Water → 1,5-bis(4-methoxyphenyl)-3-(methylthio)-1H-1,2,4-triazole

HRID 584733Notes

Reaction equation

HRID 584733 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)=[N:12][C:11]([SH:22])=[N:10]2)=[CH:5][CH:4]=1.IC.Cl[CH2:26]Cl.O>[OH-].[Na+]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[C:13]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)=[N:12][C:11]([S:22][CH3:26])=[N:10]2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 6344DichloromethaneHCID 178489023HCID 178489023, compound

Product 1

HCID 99234391,5-bis(4-methoxyphenyl)-3-(methylthio)-1H-1,2,4-triazoleYield 47.9%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To a mixture of 1,5-bis(4-methoxyphenyl)-1H-1,2,4-triazole-3-thiol (470 mg, 1.5 mmol) in 1N sodium hydroxide solution (5 mL), was added iodomethane (0.934 mL, 15 mmol). The mixture was shaken overnight. Dichloromethane and water were added to the mixture and the organic layer was separated, washed with 0.1 N hydrochloric acid and sat sodium bicarbonate, and brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure.The generated precipitate was isolated by filtration, washed with diisopropyl ether, and dried in vacuo to give 1,5-bis(4-methoxyphenyl)-3-(methylthio)-1H-1,2,4-triazole (235 mg, 47.9% yield).

Workup

  1. customthe organic layer was separated
  2. washwashed with 0.1 N hydrochloric acid
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customThe generated precipitate was isolated by filtration
  6. washwashed with diisopropyl ether
  7. customdried in vacuo

Sources & evidence

ORD record
ord-f41dbe4842ff4a748485eb4f21c9d6b5
Source dataset
uspto-grants-2005_08
Patent number
US06927230B2

Reaction notes

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