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

HRID 257161Notes

Reaction equation

HRID 257161 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-triazole

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: 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. washwashed 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
  12. customaffording a pale yellow oil

Sources & evidence

ORD record
ord-10fd91cbb0b644b8a551b2c5bd34dcdb
Source dataset
uspto-grants-1993_11
Patent number
US05260450

Reaction notes

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