Ammonia → 3-Chloro-2-fluoro-6-(trifluoromethyl)benzamide

Temperature

5 °C

420 g of thionyl chloride was added to 286 g of 3-chloro-2-fluoro-6-trifluoromethylbenzoic acid, and to the resultant mixture was further added 5 drops of triethylamine and the mixture then heated at reflux for 4 hours. After cooling, the reaction mixture was concentrated under reduced pressure, and 3-chloro-2-fluoro-6-trifluoromethylbenzoyl chloride obtained was added into 1 liter of 28% aqueous ammonia solution, which has be cooled down to 5° C. over 10 minutes with stirring. Then. the solution was further stirred for 1 hour at room temperature. The reaction mixture was extracted with ether, and the extract was washed with water and with saturated saline solution and dried over anhydrous magnesium sulfate. The solvent was distilled under reduced pressure, and the crude crystals obtained were washed with n-hexane and then filtered to obtain 266 g of the title compound(mp. 123-125° C.).

1. temperaturethe mixture then heated
2. temperatureat reflux for 4 hours
3. temperatureAfter cooling
4. concentrationthe reaction mixture was concentrated under reduced pressure, and 3-chloro-2-fluoro-6-trifluoromethylbenzoyl chloride
5. customobtained
6. stirringthe solution was further stirred for 1 hour at room temperature
7. extractionThe reaction mixture was extracted with ether
8. washthe extract was washed with water and with saturated saline solution
9. dry with materialdried over anhydrous magnesium sulfate
10. distillationThe solvent was distilled under reduced pressure
11. customthe crude crystals obtained
12. washwere washed with n-hexane
13. filtrationfiltered

ORD record

ord-4f99a5cb35c4426585220401fc5fd1a2

Source dataset

uspto-grants-2000_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06054605