Imidazole → HCID 20148471, compound

Pent-4-enyl bromide (10 g, 0.067 mole) was added dropwise to a stirred refluxing mixture of imidazole (9 g; 0.132 mole) and sodium bicarbonate (11 g; 0.13 mole) in methanol (50 ml). After addition the mixture was stirred for a further 50 hours under reflux. The reaction mixture was filtered to remove the insoluble matter and the filtrate evaporated to a yellow oil. This oil was taken up in 2M HCl (150 ml) and washed with ether (50 ml). The acid solution was then basified with 10M NaOH (about 30 ml) and extracted with chloroform (3×50 ml). The combined extracts were dried over anhydrous MgSO4 and the solvent removed under vacuum to leave a yellow oil as crude product, which was purified on silica gel column using 10% MeOH/EtOAc as eluent. 1.0 g distilled in vacuo b.p. 132°/12 mm, yield 0.9 g. Micro analysis: C8H12N2 requires C,70.59, H,8.82, N,20.59. Found: C,69.24, H,8.56, N,20.11.

1. temperaturerefluxing
2. additionAfter addition the mixture
3. temperatureunder reflux
4. filtrationThe reaction mixture was filtered
5. customto remove the insoluble matter
6. customthe filtrate evaporated to a yellow oil
7. washwashed with ether (50 ml)
8. extractionextracted with chloroform (3×50 ml)
9. dry with materialThe combined extracts were dried over anhydrous MgSO4
10. customthe solvent removed under vacuum
11. customto leave a yellow oil as crude product, which
12. customwas purified on silica gel column
13. distillation1.0 g distilled in vacuo b.p. 132°/12 mm, yield 0.9 g

ORD record

ord-8189db071bc44089bd5a8813031bf974

Source dataset

uspto-grants-1981_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04284641