Sodium Azide → HCID 14227209, compound

To a stirred solution of sodium azide (1.32 g) in water (5 ml) at 0° C. was added a solution of 10-undecenoyl chloride (4.30 ml) in dioxane (10 ml). The mixture was stirred for 45 minutes, and poured into ice water (100 ml). The mixture was extracted twice with benzene (50 ml), and the combined extracts were washed with ice water (25 ml), dried (MgSO4), and filtered. The filtrate was heated to reflux under a Dean-Stark trap, removing the first 30 ml of distillate. After 30 minutes at reflux, the reaction was cooled and evaporated, to provide 9-decenyl icocyanate as a colorless oil. This isocyanate was dissolved in DMF (5 ml) and added to a slurry of N-methylhydroxylamine hydrochloride (1.70 g) and triethylamine (2.84 ml) in DMF (20 ml). After two hours, the reaction mixture was filtered through Celite and quenched with water. The resulting solids were collected by filtration, washed with water, and recrystallized from ethyl acetate to provide the title compound as a white solid (1.35 g), mp 58°-59° C.

1. extractionThe mixture was extracted twice with benzene (50 ml)
2. washthe combined extracts were washed with ice water (25 ml)
3. dry with materialdried (MgSO4)
4. filtrationfiltered
5. temperatureThe filtrate was heated
6. temperatureto reflux under a Dean-Stark trap
7. customremoving the first 30 ml of distillate
8. temperatureAfter 30 minutes at reflux
9. temperaturethe reaction was cooled
10. customevaporated
11. customto provide 9-decenyl icocyanate as a colorless oil
12. waitAfter two hours
13. filtrationthe reaction mixture was filtered through Celite
14. customquenched with water
15. filtrationThe resulting solids were collected by filtration
16. washwashed with water
17. customrecrystallized from ethyl acetate

ORD record

ord-e2fd5b7e2ee24bbea6d5759c350b18b6

Source dataset

uspto-grants-1991_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05066658