Potassium Iodide → 1-[4-(4-methoxyphenyl)butan-1-yl]-1H-1,2,3-triazole methanesulfonate

HRID 352050Notes

Reaction equation

HRID 352050 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1.CC(O)(CC)C.[NH:20]1[CH:24]=[CH:23][N:22]=[N:21]1.[I-].[K+].[OH-].[Na+].[CH3:29][S:30]([OH:33])(=[O:32])=[O:31]>O.C1(C)C=CC=CC=1>[CH3:29][S:30]([OH:33])(=[O:32])=[O:31].[CH3:13][O:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][CH2:3][CH2:2][N:20]2[CH:24]=[CH:23][N:22]=[N:21]2)=[CH:7][CH:8]=1

Participants

9

Reactant 6

HCID 4875Potassium IodideHCID 6395Methanesulfonic AcidHCID 64052-Methyl-2-butanolHCID 14798Sodium HydroxideHCID 2848821-(4-Chlorobutyl)-4-methoxybenzeneHCID 178418936HCID 178418936, compound

Product 1

HCID 865876341-[4-(4-methoxyphenyl)butan-1-yl]-1H-1,2,3-triazole methanesulfonateYield 87.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To 1-(4-Chlorobutyl)-4-methoxybenzene (2468 mg, 12.42 mmol) was added 2-methyl-2-butanol (5 ml), and then 1H-1,2,3-triazole (1286 mg, 18.62 mmol) and potassium iodide (2062 mg, 14.24 mmol) were added. Sodium hydroxide (745 mg, 18.62 mmol) was added and the mixture was refluxed under heating for 4 hours. After cooling to room temperature, toluene and water were added and the mixture was partitioned. The organic layer was washed with water, 20%citric acid (twice), saturated aqueous sodium hydrogen carbonate and water (twice). The organic layer was concentrated under reduced pressure. To the residue was added ethyl acetate and the mixture was concentrated under reduced pressure. Ethyl acetate (20 ml) and isopropyl ether (10 ml) were added and then seed crystal was added. Methanesulfonic acid (1021 mg, 10.62 mmol) was added dropwise while keeping the mixture at 20-30° C. The mixture was stirred at 20-30° C. for 1 hour. The precipitated crystals were collected by filtration and washed with ethyl acetate/isopropyl ether=1/1. The crystals were dried under reduced pressure to give 1-[4-(4-methoxyphenyl)butan-1-yl]-1H-1,2,3-triazole methanesulfonate (3.04 g) as white crystals (yield 75%).

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 4 hours
  3. customthe mixture was partitioned
  4. washThe organic layer was washed with water, 20%citric acid (twice), saturated aqueous sodium hydrogen carbonate and water (twice)
  5. concentrationThe organic layer was concentrated under reduced pressure
  6. additionTo the residue was added ethyl acetate
  7. concentrationthe mixture was concentrated under reduced pressure
  8. additionEthyl acetate (20 ml) and isopropyl ether (10 ml) were added
  9. additionseed crystal was added
  10. customat 20-30° C
  11. filtrationThe precipitated crystals were collected by filtration
  12. washwashed with ethyl acetate/isopropyl ether=1/1
  13. customThe crystals were dried under reduced pressure

Sources & evidence

ORD record
ord-62b4a2b7e12d49d98d141202d8b1832b
Source dataset
uspto-grants-2004_06
Patent number
US06743924B2

Reaction notes

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