Category: 934-22-5

934-22-5, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 934-22-5 as follows.

Example 133; N-1H-Benzimidazol-5-yl-4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide; (1) 2,2,2-Trichloroethyl 1H-benzimidazol-5-ylcarbamate; To a solution of 1H-benzimidazol-5-amine (1.00 g, 7.51 mmol) and pyridine (0.73 ml, 9.01 mmol) in tetrahydrofuran (25 ml) was added, under ice-cooling, 2,2,2-trichloroethyl chloroformate (1.25 ml, 9.01 mmol), and the mixture was stirred at room temperature for 1.5 hour . Water was poured to the reaction mixture, and the resulting solution was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Hexane was poured to the residue, and 1.49 g (64.4%) of the desired product as a solid was separated by filtration. 1H-NMR (CDCl3) delta; 5.22 (2H, s), 7.27 – 7.29 (1H, m), 7.90 – 8.01 (2H, m), 8.06 (1H, br s), 8.56 (1H, s), 10.16 (1H, br s).

According to the analysis of related databases, 6-Aminobenzimidazole, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1813606; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

934-22-5, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 934-22-5, name is 6-Aminobenzimidazole, A new synthetic method of this compound is introduced below.

Compound 216; 1 -(1 H-Benzoimidazol-5-yl)-4-benzylimino-5-(4-bromo-phenyl)- imidazolidin-2-one; 1 H-Benzoimidazol-5-ylamine (1 mmol) and 4-Bromobenzaldehyde (1 mmol) were combined in methanol (2 ml, dry). After 2 hours 2ml of a solution of KOCN (KSCN) (2mmol) and Pyridinehydrochloride (2mmol) in MeOH is added was added. Finally 3- Benzylisocyanide (1 mmol) is added. The reaction was stirred at room temperature for 48h. After evaporation of the solvent the residue was purified with chromatographic methods. Yield: 0.230 g (50 %); mp: 244C, 1H-NMR (500 MHz, DMSO-D6): 4.46 (t, 3J=5.1 Hz, 2 H, CH2), 6.18 (s, 1 H, CH-N), 7.17 (m, 8 H, Ar), 7.39 (d, 3J=8.7 Hz, 1 H, Benzimid), 7.48 (dd, 3J=6.6 Hz, 4J=1.9 Hz, 2 H, Ar), 7.67 (s, br., 1 H, NH), 8.08 (s, 1 H, Benzimid), 8.67 (t, 1 H, Ar), 12.36 (s, br., 1 H, NH). . MS m/z 460.3 (M+H)+, HPLC (254 nm): rt 2.86 min (100 %)molecular weight (g/mol): 460.34 IC50 hQC (nM): 22

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; PROBIODRUG AG; WO2008/55947; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 934-22-5, name is 6-Aminobenzimidazole, belongs to imidazoles-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 934-22-5, 934-22-5

General procedure: [0205] A solution of benzimidazol-5-amine (1 eq.) in DMF (5 ml) was treated with K2CO3 (2.2 eq.) and the respectivealkylhalide (2.2 eq.) and stirred at room temperature for 24 h. The mixture was diluted with water and extracted by meansof ethyl acetate (3×25 ml). The combined organic layers were dried over Na2SO4, evaporated and the residue waspurified by flash chromatography on silica using a CHCl3/MeOH gradient; Example 20 N,N-Bis((4-methylbenzyl)-1H-benzo[d]imidazol-5-amine The compound was synthesized starting from benzimidazol-5-amine (133 mg; 1 mmol; 1 eq.), 4-methylbenzylbromide (407 mg; 2.2 mmol; 2.2 eq.) and K2CO3 (304 mg; 2.2 mmol; 2.2 eq.) according to method 5; Yield: 0.109 g (32.0%); MS m/z: 342.1 [M+H]+; 1H-NMR (500 MHz, DMSO d6): delta 2.23 (s, 6H); 4.57 (s, 4H); 6.66 (br s, 1 H); 6.71 (dd, 1 H, 4J=2.1 Hz, 3J=8.9 Hz); 7.09 (d, 4H, 3J=7.9 Hz); 7.14 (d, 4H, 3J=7.9 Hz); 7.30 (d, 1 H, 3J=8.5 Hz); 7.88 (s, 1 H); 11.88 (br s, 1 H); HPLC (METHOD [A]): rt 17.36 min (98.1%)

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, 6-Aminobenzimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Probiodrug AG; HEISER, Ulrich; RAMSBECK, Daniel; HOFFMANN, Torsten; BOEHME, Livia; (99 pag.)EP2560953; (2016); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

The chemical industry reduces the impact on the environment during synthesis 934-22-5, name is 6-Aminobenzimidazole, I believe this compound will play a more active role in future production and life. 934-22-5

2,3-Dibromo-5-ethoxy-6-hydroxybenzaldehyde (0.1 g, 0.31 mmol), 5-Aminobenzimidazole (0.03 g, 0.20 mmol), and isoamyl alcohol (2 mL) were stirred at room temperature under N2. Acetic acid (0.07 mL) was added drop-wise, and the mixture was refluxed overnight. The reaction mixture was filtered, washed with CH2Cl2, MeOH, and dried to yield 29 (0.06 g, 0.13 mmol, 65.4%) as an orange powder. 1H NMR (DMSO, 300 MHz) delta 15.57 (s, 1H), 12.50 (bs, 1H), 9.20 (s, 1H), 8.31 (s, 1H), 7.81-7.68 (m, 2H), 7.38 (s, 1H), 7.35 (s, 1H), 4.10 (q, 2H, J=6.9 Hz), 1.36 (t, 3H, J=6.9 Hz); 13C NMR (DMSO, 700 MHz) delta 162.36, 154.82, 148.63, 144.23, 140.92, 120.40, 119.77, 117.69, 117.42, 117.30, 116.15, 113.00, 111.88, 104.91, 65.01, 15.00. Rf=0.48 (CH2Cl2/MeOH 9:1)

The chemical industry reduces the impact on the environment during synthesis 934-22-5. I believe this compound will play a more active role in future production and life.

Reference:
Article; Shim, Hyun Jae; Yang, Hye Ran; Kim, Han Ie; Kang, Shin-Ae; No, Kyoung Tai; Jung, Young Hoon; Lee, Seung-Taek; Bioorganic and Medicinal Chemistry Letters; vol. 24; 19; (2014); p. 4659 – 4663;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem