794014095bf81206b1d4540ab
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Linked notes

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