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

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Reaction Steps

1-(4-Aminobutyl)-4-methoxybenzene hydrochloride (2.0 g, 9.27 mmol) was dissolved in water (10 ml). Toluene (20 ml) and 2N-sodium hydroxide (10 ml) were added and the mixture was partitioned. The organic layer was washed with 20% brine (10 ml) twice, dried over anhydrous sodium sulfate and concentrated under reduced pressure. To the residue was added methanol (5 ml) and the mixture was concentrated under reduced pressure. The residue was dissolved in methanol (10 ml). This methanol solution was added dropwise to a suspension of 2,2-dichloroacetaldehyde tosylhydrazone (5213 mg, 18.54 mmol) in methanol (30 ml) at 20-25° C. The mixture was stirred at room temperature for 1 hour 20 min. To the mixture of toluene (20 ml) and saturated aqueous sodium hydrogen carbonate (60 ml) was added this reaction mixture, and the mixture was stirred at room temperature for 50 min. The organic solvent was evaporated under reduced pressure and the residue was extracted with toluene (40 ml). 4N-Sodium hydroxide (30 ml) was added, and the mixture was heated to 50-60° C. and partitioned. Water (30 ml) was added, and the mixture was heated to 50-60° C. and partitioned. Water (30 ml) was added, and the mixture was heated to 50-60° C. and partitioned. The organic layer was washed with a mixture of 20% citric acid (15 ml) and saturated brine (15 ml). After washing with saturated aqueous sodium hydrogen carbonate (30 ml), it was washed with water (30 ml) and concentrated under reduced pressure. The residue was dissolved in ethyl acetate (10 ml) and methanesulfonic acid (0.49 ml, 7.55 mmol) was added under ice-cooling. Ethyl acetate (2 ml) was added and the mixture was stirred under ice-cooling for 50 min. The precipitated crystals were collected by filtration, washed with ice-cooled ethyl acetate (8 ml) and dried under reduced pressure to give 1-[4-(4-methoxyphenyl)butan-1-yl]-1H-1,2,3-triazole methanesulfonate (2.19 g, yield 72%).

Provenance & Evidence