Month: July 2021

Application of 152628-02-9,Some common heterocyclic compound, 152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, molecular formula is C19H20N4, 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.

l-Methyl-2-[4′-(bromomethylphenyl)]benzoate (148.68 g) was dissolved in N,N- dimethylformamide at 2 +/- 20C and 2-n-propyl-4-methyl-6-(r-methylbenzimidazol-2′-yl) benzimidazole (150 g) was added at 2 + 20C followed by sodium hydroxide (20.49 g). Thereafter, stirring was continued at 2 +/- 20C till completion of the reaction. Methylene chloride (750 ml) was added at 2 + 20C followed by DM water (150 ml, 22 +/- 20C) and stirring was continued at 22 +/- 20C for 15 min. The layers were separated and the aqueous layer was extracted with methylene chloride (150 ml) at 22 + 20C. The combined organic extract was washed with DM water (750 ml) at 22 +/- 20C and concentrated the organic layer (~ 1050 ml) till the mass temperature reaches to 54 +/- 20C at atmospheric pressure. Methanol (450 ml) was added to the concentrated mass at 53 +/- 20C. The concentration was continued till the vapor temperature reaches to 63 +/- 20C. The concentrated mass was cooled to 45 +/- 50C and diluted with methanol (600 ml). Aqueous sodium hydroxide (prepared by dissolving 65.22 g of sodium hydroxide in 150 ml DM water) was added at 45 +/- 50C in 15 +/- 5 min. The reaction mixture was heated to reflux at 68 +/- I0C. Thereafter, stirring was continued at reflux temperature (68 +/- I0C) till completion of the reaction. The reaction mass was concentrated at atmospheric pressure till the mass temperature reaches to 80 +/- 20C. DM water (2250 ml, 28 +/- 20C) was added to the residue followed by methylene chloride (300 ml) and stirred for 10 min at 22 + 20C. The aqueous layer was separated, methylene chloride (900 ml) was added to the aqueous layer at 22 + 20C and adjusted the pH to 4.1 +/- 0.1 with hydrochloric acid (-84 ml, 30% w/w) and stirred for 10 min at 22 +/- 20C. The aqueous layer was separated from methylene chloride (150 ml) at 22 + 20C. The organic layer was washed with DM water (300 ml) at 28 +/- 20C. The organic layer (-1200 ml) was diluted with JVjJV- dimethylformamide (750 ml) at 28 + 20C and seeded with Telmisartan Form A. The solution was kept standing for 30 mins and Telmisartan Form A crystallized out at 28 +/- 20C. The resulting slurry was concentrated at atmospheric pressure till the mass temperature reaches to 82 +/- 20C. The slurry was cooled to 2 +/- 20C and stirred for Ih at this temperature. The product was filtered and washed with pre-cooled DMF followed by pre-cooled ethanol to obtain Telmisartan (~275g-wet) having more than 99.7% HPLC purity.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, its application will become more common.

Reference:
Patent; AUROBINDO PHARMA LIMITED; KORRAPATI, Venkata Vara Prasada Rao; INTI, Venkata Subramanyeswara Rao; ANANTA, Rani; MEENAKSHISUNDERAM, Sivakumaran; WO2010/4385; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 39021-62-0,Some common heterocyclic compound, 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde, molecular formula is C5H6N2O, 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.

Scheme 1; tert-Butyl (2-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)-1-methyl-1H-imidazol-5- yl)methyl(2-methoxyethyl)carbamate (46); Step 1. 5-alpha.3-Dioxan-2-yl)-1-methyl-1H-imidazole (38) [Shafiee A., Rastkary N., Jorjani M., Shafaghi B., Arch.Pharm.Pharm.Med.Chem. 2002, 2, 69-76]; To a solution of 1 -methyl- 1 H- imidazole-5-carbaldehyde (2.9 g, 26.3 mmol) in toluene (20 mL) was added propane- 1,3-diol (4.01 g, 52.7 mmol) and CSA (0.306g, 1.317 mmol) and the reaction mixture was heated to reflux with azeotropic removal of the evolved water for 24 hours. The reaction mixture was cooled to RT, diluted with DCM and washed with NaHCO3 solution. It was then dried over Na2SO4, filtered and concentrated. Purification by column chromatography (80% EtOAc in Hexane to EtOAc) afforded 38 (2.53 g, 57% yield) as a yellow oil which solidified on standing to a yellow solid. MS (m/z): 169.2 (M+H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Methyl-1H-imidazole-5-carbaldehyde, its application will become more common.

Reference:
Patent; METHYLGENE INC.; WO2009/26717; (2009); 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. 934-32-7, name is 1H-Benzo[d]imidazol-2-amine, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1H-Benzo[d]imidazol-2-amine

General procedure: A mixture of 2-aminobenzimidazole 7 (1.33 g, 10.0 mmol), 10.0 mmol of the proper alkyl halide, 1.0 g of finely powdered KOH mixed with 2.0 g of anhydrous K2CO3 and acetone (50 mL) was heated at reflux for 3 h, with stirring. The solvent was removed in vacuo and the residue was partitioned between water (100 mL) and CH2Cl2 (100 mL), and the aqueous phase was further extracted twice with CH2Cl2. The combined extracts, dried over anhydrous Na2SO4, after removal of solvent afforded an oily or solid residue which was treated with a small amount of ethyl ether to give compounds 8a-e,l-o as whitish solids which were crystallized from the proper solvent. Only in the case of compound 8f, a preliminary purification by column chromatography [SiO2/ethyl acetate-acetone (1:1)] was necessary to obtain a crystalline compound.

According to the analysis of related databases, 934-32-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Di Braccio, Mario; Grossi, Giancarlo; Signorello, Maria Grazia; Leoncini, Giuliana; Cichero, Elena; Fossa, Paola; Alfei, Silvana; Damonte, Gianluca; European Journal of Medicinal Chemistry; vol. 62; (2013); p. 564 – 578;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 2849-93-6, name is 1H-Benzimidazole-2-carboxylic acid, 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 2849-93-6, name: 1H-Benzimidazole-2-carboxylic acid

To a cold (O0C) solution of lH-benzoimidazole-2-carboxylic acid (42.0 mg; 0.23 mmol) in dry DCM (2 mL) were added oxalyl chloride (90.0 uL; 0.92 mmol) and few drops of DMF. The mixture was allowed to warm to room temperature and the stirring was maintained for 3 hours. The solvent was evaporated under vacuum and the resulting compound was dissolved in DCM (2 mL). This solution was added dropwise to a stirred mixture of N-[4-(2-amino-l,l-dimethyl-ethyl)-phenyl]-3,4-dimethoxy- benzamide (70.0 mg; 0.21 mmol), prepared as described in 26(A) and triethylamine (79 uL; 0.51 mmol) in DCM (2 mL) at O0C. After stirring at room temperature for 16 hours, the precipitate was collected by filtration, re-dissolved in DCM and washed with sat. NaHCO3. The organic phase was dried over Na2SO4, filtered and evaporated to dryness to afford the title compound as a white solid (35.0 mg; 32% yield). 1H NMR (300 MHz, DMSO-d6) delta(ppm): 13.23 (br. s., 1 H), 10.02 (s, 1 H), 8.20 (t, 1 H), 7.72 (m, 2 H), 7.66-7.77 (m, 1 H), 7.62 (dd, 1 H), 7.48-7.59 (m, 1 H), 7.54 (d, 1 H), 7.43 (d, 2 H), 7.18-7.37 (m, 2 H), 7.08 (d, 1 H), 3.85 (s, 3 H), 3.84 (s, 3 H), 3.57 (d, 2 H), 1.34 (s, 6 H)LCMS (RT): 2.10 min (Method G); MS (ES+) gave m/z: 473.27 (MH+). MP: 223-226 0C.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; ADDEX PHARMA SA; WO2008/117175; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 1072-63-5, These common heterocyclic compound, 1072-63-5, name is 1-Vinyl-1H-imidazole, 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.

Typically, 1-vinylimidazole (5 g, 15 mmol) and an excess molar amount of 1-bromododecane (7 g, 7 mmol) were loaded into a 100 mL reactor. The mixture was stirred at room temperature overnight, followed at 60 C for 24 h. After cooling down, the reaction mixture was added dropwise into 250 mL of diethyl ether and white precipitate was formed. The precipitate was filtered off and washed with diethyl ether again and dried at room temperature until constant weight (95% yields). The formed solid was dissolved in 20 mL CH2Cl2 in a 50 mL round bottom flask, and aqueous HBF4 (50%) at a 1.1 + 1 M ratio was slowly dropped into the flask. After one week, [C12vim][BF4] was separated by extraction with distilled water. The organic layer was collected, dried over Na2SO4, filtered and the solvent removed in vacuum to give the product. (0007) [C12vim][Br]: 1H NMR (DMSO-d6, delta ppm): 9.53 (1H), 8.20 (1H), 7.93 (1H), 7.28 (1H), 5.95 (1H), 5.41 (1H), 4.18 (2H), 1.81 (2H), 1.23 (18H), 0.85 (3H). Anal. calculated for C17H31N2Br: C, 50.88; H, 10.95; N, 9.89. Found: C, 57.99; H, 9.35; N, 8.00. (0008) [C12vim][BF4]: 1H NMR (DMSO-d6, delta ppm): 9.45 (1H), 8.18 (1H), 7.91 (1H), 7.27 (1H), 5.93 (1H), 5.41 (1H), 4.17 (2H), 1.81 (2H), 1.25 (18H), 0.85 (3H). 19F NMR (DMSO-d6, delta ppm): -148.73. Anal. calculated for C17H31N2BF4: C, 49.69; H, 10.70; N, 9.66. Found: C, 59.15; H, 9.41; N, 7.85; Br, 0.

Statistics shows that 1-Vinyl-1H-imidazole is playing an increasingly important role. we look forward to future research findings about 1072-63-5.

Reference:
Article; Pourjavadi, Ali; Doulabi, Malihe; Hosseini, Seyed Hassan; Polymer; vol. 53; 25; (2012); p. 5737 – 5742;,
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. 152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, A new synthetic method of this compound is introduced below., Application In Synthesis of 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole

General procedure: To a solution of 1,7′-dimethyl-2′-propyl-1H,3’H-2,5′-bibenzo[d]imidazole 3 (2 mmol) and tetrabutylammonium bromide (0.2 mmol) in benzene (25 mL), a solution of 50% NaOH (25 mL) was added at 0 C followed by the addition of sulfonyl chloride 4 (2.2 mmol). The reaction mixture was stirred vigorously at room temperature for 5-6 h and the reaction was monitored by TLC. After the completion of the reaction, aqueous phase was separated and the organic phase was washed with water (20 mL) and brine (20 mL), dried over anhydrous sodium sulphate and concentrated to give crude products which were purified by column chromatography over silica gel using hexane-EtOAc (6:4) mixture as eluent.

The synthetic route of 152628-02-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Roopashree, Rangaswamy; Mohan, Chakrabhavi Dhananjaya; Swaroop, Toreshettahally Ramesh; Jagadish, Swamy; Raghava, Byregowda; Balaji, Kyathegowdanadoddi Srinivas; Jayarama, Shankar; Basappa; Rangappa, Kanchugarakoppal Subbegowda; Bioorganic and Medicinal Chemistry Letters; vol. 25; 12; (2015); p. 2589 – 2593;,
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. 28890-99-5, name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, A new synthetic method of this compound is introduced below., name: 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole

4.02 g (35.2 mol) trans-cyclohexane-1.2-diamine are added to 800 mg (1.96 mmol) 9-iodobenzimidazolo[2,1-b][1,3]benzothiazole 490 mg (2.35 mmol) 6H-benzimidazolo[1,2-a]benzimidazole, 1.37 g (6.45 mmol) potassium phosphate, 370 mg (0.20 mmol) copper iodide in 10 ml dioxane. The reaction mixture is stirred for 27 h at 100 C under nitrogen and cooled to 25 C. The product is filtered off and washed with water and methanol. 100 ml chloroform is added and the product is stirred for 30 minutes. The solid is filtered off and product precipitating from the chloroform phase is filtered off (yield: 1 10 mg (13 %)). 1 H NMR (400 MHz, CF3COOD): delta 9.24 (s, 1 H), 8.66-8.69 8 (m, 2H), 8.43-8.8.56 (m, 4H), 8.02-8.20 (m, 7H), 7.93-7.95 (m, 1 H). MS (APCI(pos), m/z): 430 (M+1).

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; BASF SE; IDEMITSU KOSAN CO., LTD.; SCHAeFER, Thomas; MURER, Peter; HEINEMEYER, Ute; KOHLSTEDT, Julia; WOLLEB, Heinz; WOLLEB, Annemarie; WATANABE, Soichi; NAGASHIMA, Hideaki; SAKAI, Toshio; LENNARTZ, Christian; WAGENBLAST, Gerhard; WO2015/14791; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 32673-41-9, These common heterocyclic compound, 32673-41-9, name is 4-Imidazolemethanol hydrochloride, 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.

Step 1 Preparation of 1-triphenylmethyl-4-(hydroxymethyl)imidazole To a solution of 4-(hydroxymethyl)imidazole hydrochloride (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vccuo to provide the titled product as a white solid which was sufficiently pure for use in the next step.

The synthetic route of 32673-41-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US6015817; (2000); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 716-79-0, name is 2-Phenyl-1H-benzo[d]imidazole, 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 716-79-0, Recommanded Product: 2-Phenyl-1H-benzo[d]imidazole

General procedure: 2.5 g (12.88 mmol) of 2-phenyl-benzimidazole was dissolved in 30 ml of N,N-dimethylformamide, and 5.3 g (38.6 mmol) of K2CO3 and 2.0 ml (16.7 mmol) of 1-chloro-4-iodobutane were added to the resulting solution, followed by mixing the mixture at a room temperature for 10 hours. The reactant was combined with 100 ml of water and extracted with ethylacetate (70 ml X 5) being washed with water and a sodium hydroxide solution, and then the combined organic layer was dried over anhydrous sodium sulfate and filtered. The solvent was removed from the filtrate under a reduced pressure, and the resulting residue was refined by silica gel column chromatography (n-hexane/ethylacetate=2/1) to obtain 3.5 g (yield 96%) of the title compound.1H NMR (300MHz, CDCl3) delta 1.69(m, 2H), 2.00(m, 2H), 3.43(t, 2H), 4.29(t, 2H), 7.30-7.50(m, 3H), 7.55(m, 3H), 7.72(m, 2H), 7.83(m, 1H); MS(m/e, M+): 285

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-Phenyl-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Lim, Chae Jo; Kim, Nakjeong; Lee, Eun Kyoung; Lee, Byung Ho; Oh, Kwang-Seok; Yoo, Sung-Eun; Yi, Kyu Yang; Bioorganic and Medicinal Chemistry Letters; vol. 21; 8; (2011); p. 2309 – 2312;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 38993-84-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 38993-84-9 name is (1-Methyl-1H-imidazol-5-yl)methanol, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A solution of triphosgene (62 mg, 0.21 mmol) in DCM (4.0 mL) was added to a stirred solution of A13 (prepared as described in: WO 2013/055987; 500 mg, 0.525 mmol) and Et3N (120 mg, 1.18 mmol) in DCM (16 mL) at 20 °C. The resulting mixture was stirred at that temperature for 2 h. A solution of (1-methyl-1H-imidazol-5-yl)methanol (80 mg, 0.709 mmol) in DCM (3 mL) was then added followed by nBu2Sn(OAc)2 (2 drops). The reaction mixture was stirred at 20 °C for 16 h under N2 then was concentrated under reduced pressure. The residue was purified by prep-TLC (DCM/MeOH=30/1) to give A17 as a yellow solid (250 mg, yield: 44percent). LCMS (condition A): RT = 0.97 min, m/z = 1091.6 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (1-Methyl-1H-imidazol-5-yl)methanol, and friends who are interested can also refer to it.

Reference:
Article; Dragovich, Peter S.; Broccatelli, Fabio; Chen, Jinhua; Fan, Peter; Le, Hoa; Mao, Weiguang; Pillow, Thomas H.; Polson, Andrew G.; Wai, John; Xu, Zijin; Yao, Hui; Zhang, Donglu; Bioorganic and Medicinal Chemistry Letters; vol. 27; 23; (2017); p. 5300 – 5304;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem