Imidazole → HCID 57339814, compound

Sodium hydride (1.37 g 60% dispersion in oil, 0.82 g; 34.2 mmol) was weighed out in a 100 mL round bottom flask, and washed with hexane (3×15 mL) to remove the mineral oils. DMF (anhydrous, 15 mL) was added to the sodium hydride and the whole was stirred at room temperature for a couple of minutes under N2. 3,3-Dimethylallyl bromide (1.05 g, 7.02 mmol) was added to the reaction mixture, followed by slow addition of imidazole (2.28 g, 33.5 mmol) while cooling in an ice bath. The mixture was a milky cream colour initially, turning into a homogeneous brown solution. Stirring was continued at room temperature for 20 h. When the TLC showed complete consumption of the dimethylallyl bromide, the DMF was distilled off at 120° C. under high vacuum (Kugelrohr), leaving a viscous yellow heterogeneous mixture. This was triturated with chloroform to give a brown organic layer after removing the precipitated solids by filtration. The organic layer was washed with brine (3×20 mL), dried (Na2SO4) and the solvent was removed under reduced pressure and then under high vacuum. This gave the product as a dark brown oil (0.52 g, 54%).

1. washwashed with hexane (3×15 mL)
2. customto remove the mineral oils
3. additionDMF (anhydrous, 15 mL) was added to the sodium hydride
4. temperaturewhile cooling in an ice bath
5. stirringStirring
6. customconsumption of the dimethylallyl bromide
7. distillationthe DMF was distilled off at 120° C. under high vacuum (Kugelrohr)
8. customleaving a viscous yellow heterogeneous mixture
9. customThis was triturated with chloroform
10. customto give a brown organic layer
11. customafter removing the precipitated solids
12. filtrationby filtration
13. washThe organic layer was washed with brine (3×20 mL)
14. dry with materialdried (Na2SO4)
15. customthe solvent was removed under reduced pressure

ORD record

ord-58c964cb936c47b2b82af51c23533a5c

Source dataset

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08038737B2