反应详情

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%).

1. customthe mixture was partitioned
2. washThe organic layer was washed with 20% brine (10 ml) twice
3. dry with materialdried over anhydrous sodium sulfate
4. concentrationconcentrated under reduced pressure
5. additionTo the residue was added methanol (5 ml)
6. concentrationthe mixture was concentrated under reduced pressure
7. dissolutionThe residue was dissolved in methanol (10 ml)
8. additionwas added this reaction mixture
9. stirringthe mixture was stirred at room temperature for 50 min
10. customThe organic solvent was evaporated under reduced pressure
11. extractionthe residue was extracted with toluene (40 ml)
12. addition4N-Sodium hydroxide (30 ml) was added
13. temperaturethe mixture was heated to 50-60° C.
14. custompartitioned
15. additionWater (30 ml) was added
16. temperaturethe mixture was heated to 50-60° C.
17. custompartitioned
18. additionWater (30 ml) was added
19. temperaturethe mixture was heated to 50-60° C.
20. custompartitioned
21. washThe organic layer was washed with a mixture of 20% citric acid (15 ml) and saturated brine (15 ml)
22. washAfter washing with saturated aqueous sodium hydrogen carbonate (30 ml), it
23. washwas washed with water (30 ml)
24. concentrationconcentrated under reduced pressure
25. dissolutionThe residue was dissolved in ethyl acetate (10 ml)
26. temperaturecooling
27. stirringthe mixture was stirred under ice-
28. temperaturecooling for 50 min
29. filtrationThe precipitated crystals were collected by filtration
30. washwashed with ice-
31. temperaturecooled ethyl acetate (8 ml)
32. customdried under reduced pressure