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

HRID 257162Notes

Reaction equation

HRID 257162 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 Et0Ac 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-ce97e7cfceea460b86c31f1ce201a7bc
Source dataset
uspto-grants-1993_11
Patent number
US05260450

Reaction notes

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