1-Iodopropane → 5-Methyl-1-propylimidazole

Temperature

80 °C

To a solution of 4-methyl-1-triphenylmethylimidazole (20.0 g) in THF (300 ml) and acetonitrile (300 ml) was added 1-iodopropane (26.2 g) and the mixture was stirred overnight under nitrogen atmosphere at 80° C. The solvent was distilled off under reduced pressure and the residue was dissolved in acetic acid (200 ml), and the mixture was stirred for 3 hours under nitrogen atmosphere at 60° C. The mixture was allowed to be at room temperature, water was added to the mixture, and the insolubles were filtered off. Potassium carbonate was added to the filtrate to make it basic and the mixture was extracted with chloroform three times, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the obtained oil was distilled off under reduced pressure (1.5 mmHg, 72° C. to 73° C.), to give 5-methyl-1-propylimidazole (1.9 g) as colorless oil.

1. distillationThe solvent was distilled off under reduced pressure
2. dissolutionthe residue was dissolved in acetic acid (200 ml)
3. stirringthe mixture was stirred for 3 hours under nitrogen atmosphere at 60° C
4. customto be at room temperature
5. additionwater was added to the mixture
6. filtrationthe insolubles were filtered off
7. additionPotassium carbonate was added to the filtrate
8. extractionthe mixture was extracted with chloroform three times
9. dry with materialdried over magnesium sulfate
10. distillationThe solvent was distilled off under reduced pressure
11. distillationthe obtained oil was distilled off under reduced pressure (1.5 mmHg, 72° C. to 73° C.)

ORD record

ord-e89ebc77cc4844f494aac1012389e45e

Source dataset

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07262185B2