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

HRID 352049Notes

Reaction equation

HRID 352049 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.[NH:14]1[CH:18]=[CH:17][N:16]=[N:15]1.[I-].[K+].[OH-].[Na+].[CH3:23][S:24]([OH:27])(=[O:26])=[O:25].C(OCC)(=O)C.C(OC(C)C)(C)C>O.C1(C)C=CC=CC=1.C(O)(C)(C)C>[CH3:23][S:24]([OH:27])(=[O:26])=[O:25].[CH3:13][O:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][CH2:3][CH2:2][N:14]2[CH:18]=[CH:17][N:16]=[N:15]2)=[CH:7][CH:8]=1

Participants

10

Reactant 6

HCID 4875Potassium IodideHCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 2848821-(4-Chlorobutyl)-4-methoxybenzeneHCID 22281796Diisopropylether ethyl acetateHCID 178418936HCID 178418936, compound

Product 1

HCID 865876341-[4-(4-methoxyphenyl)butan-1-yl]-1H-1,2,3-triazole methanesulfonateYield 83.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6386tert-ButanolSolvent

Procedure

1-(4-Chlorobutyl)-4-methoxybenzene (950 mg, 4.78 mmol), 1H-1,2,3-triazole (660 mg, 9.55 mmol) and potassium iodide (793 mg, 4.78 mmol) were added to t-butanol (5 ml). Sodium hydroxide (382 mg, 9.55 mmol) was added and the mixture was refluxed under heating for 11 hours. After cooling to room temperature, toluene and water were added and the mixture was partitioned. The organic layer was washed successively with water, 20% citric acid, saturated aqueous sodium hydrogen carbonate and water, and was concentrated under reduced pressure. To the residue were added ethyl acetate (6 ml) and isopropyl ether (3 ml). Methanesulfonic acid (402 mg, 4.18 mmol) was added at room temperature. Ethyl acetate/isopropyl ether=2/1 (2 ml) was added and the mixture was stirred at room temperature for 30 min. The precipitated crystals were collected by filtration and dried under reduced pressure to give 1-[4-(4-methoxyphenyl)-butan-1-yl]-1H-1,2,3-triazole methanesulfonate (1.14 g, yield 73%).

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 11 hours
  3. customthe mixture was partitioned
  4. washThe organic layer was washed successively with water, 20% citric acid, saturated aqueous sodium hydrogen carbonate and water
  5. concentrationwas concentrated under reduced pressure
  6. additionTo the residue were added ethyl acetate (6 ml) and isopropyl ether (3 ml)
  7. filtrationThe precipitated crystals were collected by filtration
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-0b38f57804404c50aa02a223aa8462b5
Source dataset
uspto-grants-2004_06
Patent number
US06743924B2

Reaction notes

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