1,1-Dichloroethane → 2-Chloro-6-propylimidazo[1,2-b]pyridazine-3-sulfonamide

2-Chloro-6-n-propylimidazo[1,2-b]pyridazine (0.8 g, 4.1 mmol) and dichloroethane (10 ml) were introduced into a 200-ml eggplant type flask and stirred at room temperature, and chlorosulfonic acid (0.54 g, 4.5 mmol) was added thereto all at once, and the mixture was stirred for 4 hours under reflux. The reaction solution was cooled to about 70° C., and triethylamine (0.5 g, 5 mmol) was added thereto all at once and stirred until the solid was dissolved, and phosphorus oxychloride (0.79 g, 5 mmol) was added thereto all at once, and the mixture was stirred for 2 hours under reflux with heating. After the reaction was completed, the reaction solution was left and cooled, and water (50 ml) was added thereto and the organic phase was separated. The organic phase was washed with a saturated saline solution, dried over magnesium sulfate and concentrated, and acetonitrile (10 ml) and 28% ammonia water (4 ml) were added to the residue and stirred at room temperature for 2 hours. After the reaction was completed, water (100 ml) was added to the reaction solution which was then adjusted to about pH 2 with dilute hydrochloric acid, and the formed crystals were collected by filtration, washed with water and chloroform and dried under reduced pressure, to give the title compound as pale brown crystals. The yield was 0.49 g (43.5%; 3 steps).

1. stirringall at once, and the mixture was stirred for 4 hours
2. temperatureunder reflux
3. temperatureThe reaction solution was cooled to about 70° C.
4. stirringall at once and stirred until the solid
5. dissolutionwas dissolved
6. stirringall at once, and the mixture was stirred for 2 hours
7. temperatureunder reflux
8. temperaturewith heating
9. waitthe reaction solution was left
10. temperaturecooled
11. customthe organic phase was separated
12. washThe organic phase was washed with a saturated saline solution
13. dry with materialdried over magnesium sulfate
14. concentrationconcentrated
15. additionacetonitrile (10 ml) and 28% ammonia water (4 ml) were added to the residue
16. stirringstirred at room temperature for 2 hours
17. additionwater (100 ml) was added to the reaction solution which
18. filtrationthe formed crystals were collected by filtration
19. washwashed with water and chloroform
20. customdried under reduced pressure

ORD-Eintrag

ord-e746bf84e55844fa8eee03cdecda9702

Quelldatensatz

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08399381B2