Category: 5465-29-2

Electric Literature of 5465-29-2, These common heterocyclic compound, 5465-29-2, name is 2-Propylbenzimidazole, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To 50 ml of water, 450 ml of concentrated sulfuric acid (i.e., 90% concentration) was added dropwise, 50.0 g of 2-propylbenzimidazole was added, and 300 ml of a 30% aqueous solution of hydrogen peroxide was added dropwise. The reaction was exothermic to reflux and the dropping speed was maintained to keep the reaction solution boiling.After completion, the reaction was continued for 3 hours.Add water 400ml, cold to room temperature.The solid was precipitated and stirred at 0-5 C for 3 hours, filtered, washed with water, washed with 100% of 5% sodium sulfite aqueous solution and dried to constant weight to give 2-propylimidazole-4,5-dicarboxylic acid as a white solid (21.7 g, 35%), HPLC purity 89.4%,

The synthetic route of 5465-29-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Huanggang LUBAN Pharmaceutical Co.,Ltd. (LUBAN); YANG, XIAOLONG; LIU, XIANGQUN; LI, QIANG; CHEN, QIAN; YANG, TIEBO; (17 pag.)CN104262260; (2016); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 5465-29-2, name is 2-Propylbenzimidazole, A new synthetic method of this compound is introduced below., Safety of 2-Propylbenzimidazole

The 1H-benzo[d]imidazole 5a(2.50 mmol) was dissolved in 10 ml of abs. DMF. Sodium hydride(60% dispersion in mineral oil) (0.2 g, 5 mmol) was added withcooling. After the gas formation stopped, 40-bromomethyl-[1,10-biphenyl]-2-carbonitrile dissolved in 2 ml of abs. DMF was addeddropwise and the solutionwas stirred for 1 h under cooling in an icebath and further 2 h at RT. Water was added and after the solutionwas acidified with HCl, the product was extracted three times withmethylene chloride. The combined organic layers were dried overNa2SO4 and evaporated to dryness in vacuo. The crude product waspurified by column chromatography on silica gel with methylenechloride/methanol (95:5) and recrystallized from diethyl ether/methanol.

The synthetic route of 5465-29-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Obermoser, Victoria; Urban, Margarethe E.; Murgueitio, Manuela S.; Wolber, Gerhard; Kintscher, Ulrich; Gust, Ronald; European Journal of Medicinal Chemistry; vol. 124; (2016); p. 138 – 152;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 5465-29-2,Some common heterocyclic compound, 5465-29-2, name is 2-Propylbenzimidazole, molecular formula is C10H12N2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

[Example 116] (E)-2-Fluoro-8-(2-propylbenzimidazol-1-yl)methyl-11-[1-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)ethylidene]-6,11-dihydrodibenzo[b,e]oxepine(compound 116) [step 1] (E)-2-(2-Fluoro-8-hydroxymethyl-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene)propiononitrile (0.115 g, 0.299 mmol) obtained in Reference Example B12 was dissolved in THF (1.5 mL), 2,6-lutidine (0.21 mL, 1.79 mmol), lithium bromide (0.156 g, 1.79 mmol) and methanesulfonic anhydride (0.130 g, 0.747 mmol) were added, and the mixture was stirred at room temperature for 16 hr. Water was added to the mixture and the mixture was extracted 3 times with ethyl acetate. The combined organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give a residue. 2-Propylbenzimidazole (0.032 g, 0.199 mmol) was dissolved in DMF (1.5 mL), potassium carbonate (0.125 g, 907 mmol) was added and the mixture was stirred for 15 min. To this mixture was added the residue obtained above, and the mixture was stirred at 60C for 2 hr. Water was added to the mixture and the mixture was extracted 3 times with ethyl acetate. The combined organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) to give (E)-2-[2-fluoro-8-(2-propylbenzimidazol-1-yl)methyl-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene]propiononitrile (0.063 g, 48%).

The synthetic route of 5465-29-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kyowa Hakko Kirin Co., Ltd.; EP2327690; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 5465-29-2,Some common heterocyclic compound, 5465-29-2, name is 2-Propylbenzimidazole, molecular formula is C10H12N2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

[Example 117] (E)-5-[1-(5-Oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)ethylidene]-2-(2-propylbenzimidazol-1-yl)methyl-5,11-dihydrobenzooxepino[3,4-b]pyridine (compound 117) [step 1] (E)-2-(2-Hydroxymethyl-5,11-dihydrobenzooxepino[3,4-b]pyridine)propiononitrile (0.190 g, 0.683 mmol) obtained in Reference Example B10 was dissolved in THF (3 mL), 2,6-lutidine (0.480 mL, 4.16 mmol), lithium bromide (0.360 g, 4.16 mmol) and methanesulfonic anhydride (0.297 g, 1.71 mmol) were added, and the mixture was stirred at room temperature for 16 hr. Water was added to the mixture and the mixture was extracted 3 times with ethyl acetate. The combined organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give a residue. 2-Propylbenzimidazole (0.093 g, 0.581 mmol) was dissolved in DMF (2 mL), potassium carbonate (0.364 g, 2.64 mmol) was added and the mixture was stirred for 15 min. To this mixture was added the residue obtained above, and the mixture was stirred at 60C for 2 hr. Water was added to the mixture and the mixture was extracted 3 times with ethyl acetate. The combined organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1) to give (E)-2-[2-(2-propylbenzimidazol-1-yl)methyl-5,11-dihydrobenzooxepino[3,4-b]pyridin-5-ylidene]propiononitrile (0.180 g, 63%).

The synthetic route of 5465-29-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kyowa Hakko Kirin Co., Ltd.; EP2327690; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 5465-29-2, name is 2-Propylbenzimidazole, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 2-Propylbenzimidazole

[Example 1] (E)-[2-(2-Propylbenzimidazol-1-yl)methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene]acetonitrile (compound 1) (E)-2-(2-Bromomethyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)acetonitrile (648 mg, 2.00 mmol) obtained in Reference Example B1 and 2-propylbenzimidazole (385 mg, 2.40 mmol) were dissolved in DMA (2 mL), potassium carbonate (553 mg, 4.00 mmol) was added, and the mixture was stirred at room temperature for 14 hr. Water was added to the mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=97/3) to give the title compound (compound 1) (778 mg, 96%). ESI-MS m/z: 404 (M + H)+; 1H-NMR (CDCl3, delta): 1.01 (t, J = 7.4 Hz, 3H), 1.85-1.90 (m, 2H), 2.79 (t, J= 7.6 Hz, 2H), 3.06 (br s, 4H), 5.29 (s, 2H), 5.67 (s, 1H), 6.79-6.88 (m, 2H), 7.11-7.35 (m, 7H), 7.43 (dd, J = 7.3, 1.7 Hz, 1H), 7.76 (d, J = 7.3 Hz, 1H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 5465-29-2.

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. 5465-29-2, name is 2-Propylbenzimidazole, A new synthetic method of this compound is introduced below., Quality Control of 2-Propylbenzimidazole

2-Propyl-benzimidazole (0.30 g, 1.87 mmol) was dissolved in acetonitrile (7 mL), potassium hydroxide (0.17 g, 3.03 mmol) was added, and the mixture was refluxed for 30 min. 2-(Bromomethyl)naphthalene (0.42 g, 1.90 mmol) was added and the mixture was refluxed overnight.

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:
Article; Shelton, Kerri L.; DeBord, Michael A.; Wagers, Patrick O.; Southerland, Marie R.; Williams, Travis M.; Robishaw, Nikki K.; Shriver, Leah P.; Tessier, Claire A.; Panzner, Matthew J.; Youngs, Wiley J.; Bioorganic and Medicinal Chemistry; vol. 25; 1; (2017); p. 421 – 439;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 5465-29-2, 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 5465-29-2 as follows.

General procedure: To the reaction vessel containing benzimidazole or imidazole (1mmol), alkyl halide (1mmol), 50% NaOH (0.5mL) and anionic surfactant sodium dodecyl sulfate (5mol%) was added and the reaction mixture was vigorously stirred at room temperature or 60C. After the completion of reaction (TLC) followed by standard workup using ethyl acetate as extracting solvent the crude product was purified over silica-gel (60-120 mesh) using ethyl acetate-hexane (3:7) as eluent to afford pure products. Identities of the products were judged by the comparison of melting point, IR data, 1H NMR, 13C NMR and HRMS analyses.

According to the analysis of related databases, 5465-29-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Chakraborty, Ankita; Debnath, Sudipto; Ghosh, Tanmoy; Maiti, Dilip K.; Majumdar, Swapan; Tetrahedron; vol. 74; 40; (2018); p. 5932 – 5941;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 5465-29-2, name is 2-Propylbenzimidazole, molecular formula is C10H12N2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Recommanded Product: 2-Propylbenzimidazole

General procedure: A solution of 10.0 mmol of compound 1a-1d in 14 mL of concentrated sulfuric acid was heated to 100-105C, 14 mL (0.26 mol) of 30% aqueous hydrogen peroxide was added dropwise with stirring,and the mixture was stirred for 1 h at 130C. After cooling, the mixture was poured into water and adjusted to pH 4, and the precipitate was filtered off.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5465-29-2, its application will become more common.

Reference:
Article; Brusina; Nikolaev; Ramsh; Piotrovskii; Russian Journal of Organic Chemistry; vol. 52; 10; (2016); p. 1528 – 1530; Zh. Org. Khim.; vol. 52; 10; (2016); p. 1533 – 1535,3;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 5465-29-2, name is 2-Propylbenzimidazole, 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 5465-29-2, COA of Formula: C10H12N2

General procedure: To a solution of [DodecIm][HSO4]* (5.00 mol%, 16.7 mg) in 95% EtOH (5.00 mL) was added aldehyde (2) (1.00 mmol) and o-phenylenediamine (1a) (1.20 mmol, 129.8 mg) or 2-amino-4-fluoroaniline (1c) (1.20 mmol, 151.2 mg) at room temperature respectively. The reaction mixture was stirred at room temperature for 12 h and then ethanol solvent was removed by rotary evaporator. The crude residue was diluted with water (5.00 mL)No. and extracted with ethyl acetate (3 * 5 mL). The combine organic layer was concentrated using rotary evaporator. Then crude residue was dissolved in acetonitrile (5.00 mL), followed by adding KOH (2.00 mmol, 112 mg) and alkyl halide (2.00 mmol) at room temperature respectively. The reaction mixture was stirred at room temperature for 0.5-24 h. After the reaction completed, the reaction mixture was neutralized with sat. NH4Cl and extracted with ethyl acetate (3 * 15 mL). The combine organic layer was dried over sodium sulfate anhydrous and concentrated using rotary evaporator. The crude product was purified by column chromatography (SiO2, 10-50% ethyl acetate/n-hexane as eluent depend on each derivatives) to give the desired products 5a-5z. *Recycling experiment. After extraction, the water layerNo. was removed to give the catalyst III. Recovered catalyst III was reused directly by adding EtOH and substrates in the next run without purification. Spectral data of compounds 5b [24], 5c [24], 5l [3c], 5o [26], and 5q [25], were previously described in the literature.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Propylbenzimidazole, and friends who are interested can also refer to it.

Reference:
Article; Senapak, Warapong; Saeeng, Rungnapha; Jaratjaroonphong, Jaray; Promarak, Vinich; Sirion, Uthaiwan; Tetrahedron; vol. 75; 26; (2019); p. 3543 – 3552;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 5465-29-2, The chemical industry reduces the impact on the environment during synthesis 5465-29-2, name is 2-Propylbenzimidazole, I believe this compound will play a more active role in future production and life.

2-Propyl-1H-benzo[d]imidazole (Synthetic Communication, 2002, vol. 32, p3703, 246 mg, 1.54 mmol) and (E)-2-[8-(bromomethyl)-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene]propanenitrile (550 mg, 1.54 mmol) obtained in Reference Example 1 were dissolved in DMF (7 mL), potassium carbonate (1.06 g, 7.68 mmol) was added and the mixture was stirred overnight. To the mixture was added water (20 mL), and the precipitated crystals were collected by suction filtration to give the title compound (640 mg, 94%). ESIMS m/z: 438 (M + H)+; 1H NMR (300 MHz, CDCl3,delta): 1.02 (t, J = 7.4 Hz, 3H), 1.77-1.97 (m, 2H), 2.23 (s, 3H), 2.80 (t, J = 7.4 Hz, 2H), 4.73 (d, J = 12.6 Hz, 1H), 5.32-5.48 (m, 3H), 6.51-6.58 (m, 1H), 6.59-6.69 (m, 1H), 6.94-7.07 (m, 3H), 7.11-7.29 (m, 3H), 7.43 (d, J = 7.8 Hz, 1H), 7.78 (d, J = 7.5 Hz, 1H)

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

Reference:
Patent; Kyowa Hakko Kirin Co., Ltd.; YAMAMOTO, Keisuke; TAMURA, Tomohiro; NAKAMURA, Rina; UENO, Kimihisa; HOSOE, Shintaro; EP2740730; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem