反应详情

6-Fluoro-2(3H)-benzothiazolon-5-ylhydrazine (6.60 g) and 4-(2-hydroxyimino-1(6)-cyclohexen-1-yl)morpholine (6.50 g) were dissolved in ethanol (120 ml), a catalytic amount of acetic acid was added thereto, and the resulting mixture was heated under reflux for 5 hours. Water was added thereto, and the reaction mixture was extracted with ethyl acetate. The extract was concentrated, a mixture of cupric sulfate pentahydrate (16.0 g), water (64 g), 15% aqueous pyridine (160 g) and tetrahydrofuran (128 ml) was added thereto, and the resulting mixture was refluxed for 5 hours. After cooling, water and ethyl acetate were added thereto. The organic layer was separated from the aqueous layer, washed with dilute hydrochloric acid, dried and concentrated. The residue was purified by silica gel column chromatography using a mixture of ethyl acetate and hexane (1:9) as an eluent to give 2-[6-fluoro-2(3H)-benzothiazolon-5-yl]-4,5,6,7-tetrahydro-2H-benzotriazole-1-oxide (0.62 g).

1. temperaturethe resulting mixture was heated
2. temperatureunder reflux for 5 hours
3. extractionthe reaction mixture was extracted with ethyl acetate
4. concentrationThe extract was concentrated
5. additiona mixture of cupric sulfate pentahydrate (16.0 g), water (64 g), 15% aqueous pyridine (160 g) and tetrahydrofuran (128 ml)
6. additionwas added
7. temperaturethe resulting mixture was refluxed for 5 hours
8. temperatureAfter cooling
9. additionwater and ethyl acetate were added
10. customThe organic layer was separated from the aqueous layer
11. washwashed with dilute hydrochloric acid
12. customdried
13. concentrationconcentrated
14. customThe residue was purified by silica gel column chromatography
15. additiona mixture of ethyl acetate and hexane (1:9) as an eluent