Methanol → 1-(2,6-Difluorobenzyl)-1H-1,2,3-triazole-4-carboxyamide

HRID 218815Notes

Reaction equation

HRID 218815 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:3]=1[CH2:4][N:5]1[CH:9]=[C:8]([C:10](OC)=O)[N:7]=[N:6]1.[NH4+:19].[OH-:20].[CH3:21]O>O>[F:18][C:14]1[CH:15]=[CH:16][CH:17]=[C:2]([F:1])[C:3]=1[CH2:4][N:5]1[CH:9]=[C:8]([CH2:10][C:21]([NH2:19])=[O:20])[N:7]=[N:6]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14923Ammonium HydroxideHCID 22716778CGP-47292 methyl ester

Product 1

HCID 1317297751-(2,6-Difluorobenzyl)-1H-1,2,3-triazole-4-carboxyamideYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

Methyl 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylate (II) (10.6 g, 41.9 mmoles), prepared as reported in Example 7, is dissolved in methanol (10 ml) and treated at room temperature under stirring with a 30% ammonia aqueous solution (40 ml), then the reaction mixture is refluxed and kept under stirring for 3 hours. The mixture is cooled to 20° C., then diluted with water, filtered, and the resulting white solid is washed with water and dried in a static dryer at 50° C. Rufinamide (8.7 g) is obtained as a crystalline white solid in 87% yield.

Workup

  1. additiontreated at room temperature
  2. temperaturethe reaction mixture is refluxed
  3. filtrationfiltered
  4. washthe resulting white solid is washed with water
  5. customdried in a static dryer at 50° C

Sources & evidence

ORD record
ord-1f9b864bb9044e54a11883ad9405afb8
Source dataset
uspto-grants-2012_06
Patent number
US08198459B2

Reaction notes

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