Water → 5-bromo-1-methyl-3-nitro-1H-1,2,4-triazole

HRID 910306Notes

Reaction equation

HRID 910306 reaction equation
[H-].[Na+].[Br:3][C:4]1[NH:8][N:7]=[C:6]([N+:9]([O-:11])=[O:10])[N:5]=1.[CH3:12]I.O>CN(C)C=O>[Br:3][C:4]1[N:8]([CH3:12])[N:7]=[C:6]([N+:9]([O-:11])=[O:10])[N:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178526904HCID 178526904, compound

Product 1

HCID 27720935-bromo-1-methyl-3-nitro-1H-1,2,4-triazoleYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

1.1 g (28.5 mmol) of 60% sodium hydride are added to a solution of 5 g (25.9 mmol) of 5-bromo-3-nitro-1H-[1,2,4]-triazole in 80 ml of dimethylformamide, cooled beforehand to 0° C. The reaction medium is stirred for 20 minutes and 8 ml (129.5 mmol) of methyl iodide are then added. After stirring at room temperature for 18 hours, water is added and the reaction medium is extracted with ethyl acetate. The organic phase is washed thoroughly with water, with saturated sodium chloride solution, dried over magnesium sulfate, filtered and evaporated. The residue obtained is purified by thin-layer chromatography on silica eluted with a 75/25 heptane/ethyl acetate mixture. 3.2 g (60%) of 5-bromo-1-methyl-3-nitro-1H-[1,2,4]triazole are obtained.

Workup

  1. stirringAfter stirring at room temperature for 18 hours
  2. extractionthe reaction medium is extracted with ethyl acetate
  3. washThe organic phase is washed thoroughly with water, with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue obtained
  8. customis purified by thin-layer chromatography on silica
  9. washeluted with a 75/25 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-3b8f60f356dc459992d34fd87ae93adc
Source dataset
uspto-grants-2011_09
Patent number
US08022079B2

Reaction notes

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