Dimethyl Sulfoxide → HCID 13560201, compound

Temperature

20 °C

In a reaction flask with condenser, mechanical stirrer, thermometer and dropping funnel were placed 53.4 g of 3,6-dichloro-2-pyridinecarbonitrile and 300 ml of DMSO. The mixture was chilled to about 10°-15° C. and then 19.8 g of ethanethiol was added. While maintaining the temperature at <20° C., 34.8 g of t-BuOK in 300 ml of THF was added in small portions. After the addition was complete, the reaction mixture was warmed to 20° C. and stirred for about 40 hrs. The reaction mixture was then poured onto about 2 kilograms (kg) of ice, stirred and filtered leaving a solid residue. The residue was washed with water, dissolved in CH2Cl2, dried over MgSO4, concentrated and diluted with hexane to give 19.0 g of 6-chloro-3-ethylthio-2-pyridinecarbonitrile. The filtrate was concentrated and separated on a Water's Prep LC 500 instrument using 15% ethyl acetate in hexane to give another 10.1 g of the same isomer. Total yield of 6-chloro-3-ethylthio-2-pyridinecarbonitrile was 29.1 g (46.5%), m.p. 79°-81° C. Further separation on the Prep LC 500 instrument gave a small amount of 3-chloro-6-ethylthio-2-pyridinecarbonitrile (m.p. 46°-48° C.) and 3,6-bis-ethylthio-2-pyridinecarbonitrile (m.p. 63°-64° C.).

1. customIn a reaction flask with condenser, mechanical stirrer, thermometer and dropping
2. customfunnel were placed
3. temperatureThe mixture was chilled to about 10°-15° C.
4. temperatureWhile maintaining the temperature at <20° C.
5. additionAfter the addition
6. stirringstirred
7. filtrationfiltered
8. customleaving a solid residue
9. washThe residue was washed with water
10. dissolutiondissolved in CH2Cl2
11. dry with materialdried over MgSO4
12. concentrationconcentrated
13. additiondiluted with hexane

ORD record

ord-cb961e4dc3534e3ea50237c50247d6db

Source dataset

uspto-grants-1985_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04558134