1-Octylimidazole

Synthesis

Imidazole (1.36 g, 20.0 mmol) was mixed with sodium hydroxide (0.80 g, 20.0 mmol) in DMSO, heated to 90 °C and maintained for 2 h, then cooled to room temperature. A DMSO solution of 1-bromooctane (3.46 g, 19.0 mmol) was added slowly and dropwise to the reaction mixture. The reaction mixture was stirred at room temperature for 3 hours and then gradually warmed to 65 °C and stirred continuously at this temperature for 16 hours. After completion of the reaction, the reaction solution was mixed with water and extracted with ether four times. The ether phases were combined and dried with anhydrous sodium sulfate. The ether was removed by distillation under reduced pressure to give Intermediate 9 as a yellow liquid (2.89 g, 89% yield).1H NMR (DMSO-d6) data were as follows: δ 7.61 (s, 2H), 7.15 (s, 1H), 6.87 (s, 1H), 3.93 (t, 2H), 1.68 (m, 2H), 1.25 (m, 10H), 0.85 (t 3H).

References

[1] Synthetic Communications, 1993, vol. 23, # 13, p. 1783 - 1786
[2] Journal of Physical Chemistry B, 2013, vol. 117, # 48, p. 15014 - 15022
[3] ChemMedChem, 2017, vol. 12, # 11, p. 835 - 840
[4] Patent: WO2018/56902, 2018, A1. Location in patent: Page/Page column 32
[5] Patent: CN103951702, 2016, B. Location in patent: Paragraph 0039; 0040