Sodium hydride → HCID 66834104, Verbindung

To a mixture of 3-amino-4-bromo-benzonitrile (1.98 g, 10 mmol), TEA (5.06 g, 50 mmol), and methylene chloride (50 ml), mesyl chloride (2.71 ml, 35 mmol) was added at 0° C. and the mixture was stirred at room temperature for 30 min. Water was added to the reaction solution, which was then extracted with dichloromethane. The organic layer was dried over sodium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were added with tetrahydrofuran (100 ml), water (400 μl) and sodium hydride (540 mg, 15.5 mmol), and stirred at room temperature for 16 hr. To the reaction solution, saturated aqueous solution of ammonium chloride (200 ml) was added followed by extraction with ethyl acetate. The organic layer was dried over sodium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (2.48 g, 90%).

1. additionwas added at 0° C.
2. extractionwas then extracted with dichloromethane
3. dry with materialThe organic layer was dried over sodium sulfate
4. customThe drying agent was removed by filtration
5. customthe residues obtained
6. concentrationafter concentration under reduced pressure
7. stirringstirred at room temperature for 16 hr
8. extractionfollowed by extraction with ethyl acetate
9. dry with materialThe organic layer was dried over sodium sulfate
10. customThe drying agent was removed by filtration
11. customthe residues obtained
12. concentrationafter concentration under reduced pressure
13. customwere purified by silica gel column chromatography (hexane/ethyl acetate)

ORD-Eintrag

ord-99f6e00c20614ebc994b3c5e945c3b50

Quelldatensatz

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09126931B2