Hydrochloric Acid → HCID 15186745, compound

Temperature

0 °C

3,5-Difluoroaniline (64.5 g, 0.5 mol) is added to a solution of water (206 ml) and concentrated hydrochloric acid (116 ml). The resulting solution is stirred for 10 minutes and cooled to 0° C. A solution of sodium nitrate (37.4 g, 0.54 mol) in water (125 ml) is added in a dropwise manner. After being stirred for one hour, the mixture is filtered and the filtrate is cooled to 0° C. A solution of sodium azide (40.2 g, 0.62 mol) in water (125 ml) is added in a dropwise manner, and stirring is allowed to continue for 30 minutes. The reaction mixture is extracted with ether (3×250 ml), and the combined organic extracts are washed with saturated sodium bicarbonate solution (250 ml) and then brine (250 ml), and dried over sodium sulfate. Removal of the volatiles in vacuo affords pure title compound as a yellow liquid (70 g, 90%).

1. stirringAfter being stirred for one hour
2. filtrationthe mixture is filtered
3. temperaturethe filtrate is cooled to 0° C
4. stirringstirring
5. waitto continue for 30 minutes
6. extractionThe reaction mixture is extracted with ether (3×250 ml)
7. washthe combined organic extracts are washed with saturated sodium bicarbonate solution (250 ml)
8. dry with materialbrine (250 ml), and dried over sodium sulfate
9. customRemoval of the volatiles in vacuo

ORD record

ord-0e4ebfb1543c4b1491dc063b6f4a9511

Source dataset

uspto-grants-2003_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06642390B2