Benzene → HCID 18957822, compound

A solution of 0.26 g of 4-trifluoromethyl-3-pyridine carboxylic acid and 0.24 g of thionyl chloride in 10 ml of benzene was refluxed under heating for 30 minutes in the presence of a catalytic amount of dimethylformamide. Excess thionyl chloride and benzene were distilled off under reduced pressure. Then, the residue was dissolved in 15 ml of tetrahydrofuran. Then, 0.21 g of triethylamine and 0.12 g of allylamine were added thereto, and the mixture was stirred at room temperature for 20 hours. Then, the mixture was poured into an aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 0.21 g of the desired product (Compound No. 22) having a melting point of from 75.5° to 77° C.

1. distillationExcess thionyl chloride and benzene were distilled off under reduced pressure
2. dissolutionThen, the residue was dissolved in 15 ml of tetrahydrofuran
3. additionThen, 0.21 g of triethylamine and 0.12 g of allylamine were added
4. additionThen, the mixture was poured into an aqueous ammonium chloride solution
5. extractionextracted with ethyl acetate
6. washThe organic layer was washed with water
7. dry with materiala saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by silica gel column chromatography

ORD record

ord-ab32af71dcc046ebaa464d9f154c821b

Source dataset

uspto-grants-1994_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05360806