Application of 615-16-7, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 615-16-7, name is 2-Hydroxybenzimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.
Under N2 protection, 2(3H)-benzimidazolone 2 (20 g, 149 mmol) was dissolved in CH2Cl2 (75 mL). The solution was cooled to 5 oC and AlCl3 (48 g, 358 mmol) was carefully added as a solid in three equal portions over 10 min. Then ,2-chloropropionyl chloride 3 (21 g, 169 mmol) was added dropwise. After the addition, the reaction mixture was warmed up and stirred for 17 h at room temperature. Then, AlCl3 (10 g, 75 mmol) was added and the reaction mixture was stirred for 2 h at 25 oC. The reaction mixture was slowly poured into acooled mixture (pre-cooled to 5 oC) of heptane (300 mL) and H2O (300 mL). The result mixture was stirred for 15 h at 25 oC. Filtration of the mixture gave a wet cake, which was washed by H2O (200 mL), followed by heptane (100 mL). The resulting cake was dried over 50 oC for 3 h to give compound 4 (33 g,98%); a brown solid; mp 142-144 oC; IR (KBr, max cm-1): 3197, 3095, 2987, 2857, 1750, 1674, 1473,1276, 1201, 872, 708 cm-1; 1H-NMR (400 MHz, DMSO-d6): = 1.60 (d, J = 4.8 Hz, 3H), 5.75 (q, J = 4.8Hz, 1H), 7.06 (d, J = 6.3 Hz, 1H), 7.55 (s, 1H), 7.66 (d, J = 6.3 Hz, 1H), 10.98 (br s, 1H), 11.16 (br s, 1H)ppm; 13C-NMR (100 MHz, DMSO-d6): = 20.62, 53.66, 108.63, 109.14, 123.86, 127.02, 130.37, 135.23,155.90, 193.11 ppm; HRMS (ESI): calcd. for C10H10ClN2O2 225.0431 [M+H]+; found 225.0431. Anal.Calcd for C10H9ClN2O2: C, 53.47; H, 4.04; Cl, 15.78; N, 12.47. Found: C, 53.40; H, 3.95; Cl, 15.71; N,12.38.
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-Hydroxybenzimidazole, other downstream synthetic routes, hurry up and to see.
Reference:
Article; Zou, Ping; Hu, Lin; Yan, Xi-Meng; Li, Xiao-Yue; Wei, Wanguo; Qiu, Xiao-Long; Gou, Shao-Hua; Heterocycles; vol. 98; 5; (2019); p. 674 – 680;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem