1,2-Dichloroethane → HCID 178455726, compound

To 20 g of 2,6-difluoro-4-(trans-4-vinylcyclohexyl) benzoic acid were then added 120 ml of 1,2-dichloroethane, 16 g of thionyl chloride and few drops of pyridine. The reaction mixture was then heated under reflux for 6 hours. The reaction mixture was then allowed to cool to room temperature. The solvents and excess thionyl chloride were distilled off under reduced pressure. To the residue was then added 150 ml of dichloromethane. The residue solution was then cooled to a temperature of 10° C. or lower. Ammonia was then introduced into the solution with stirring at a rate such that the liquid temperature was kept at 20° C. or lower. When heat generation was terminated, the solvents were then distilled off under reduced pressure. To the residue was then added 150 ml of N,N-dimethylformamide. The residue solution was then cooled to a temperature of 10° C. or lower. To the solution was then added dropwise 26.5 g of phosphorus oxychloride at a rate such that the liquid temperature was kept at 10° C. or lower. The temperature of the reaction solution was then returned to room temperature. The solution was then poured onto crushed ice. The resulting crystal was then filtered. The crystal thus obtained was washed with water, and then dried under reduced pressure. The crystal was then purified through silica gel column chromatography (solvent: toluene) to obtain 2,6-difluoro-4-(trans-4-vinylcyclohexyl)benzonitrile. The product was then recrystallized from ethanol to obtain 12.1 g of a purified product. The compound thus obtained had a melting point of 39° C.

1. temperatureThe reaction mixture was then heated
2. temperatureunder reflux for 6 hours
3. distillationThe solvents and excess thionyl chloride were distilled off under reduced pressure
4. additionTo the residue was then added 150 ml of dichloromethane
5. temperatureThe residue solution was then cooled to a temperature of 10° C.
6. additionAmmonia was then introduced into the solution
7. customwas kept at 20° C.
8. temperatureWhen heat generation
9. customwas terminated
10. distillationthe solvents were then distilled off under reduced pressure
11. additionTo the residue was then added 150 ml of N,N-dimethylformamide
12. temperatureThe residue solution was then cooled to a temperature of 10° C.
13. additionTo the solution was then added dropwise 26.5 g of phosphorus oxychloride at a rate such that the liquid temperature
14. customwas kept at 10° C.
15. customwas then returned to room temperature
16. additionThe solution was then poured
17. customonto crushed ice
18. filtrationThe resulting crystal was then filtered
19. customThe crystal thus obtained
20. washwas washed with water
21. customdried under reduced pressure
22. customThe crystal was then purified through silica gel column chromatography (solvent: toluene)

ORD record

ord-b98892ccd59745679bce717082523205

Source dataset

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06607791B1