Ammonia → 2,3-Dichloro-6-(trifluoromethyl)benzamide

Temperature

5 °C

To a solution of 250 g of 2,3-dichloro-6-trifluoromethylbenzoic acid in 2 liters of benzene was added 5 drops of pyridine and 172 g of thionyl chloride and then the mixture was heated at reflux for 22 hours. After cooling down, the solution was concentrated under reduced pressure, and 2,3-dichloro-6-trifluoromethylbenzyl chloride obtained was added into 1 liter of 28% aqueous ammonia solution, which has been 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 ethyl acetate, and the extract was washed with water and then with saturated saline solution, and was 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 give 229 g of the title compound(mp. 118-20° C.).

1. temperaturethe mixture was heated
2. temperatureat reflux for 22 hours
3. temperatureAfter cooling down
4. concentrationthe solution was concentrated under reduced pressure, and 2,3-dichloro-6-trifluoromethylbenzyl chloride
5. customobtained
6. stirringThen, the solution was further stirred for 1 hour at room temperature
7. extractionThe reaction mixture was extracted with ethyl acetate
8. washthe extract was washed with water
9. dry with materialwith saturated saline solution, and was dried 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-95de71d43eb2490e873cae9b9aeed6fb

Source dataset

uspto-grants-2000_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06054605