Hydrochloric Acid → Octyl Maleimide

Temperature

30 °C

To a suspension of maleic anhydride (54, 5.4 g, 55 mmol) in 150 ml of benzene, a solution of octyl amine (53, 6.46 g, 50 mmol) in 100 ml of benzene was added. The resulting mixture was stirred at 30° C. for an hour and ZnBr2 (12.4 g, 55 mmol) and hexamethyl disilazane (12.1 g, 75 mmol) in 30 ml of benzene were added. The resulting suspension was refluxed for 2 hrs. After cooling to room temperature, the reaction mixture was poured into 200 ml of 0.5 M HCl. The organic layer was separated and the aqueous portion was extracted twice with 150 ml portions of EtOAc. The combined organic layers were washed with saturated aqueous NaHCO3 (2×150 ml), brine (1×150 ml), and dried over Na2SO4. The solution was dried under vacuum to yield an oily product which solidified gradually to yield the cream colored solid product (9.2 g, 88%). 1H NMR (300 MHz, CDCl3): δ 0.87 (t, 3H, J=6 Hz), 1.20-1.40 (m, 10H), 1.50-1.70 (m, 2H), 3.51 (t, 2H, J=6 Hz), 6.69 (s, 2H).

1. temperatureThe resulting suspension was refluxed for 2 hrs
2. temperatureAfter cooling to room temperature
3. customThe organic layer was separated
4. extractionthe aqueous portion was extracted twice with 150 ml portions of EtOAc
5. washThe combined organic layers were washed with saturated aqueous NaHCO3 (2×150 ml), brine (1×150 ml)
6. dry with materialdried over Na2SO4
7. customThe solution was dried under vacuum
8. customto yield an oily product which

ORD record

ord-f836df70c9fb4dd9ae8a5e55cf465066

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08242162B2