Hydrochloric Acid → HCID 20349369, compound

Temperature

60 °C

A solution was prepared by dissolving 19.63 grams (0.087 mole) of stannous chloride, dihydrate in 100 ml of acetone. To this mixture was added 7.3 ml of concentrated hydrochloric acid. The mixture was stirred for ~10 minutes. To this mixture was added a solution prepared by dissolving 12.8 grams (0.05 mole) of 2,6-dimethoxy-4-(trichloromethyl)pyridine in 40 ml of acetone at 30° C. The mixture was heated to reflux (60° C.) and refluxed for ~31/2 hours. The reaction mixture was cooled to ~15° C. and the acetone was removed at this temperature. The residual material was mixed with ~250 ml of water and raised to a pH of ~12 with ~20-30 ml of a 50 percent sodium hydroxide solution. The mixture was extracted twice with 250 ml portions of warm (60°-100° C.) petroleum ether and the petroleum ether extract washed twice with water. The petroleum ether extract was dried over sodium sulfate, filtered and the ether removed by evaporation. The desired 2,6-dimethoxy-4-(dichloromethyl)pyridine product was recovered from the residue by crystallization from hexane. The product melted at 59°-62° C. and was recovered in a yield of 7.3 grams (65.8 percent of theoretical). Upon analysis, the product was found to have carbon, hydrogen, nitrogen and chlorine contents of 43.44, 4.08, 6.32 and 31.68 percent, respectively, as compared to the theoretical contents of 43.26, 4.08, 6.30 and 31.93 percent, respectively, as calculated for the above-named compound. The structure of the compounds was confirmed by NMR.

1. customA solution was prepared
2. additionTo this mixture was added a solution
3. customprepared
4. temperatureThe mixture was heated
5. temperaturerefluxed for ~31/2 hours
6. temperatureThe reaction mixture was cooled to ~15° C.
7. customthe acetone was removed at this temperature
8. additionThe residual material was mixed with ~250 ml of water
9. temperatureraised to a pH of ~12 with ~20-30 ml of a 50 percent sodium hydroxide solution
10. extractionThe mixture was extracted twice with 250 ml portions
11. temperatureof warm (60°-100° C.) petroleum ether
12. extractionthe petroleum ether extract
13. washwashed twice with water
14. extractionThe petroleum ether extract
15. dry with materialwas dried over sodium sulfate
16. filtrationfiltered
17. customthe ether removed by evaporation
18. customThe desired 2,6-dimethoxy-4-(dichloromethyl)pyridine product was recovered from the residue by crystallization from hexane
19. customThe product melted at 59°-62° C. and was recovered in a yield of 7.3 grams (65.8 percent of theoretical)

ORD record

ord-be89f69da3994fbd9904277285b87611

Source dataset

uspto-grants-1980_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04190662