Methyl iodide → 3-(2-Fluorophenyl)-4-methyl-5-(methylsulfanyl)-4H-1,2,4-triazole

HRID 703126Notes

Reaction equation

HRID 703126 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([CH3:14])[C:10](=[S:13])[NH:11][N:12]=1.[C:15]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([CH3:14])[C:10]([S:13][CH3:15])=[N:11][N:12]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 974966HCID 974966, compound

Product 1

HCID 30879983-(2-Fluorophenyl)-4-methyl-5-(methylsulfanyl)-4H-1,2,4-triazoleYield 73%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 5-(2-fluorophenyl)-2 4-dihydro-4-methyl-3H-1,2,4-triazole-3-thione (4.56 g 2.18×10-2 mole), K2CO3 (3.01 g, 2.18×10-2 mole), methyl iodide (1 5 ml 2.4×10-2 mole), and acetone (65 ml) was stirred and warmed to reflux. After refluxing overnight, the solvent was evaporated and the concentrate was treated with water. The aqueous mixture was extracted three times with EtOAc. The EtOAc extracts were combined washed with saturated aqueous NaCl, and dried over anhydrous Na2SO4. The drying agent was removed by filtration and the filtrate was evaporated at reduced pressure affording a pale yellow oil which was purified by chromatography and kugel rohr distillation, affording a pale yellow oil 3.55 g (73%), bp=190°-197° C. (0.3 mm).

Workup

  1. temperaturewarmed to reflux
  2. temperatureAfter refluxing overnight
  3. customthe solvent was evaporated
  4. additionthe concentrate was treated with water
  5. extractionThe aqueous mixture was extracted three times with EtOAc
  6. washThe EtOAc extracts were combined washed with saturated aqueous NaCl
  7. dry with materialdried over anhydrous Na2SO4
  8. customThe drying agent was removed by filtration
  9. customthe filtrate was evaporated at reduced pressure
  10. customaffording a pale yellow oil which
  11. distillationwas purified by chromatography and kugel rohr distillation

Sources & evidence

ORD record
ord-a913fa262eb34e938e1a350720b6e23a
Source dataset
uspto-grants-1991_01
Patent number
US04981863

Reaction notes

Loading…