Acetic Acid → 2-(Trichloromethyl)oxazolidine

To a 2 liter 3-necked flask equipped with a stirrer, Dean-Stark trap, a condenser and dropping funnel were added 214 g (3.51 moles) ethanolamine and 450 g. toluene. Then 273 g (4.55 moles) of glacial acetic acid were added slowly to keep the temperature (cooling if necessary) at 30°-45° C. Then 568 g (3.85 moles) of chloral were added at 40°-50° C. The reaction mixture was refluxed to remove water and, when complete, the temperature increased to 115°-120° C. The reaction mixture was cooled in an ice bath and the product precipitated after standing for several hours to give 189.5 g (28.5%) m.p. 72°-74° C. The filtrate was washed with 5.0 moles of 20% sodium hydroxide and more product precipitated. Filtration and drying yielded 228.5 g (34.3%), m.p. 73°-75° C. The toluene layer was washed with water and evaporated to give a solid. Washing with water and filtration yielded upon drying 328 g. (49.2%), m.p. 62°-72° C. for a total yield of 556.0 g (83.5%). The analysis was consistent with the assigned structure.

1. customTo a 2 liter 3-necked flask equipped with a stirrer
2. temperaturethe temperature (cooling if necessary) at 30°-45° C
3. temperatureThe reaction mixture was refluxed
4. customto remove water and, when complete
5. temperaturethe temperature increased to 115°-120° C
6. temperatureThe reaction mixture was cooled in an ice bath
7. customthe product precipitated
8. waitafter standing for several hours
9. customto give 189.5 g (28.5%) m.p. 72°-74° C
10. customprecipitated
11. filtrationFiltration
12. customdrying
13. customyielded 228.5 g (34.3%), m.p. 73°-75° C
14. washThe toluene layer was washed with water
15. customevaporated
16. customto give a solid
17. washWashing with water and filtration
18. customyielded
19. customupon drying 328 g

ORD-Eintrag

ord-dc2019b6a5c54e4db5f086b11d45ad18

Quelldatensatz

uspto-grants-1980_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04226948