Hydrochloric Acid → 5-(2,6-difluorobenzyl)-4-methyl-4H-1,2,4-triazole-3-carboxamide

HRID 2372404Notes

Reaction equation

HRID 2372404 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:3]=1[CH2:4][C:5]1[N:6]([CH3:12])[C:7]([CH2:10][OH:11])=[N:8][N:9]=1.O.Cl.[C-]#[N:21].[Na+]>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[F:17][C:13]1[CH:14]=[CH:15][CH:16]=[C:2]([F:1])[C:3]=1[CH2:4][C:5]1[N:6]([CH3:12])[C:7]([C:10]([NH2:21])=[O:11])=[N:8][N:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8929Sodium CyanideHCID 199042335-(2,6-difluorobenzyl)-3-hydroxymethyl-4-methyl-4H-1,2,4-triazole

Product 1

HCID 199042355-(2,6-difluorobenzyl)-4-methyl-4H-1,2,4-triazole-3-carboxamide

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 1140TolueneSolvent

Procedure

1.43 g (6 mmol) of 5-(2,6-difluorobenzyl)-3-hydroxymethyl-4-methyl-4H-1,2,4-triazole and 5.22 g (60 mmol) of manganese dioxide are heated under reflux in 40 ml of toluene for 3 hours using a water separator. The reaction mixture is then cooled and filtered over Hyflo, and the filtrate is concentrated by evaporation. The residue is added to 90 ml of isopropanol saturated with ammonia. At 0°, 1 47 g (30 mmol) of sodium cyanide and 10.44 g (120 mmol) of manganese dioxide are added. The reaction mixture is stirred for 4 hours at 0° and filtered over Hyflo. The filtrate is concentrated by evaporation. Recrystallisation of the residue from ethanol yields the pure 5-(2,6-difluorobenzyl)-4-methyl-4H-1,2,4-triazole-3-carboxamide

Workup

  1. temperatureThe reaction mixture is then cooled
  2. filtrationfiltered over Hyflo
  3. concentrationthe filtrate is concentrated by evaporation
  4. additionThe residue is added to 90 ml of isopropanol saturated with ammonia
  5. filtrationfiltered over Hyflo
  6. concentrationThe filtrate is concentrated by evaporation
  7. customRecrystallisation of the residue from ethanol

Sources & evidence

ORD record
ord-291467b930b44cad92c8c6ec6f629f5e
Source dataset
uspto-grants-1992_03
Patent number
US05098922

Reaction notes

Loading…