Methyl iodide → HCID 59829879, compound

HRID 1947199Notes

Reaction equation

HRID 1947199 reaction equation
[CH:1]([C:4]1[C:5]([O:33][CH2:34][O:35][CH3:36])=[CH:6][C:7]([O:29][CH2:30][O:31][CH3:32])=[C:8]([C:10]2[N:11]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[CH:18][CH:17]=3)[C:12](=[S:15])[NH:13][N:14]=2)[CH:9]=1)([CH3:3])[CH3:2].[C:37](=O)([O-])[O-].[K+].[K+].CI>C(O)C>[CH:1]([C:4]1[C:5]([O:33][CH2:34][O:35][CH3:36])=[CH:6][C:7]([O:29][CH2:30][O:31][CH3:32])=[C:8]([C:10]2[N:11]([C:16]3[CH:17]=[CH:18][C:19]([CH2:22][N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[CH:20][CH:21]=3)[C:12]([S:15][CH3:37])=[N:13][N:14]=2)[CH:9]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 59829782HCID 59829782, compound

Product 1

HCID 59829879HCID 59829879, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

5-(5-isopropyl-2,4-bis-methoxymethoxyphenyl)-4-(4-molpholin-4-ylmethylphenyl)-2,4-dihydro-[1,2,4]triazol-3-thione (F45-03, 2.43 g, 4.72 mmol) and potassium carbonate (653 mg, 4.72 mmol) were weighed and placed in a reaction vessel, and ethanol (30 mL) and then methyl iodide (0.29 mL, 4.72 mmol) were added. After heating at 80° C. stirring for an hour, the reaction mixture was returned to room temperature, and the solvent was distilled off under reduced pressure. The reaction system was mixed with water, extracted with ethyl acetate, and the extract was washed with saturated sodium chloride solution. After drying the extract over anhydrous sodium sulfate, sodium sulfate was removed by filtration and the solvent was distilled off under reduced pressure to obtain a pale yellow foam (2.18 g) containing 3-(5-isopropyl-2,4-bis-methoxymethoxyphenyl)-4-(4-molpholin-4-ylmethylphenyl)-5-methylsulfanyl-4H-[1,2,4]triazole (F45-04).

Workup

  1. customplaced in a reaction vessel
  2. customwas returned to room temperature
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionThe reaction system was mixed with water
  5. extractionextracted with ethyl acetate
  6. washthe extract was washed with saturated sodium chloride solution
  7. customAfter drying the
  8. extractionextract over anhydrous sodium sulfate, sodium sulfate
  9. customwas removed by filtration
  10. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-eeb0da59b15b43e896a81e82840b9988
Source dataset
uspto-grants-2013_03
Patent number
US08399464B2

Reaction notes

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