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

1-(4-Aminobutyl)-4-methoxybenzene hydrochloride (1.0 g, 4.64 mmol) was dissolved in water. Toluene (10 ml) and 2N-sodium hydroxide (10 ml) were added and the mixture was partitioned. The organic layer was washed with 20% brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was dissolved in methanol (8 ml), and a suspension of 2,2-dichloroacetaldehyde tosylhydrazone (2.61 g, 9.28 mmol) in methanol (12 ml) was added dropwise at 15-20° C. The mixture was stirred at room temperature for 2 hours and concentrated under reduced pressure. To the residue was added ethyl acetate (50 ml) and then was added saturated aqueous sodium hydrogen carbonate (50 ml). The mixture was stirred for 10 min and partitioned, which was followed by washing with saturated brine and concentration under reduced pressure. Purification by silica gel column gave 1-[4-(4-methoxyphenyl)butan-1-yl]-1H-1,2,3-triazole (1.1 g, yield 100%).

1. customthe mixture was partitioned
2. washThe organic layer was washed with 20% brine
3. dry with materialdried over anhydrous sodium sulfate
4. concentrationconcentrated under reduced pressure
5. dissolutionThe residue was dissolved in methanol (8 ml)
6. additionwas added dropwise at 15-20° C
7. concentrationconcentrated under reduced pressure
8. additionTo the residue was added ethyl acetate (50 ml)
9. additionwas added saturated aqueous sodium hydrogen carbonate (50 ml)
10. stirringThe mixture was stirred for 10 min
11. custompartitioned
12. washby washing with saturated brine and concentration under reduced pressure
13. customPurification by silica gel column

ORD record

ord-f4752b3914594959bd5c7f1a810e077e

Source dataset

uspto-grants-2004_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06743924B2