Ethyl Methanesulfonate → 3,5-dibromo-1-ethyl-1H-1,2,4-triazole

HRID 1054976Notes

Reaction equation

HRID 1054976 reaction equation
[Br:1][C:2]1[N:6]=[C:5]([Br:7])[NH:4][N:3]=1.[H-].[Na+].CS(O[CH2:15][CH3:16])(=O)=O>CN(C)C=O.O>[Br:1][C:2]1[N:6]=[C:5]([Br:7])[N:4]([CH2:15][CH3:16])[N:3]=1

Participants

6

Reactant 3

HCID 6113Ethyl MethanesulfonateHCID 24758Sodium hydrideHCID 819043,5-Dibromo-4H-1,2,4-triazole

Product 1

HCID 450329603,5-dibromo-1-ethyl-1H-1,2,4-triazoleYield 90.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

3,5-Dibromo-1H-1,2,4-triazole (2.5 g, 11.0 mmol, Eq: 1.00) was dissolved in dimethylformamide (31.8 ml) and sodium hydride (529 mg, 60% dispersion in mineral oil, 13.2 mmol, Eq: 1.2) was added slowly. Ethyl methanesulfonate (2.74 g, 2.27 ml, 22.0 mmol, Eq: 2) was added to the reaction and the mixture was heated in a microwave oven for 60 minutes at 100° C. The mixture was diluted with water and extracted 3× with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and the solvent was evaporated to give 3,5-dibromo-1-ethyl-1H-[1,2,4]triazole (2.54 g, 90.4%) as a white powder. MS: m/z=255.9 (M+H+)

Workup

  1. extractionextracted 3× with ethyl acetate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-140b732109d9451fbcc1d8a14965af0d
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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