Imidazole → HCID 11791482, compound

Temperature

40 °C

Sodium hydride (11.0 g of 60 wt % dispersion in mineral oil, 276 mmol) was added to a 500-mL, 3-neck round bottom flask equipped with stir bar and reflux condenser under argon purge. Anhydrous tetrahydrofuran (300 mL) was vacuum-transferred into the reaction vessel. Imidazole (15.0 g, 221 mmol) was added to the stirred slurry. The reaction was heated to 40° C. and held there until H2 gas evolution had visibly ceased. After this time, 1,8-dibromooctane (20.4 mL, 111 mmol) was injected into the reaction mixture and the reaction heated at reflux (65° C.) under argon overnight. The reaction was allowed to cool to room temperature and the solids were filtered and washed with tetrahydrofuran. The product solution was concentrated by rotary evaporation and then dissolved in methanol (100 mL). Addition of methanol caused residual mineral oil to separate from the product. The methanol solution was washed with hexanes (3×100 mL), and concentrated by rotary evaporation. The product was dried under vacuum overnight to yield an off-white waxy solid. Yield: 21.5 g (85%).

1. customequipped
2. temperaturereflux condenser under argon
3. custompurge
4. temperaturethe reaction heated
5. temperatureat reflux (65° C.) under argon overnight
6. temperatureto cool to room temperature
7. filtrationthe solids were filtered
8. washwashed with tetrahydrofuran
9. concentrationThe product solution was concentrated by rotary evaporation
10. dissolutiondissolved in methanol (100 mL)
11. additionAddition of methanol caused residual mineral oil
12. customto separate from the product
13. washThe methanol solution was washed with hexanes (3×100 mL)
14. concentrationconcentrated by rotary evaporation
15. customThe product was dried under vacuum overnight
16. customto yield an off-white waxy solid

ORD record

ord-2b771f99c1494eb49026ecc28bf0323d

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07931824B2