Methyl iodide → HCID 59829798, compound

HRID 1947215Notes

Reaction equation

HRID 1947215 reaction equation
[CH:1]([N:4]1[C:8]([C:9]2[CH:14]=[C:13]([CH:15]([CH3:17])[CH3:16])[C:12]([O:18][CH2:19][O:20][CH3:21])=[CH:11][C:10]=2[O:22][CH2:23][O:24][CH3:25])=[N:7][NH:6][C:5]1=[S:26])([CH3:3])[CH3:2].[C:27](=O)([O-])[O-].[K+].[K+].CI>C(O)C>[CH:1]([N:4]1[C:5]([S:26][CH3:27])=[N:6][N:7]=[C:8]1[C:9]1[CH:14]=[C:13]([CH:15]([CH3:17])[CH3:16])[C:12]([O:18][CH2:19][O:20][CH3:21])=[CH:11][C:10]=1[O:22][CH2:23][O:24][CH3:25])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 59829899HCID 59829899, compound

Product 1

HCID 59829798HCID 59829798, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

4-isopropyl-5-(5-isopropyl-2,4-bis-methoxymethoxy-phenyl)-2,4-dihydro-[1,2,4]triazol-3-thione (F63-03, 1.96 g, 5.14 mmol) and potassium carbonate (710.4 mg, 5.14 mmol) were weighed and placed in a reaction vessel, and ethanol (30 mL) was added and then methyl iodide (0.32 mL, 5.14 mmol) was added. After heating at 80° C. for 1 hour while stirring, the mixture was returned to room temperature, and the solvent was distilled off under reduced pressure. After adding water, the reaction system was extracted with ethyl acetate, and the extract was washed with saturated sodium chloride solution. After drying the extract over anhydrous sodium, sodium sulfate was removed by filtration and the solvent was distilled off under reduced pressure to obtain yellow syrup. After purification by silica gel column chromatography (chloroform, methanol), 4-isopropyl-3-(5-isopropyl-2,4-bis-methoxy methoxyphenyl)-5-methylsulfanyl-4H-[1,2,4]triazole (F63-04, pale yellow syrup, 1.93 g, 95%) was obtained.

Workup

  1. customplaced in a reaction vessel
  2. customwas returned to room temperature
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionAfter adding water
  5. extractionthe reaction system was extracted with ethyl acetate
  6. washthe extract was washed with saturated sodium chloride solution
  7. customAfter drying the
  8. extractionextract over anhydrous sodium, sodium sulfate
  9. customwas removed by filtration
  10. distillationthe solvent was distilled off under reduced pressure
  11. customto obtain yellow syrup
  12. customAfter purification by silica gel column chromatography (chloroform, methanol)

Sources & evidence

ORD record
ord-1e91bab5109b44e286309b9267a32fdb
Source dataset
uspto-grants-2013_03
Patent number
US08399464B2

Reaction notes

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