Ethanol → HCID 20271288, compound

Crude sodium 2-(4-picolylthio)propionate (approximately 7 g.) was taken up in 100 ml. of absolute ethanol and approximately 5 cc. of 3 A molecular sieves were added. Dry hydrogen chloride was bubbled into the reaction mixture, which was refluxed for 75 minutes, while continuing to saturate with hydrogen chloride during the initial 15 minutes. The mixture was cooled to room temperature and allowed to stir overnight (approximately 16 hours). The mixture was filtered through diatomaceous earth and concentrated to a semi-solid mixture. The esterification step was repeated on this mixture, except saturation with hydrogen chloride was continued during 1 hour of reflux and refluxing was continued overnight. The reaction mixture was cooled to room temperature, filtered through diatomaceous earth and evaporated to an oil. The oil was extracted with chloroform, leaving filterable salts behind, and the chloroform stripped to yield ethyl 2-(4-picolylthio)propionate (waxy solid; ir (KBr) 3.0, 3.5, 5.75, 6.15, 6.30, 6.70, 8.6, 12.25μ; m.s.: m/e calcd: 225; found: 225, 152, 124, 102, 92, 45).

1. additionof 3 A molecular sieves were added
2. customDry hydrogen chloride was bubbled into the reaction mixture, which
3. temperaturewas refluxed for 75 minutes
4. concentrationto saturate with hydrogen chloride during the initial 15 minutes
5. filtrationThe mixture was filtered through diatomaceous earth
6. concentrationconcentrated to a semi-solid mixture
7. waitwas continued during 1 hour
8. temperatureof reflux
9. temperaturerefluxing
10. waitwas continued overnight
11. temperatureThe reaction mixture was cooled to room temperature
12. filtrationfiltered through diatomaceous earth
13. customevaporated to an oil
14. extractionThe oil was extracted with chloroform
15. customleaving filterable salts behind, and the chloroform

ORD record

ord-78dc2c67ab7041e5b5f517f76e76cf37

Source dataset

uspto-grants-1983_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04371696