Methyl iodide → 4H-1,2,4-Triazole, 4-methyl-3-(methylthio)-5-(2-naphthalenyl)-

HRID 1885276Notes

Reaction equation

HRID 1885276 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:8]=2)=[N:5][NH:4][C:3]1=[S:17].[C:18]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[CH3:1][N:2]1[C:3]([S:17][CH3:18])=[N:4][N:5]=[C:6]1[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 10243410HCID 10243410, compound

Product 1

HCID 30879994H-1,2,4-Triazole, 4-methyl-3-(methylthio)-5-(2-naphthalenyl)-

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2,4-dihydro-4-methyl-5-(2-naphthyl)-3H-1,2,4-triazole-3-thione (5.26 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 at reduced pressure and the concentrate was treated with water. The aqueous mixture was extracted with EtOAc three times. 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 to yield the desired product. Crystallization from EtOAc afforded colorless plates, Mp 177°-179° C.

Workup

  1. temperaturewarmed to reflux
  2. temperatureAfter refluxing overnight
  3. customthe solvent was evaporated at reduced pressure
  4. additionthe concentrate was treated with water
  5. extractionThe aqueous mixture was extracted with EtOAc three times
  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

Sources & evidence

ORD record
ord-d092d981565e49d0a8cb9756e1ae526b
Source dataset
uspto-grants-1992_09
Patent number
US05143933

Reaction notes

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