Sulfuric Acid → HCID 11206127, compound

To a solution of 8.25 g (0.15 mole) propionitrile in 25 mL glacial acetic acid, 15 g concentrated sulfuric acid was added dropwise while controlling the reaction temperature at about 38° C., then 5.2 g (0.051 mole) of 2,3-dimethyl-2-butanol was added dropwise at the temperature below 40° C. with stirring. The mixture was stirred overnight while maintaining the temperature, then poured into glacial water, basified with 40% sodium hydroxide solution and extracted with ether. The ether extract was combined, washed once with water, and dried over anhydrous magnesium sulfate. After recovering the ether, 6.2 g light yellow liquid was obtained and solved in 80 mL anhydrous ether. The resulting solution was added dropwise to a suspension of 3.04 g (0.08 mol) lithium aluminium hydride in 80 mL anhydrous ether. The mixture was refluxed for 10 hours, then cooled. To the mixture, proper amount of 40% aqueous sodium hydroxide was added dropwise and the upper layer of ether was carefully poured out. The lower layer of solid was then washed with ether (×3). The resulting washing and extract ether were combined, dried over anhydrous potassium carbonate and filtered. To the filtrate, HCl-Et2O was added under cooling until the solution is acidic. The solid was collected by filtering and recrystallized three times from iso-propanol and acetone to give a white lamellar crystal 3.33 g (yield 46.33%), mp 183-185° C. Elemental analysis for C9H22NCI (%): Calculated C, 10.15; H, 12.34; N, 7.79. Found C, 60.20; H, 13.80; N, 7.85. 1H-NMR(D2O, ppm) 0.98(d, 6H), 1.00(t, 3H), 1.24(s, 6H), 1.63(m, 2H), 2.05(m, 1H), 2.98(t, 2H). MS(m/z) 143(M+).

1. customat about 38° C.
2. stirringThe mixture was stirred overnight
3. temperaturewhile maintaining the temperature
4. extractionextracted with ether
5. extractionThe ether extract
6. washwashed once with water
7. dry with materialdried over anhydrous magnesium sulfate
8. customAfter recovering the ether, 6.2 g light yellow liquid
9. customwas obtained
10. temperatureThe mixture was refluxed for 10 hours
11. temperaturecooled
12. washThe lower layer of solid was then washed with ether (×3)
13. washThe resulting washing
14. extractionextract ether
15. dry with materialdried over anhydrous potassium carbonate
16. filtrationfiltered
17. additionTo the filtrate, HCl-Et2O was added
18. temperatureunder cooling until the solution
19. customThe solid was collected
20. filtrationby filtering
21. customrecrystallized three times from iso-propanol and acetone

ORD record

ord-de6e1a1c29cb4f70937e019ba367222d

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07560473B2