Chlorobenzene → N-[3,5-Bis(trifluoromethyl)phenyl]-5-chloro-2-hydroxy-N-methylbenzamide

A mixture of 5-chlorosalicylic acid (173 mg, 1 mmol), 3,5-bis(trifluoromethyl)-N-methylaniline (243 mg, 1 mmol). phosphorus trichloride (44 μl, 0.5 mmol) and monochlorobenzene (5 mL) was refluxed for 3 hours under argon atmosphere. After the reaction mixture was cooled to room temperature, n-hexane (50 mL) was added, and the separated crude crystal was filtered and dissolved in ethyl acetate (50 mL). After the ethyl acetate solution was washed with water and brine one after another, dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=2:1) to give the title compound (75 mg, 13.9%) as a white crystal.

1. customthe separated crude crystal
2. filtrationwas filtered
3. dissolutiondissolved in ethyl acetate (50 mL)
4. washAfter the ethyl acetate solution was washed with water and brine one after another,
5. dry with materialdried over anhydrous sodium sulfate
6. customthe solvent was evaporated under reduced pressure
7. customThe obtained residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=2:1)

ORD record

ord-5c5e690c74954fa38b7ab31ff2910c4c

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08097759B2