Ammonium Chloride → 2,3-Butanediamine, N,N'-dihydroxy-2,3-dimethyl-

Temperature

9 °C

2,3-Dimethyl-2,3-dinitrobutane (82.56 g, 0.47 mmol) was dissolved in a mixture of THF (1407 mL) and water (235 mL). To this solution cooled to 8-10° C., Zn powder (126.9 g, 1.95 mol) was added in one portion. A solution of NH4Cl (202.1 g, 3.77 mol) in H2O (705 mL) was added dropwise to this slurry, with continued stirring for 1 h at 10° C., and the flask was stored in cooled water for 16 h. The slurry was filtered, and the precipitate was carefully washed with THF (4×200 mL). The precipitate was then dried by three washings with diethyl ether and collected. The solution was evaporated under vacuum until THF ceased to distill off. Then the solution was protected from air, and sodium carbonate (235 g) and sodium chloride (141 g) were added with cooling. Continuous extraction with chloroform (1880 mL) was performed over 18 h. The filtrate was concentrated to give oil product, then added petroleum ether to this mixture and stirred for 30 min at room temperature, filtered, dried, to afford a white powder (12.8 g, 18.4% yield). 1HNMR (400 MHz, DMSO): δ 6.89 (s, 1 H), 5.34 (s, 1 H), 0.96 (s, 3 H).

1. filtrationThe slurry was filtered
2. washthe precipitate was carefully washed with THF (4×200 mL)
3. dry with materialThe precipitate was then dried by three washings with diethyl ether
4. customcollected
5. customThe solution was evaporated under vacuum until THF
6. distillationto distill off
7. additionwere added
8. temperaturewith cooling
9. extractionContinuous extraction with chloroform (1880 mL)
10. waitwas performed over 18 h
11. concentrationThe filtrate was concentrated
12. customto give oil product
13. filtrationfiltered
14. customdried

ORD record

ord-de6647ee79c84e09bf334d79ddadefa1

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08377670B2