Hydrochloric Acid → HCID 117988652, compound

Temperature

0 °C

7.1 ml of n-butyl lithium (1.6 M hexane solution) was added dropwise to a mixture of 1.62 g of 2,2,6,6-tetrahydropiperidine and 15 ml of THF at −78° C., and the mixture was heated to 0° C., then stirred at 0° C. for 10 minutes. 7 ml of a THF solution of 1.0 g of 6-trifluoromethylnicotinic acid was added to the reaction mixture at −78° C., and the mixture was stirred at −78° C. for 1 hour. Next, 1.42 ml of diethyl disulfide was added to the reaction mixture at −78° C., and heated to room temperature, then stirred at room temperature for 30 minutes. 10 ml of 1 N hydrochloric acid was poured to the reaction mixture, and the reaction mixture was separated into the organic layer and the aqueous layer. 1 N hydrochloric acid was added to the aqueous layer, and the precipitated solid was filtered. The resulting solid was washed with 1 N hydrochloric acid and n-hexane to obtain 0.52 g of 4-ethylsulfanyl-6-trifluoromethylnicotinic acid. The separated organic layer was allowed to stand overnight, and the precipitated solid was filtered, then washed with n-hexane to further obtain 0.68 g of 4-ethylsulfanyl-6-trifluoromethylnicotinic acid. 4-Ethylsulfanyl-6-trifluoromethylnicotinic acid

1. stirringthe mixture was stirred at −78° C. for 1 hour
2. temperatureheated to room temperature
3. stirringstirred at room temperature for 30 minutes
4. customthe reaction mixture was separated into the organic layer
5. addition1 N hydrochloric acid was added to the aqueous layer
6. filtrationthe precipitated solid was filtered
7. washThe resulting solid was washed with 1 N hydrochloric acid and n-hexane

ORD record

ord-1a490fd97fb240cd80896024f038144d

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09364000B2