Triethylamine → HCID 58610102, compound

Temperature

-15 °C

2-[(Cyclobutylcarbonyl)thio]benzoic acid (9.01 g, 38 mmol) was suspended in acetone (150 ml). While stirring under ice cooling, triethylamine (4.25 g, 42 mmol) and then ethyl chloroformate (4.88 g, 45 mmol) were dropwise added to the suspension. After stirring at the same temperature for an hour, an aqueous solution (15 ml) of sodium azide (2.92 g, 45 mmol) was dropwise added to the reaction mixture, followed by further stirring for an hour. The reaction mixture was diluted with water and the dilution was extracted with toluene. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and then filtered. The toluene solution was cooled to about −15° C. and a solution (15 ml) of tributylphosphine (7.70 g, 38 mmol) in toluene was dropwise added to the solution. After completion of the dropwise addition, the reaction temperature was reverted to room temperature and the mixture was heated under reflux for 10 minutes. The reaction solution was concentrated under reduced pressure. The residue was recrystallized from toluene-isopropyl ether to give the title compound (3.32 g, 40%) as crystals.

1. stirringAfter stirring at the same temperature for an hour
2. stirringby further stirring for an hour
3. extractionthe dilution was extracted with toluene
4. washThe extract was washed with saturated brine
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationfiltered
7. additionAfter completion of the dropwise addition
8. customwas reverted to room temperature
9. temperaturethe mixture was heated
10. temperatureunder reflux for 10 minutes
11. concentrationThe reaction solution was concentrated under reduced pressure
12. customThe residue was recrystallized from toluene-isopropyl ether

ORD record

ord-0db0e3c709354c2ab18c009147bcfb5a

Source dataset

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07659267B2