Tag: M.W=300-400

Electric Literature of 152628-02-9, 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. 152628-02-9 name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, 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.

90 gm of BIM in 500 ml DMF was added at about 150C followed by addition of 41.4 gm potassium tertiary butoxide and stirred for about 15-20 minutes at 15-200C. 138.7 gm of Ethyl-4-(bromomethyl) biphenyl-2-carboxylate in 250 ml DMF was added slowly over 45 to 60 minutes maintaining temperature 15-200C. The reaction mixture was stirred for about 30 minutes. 1500 ml of Ethyl acetate and 2000 ml water were added to the reaction mixture at 20-300C and the layer was allowed to separate. Aqueous layer was extracted with 1000 ml of ethyl acetate. The combined organic layer was washed with water [3 X 1000 ml]. The organic layer was dried over anhydrous sodium sulfate and dried ethyl acetate solution was filtered. The ethyl acetate was removed by distillation under vacuum at 50-550C. 500 ml of fresh ethyl acetate was added to the residue to make a solution at 60-650C. The reaction mixture was cooled to 50-550C. 200 ml of hexane was added and stirred for 30 minutes. The reaction mixture was cooled to 100C and further stirred for about 1 hour at 5-10 C.The material was filtered and washed with a mixture of ethyl acetate and 200 ml hexane (7:3 v/vl) at 8-120C. The wet cake was dissolved in 600 ml ethyl acetate at 60-650C and cooled to ~50 0C. 240 ml of hexane was added and mixture was cooled with stirring to 100C and then stirred for about one hour. The material was filtered and washed with a mixture of 120 ml Ethyl acetate and hexane (7:3 v/v) at 8-12 C. The material was suction dried and used as such. 108.2 gm of product is obtained with 99.6 % purity (By HPLC).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, and friends who are interested can also refer to it.

Reference:
Patent; CADILA PHARMACEUTICALS LTD.; KHAMAR, Bakulesh, Mafatlal; SIDDIQUI, Ishrat, Husain; PONNAIAH, Ravi; MODI, Indravadan, Ambalal; WO2010/18441; (2010); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 103057-10-9, These common heterocyclic compound, 103057-10-9, name is 4-(Chloromethyl)-1-trityl-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.

Step D 4-Diethylphosphonomethyl-1-triphenylmethylimidazole The product from Step C is dissolved in acetonitrile and cooled to 0 C. Triethyl phosphite (1 equivalent) and sodium iodide (1 equivalent) are added, and the reaction stirred at room temperature overnight. The reaction is quenched with ammonium chloride, and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and concentrated to provide the title compound.

The synthetic route of 103057-10-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US5891889; (1999); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 2034-22-2, 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. 2034-22-2, name is 2,4,5-Tribromoimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a reaction flask were added 2,4,5-tribromo-1H-imidazole 9(3 g,10 mmol), sodium sulfite (6.3 g, 50 mmol) and 30 mLwater andthen heated at 110 C for 6 h. After cooling to room temperature, theproduct precipitated as a yellowish solid was filtered and theaqueous phase was extracted by ethyl acetate (3 30 mL). Thecombined organic extracts were washed with water (3 30 mL)and dried over anhydrous magnesium sulfate. Ethyl acetate wasremoved by rotary evaporator and yellowish solid 10 was obtained(1.25 g, 85% yield); mp: 131-132.5 C (lit. mp 130-131 C) [43].

The synthetic route of 2,4,5-Tribromoimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shirvani, Pouria; Fassihi, Afshin; Saghaie, Lotfollah; Van Belle, Siska; Debyser, Zeger; Christ, Frauke; Journal of Molecular Structure; vol. 1202; (2020);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 2620-76-0, 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 2620-76-0 as follows.

Example 5In Example 5, an example of a synthesis method of 4-(9H-carbazol-9-yl)-4′-(1-phenyl-1H-benzo[d]imidazol-2-yl)triphenylamine (abbreviation: YGABIm) which is represented by a structural formula (227) will be described. A synthesis scheme is shown in the following (E5-1). In a 100 mL three-necked flask were placed 1.0 g (2.7 mmol) of 2-(4-bromophenyl)-1-phenyl-1H-benzo[d]imidazole, 0.96 g (2.7 mmol) of 4-(carbazol-9-yl)diphenylamine (abbreviation: YGA), 0.60 g (6.3 mmol) of sodium tert-butoxide, and 0.050 g (0.086 mmol) of bis(dibenzylideneacetone)palladium(0), and the atmosphere in the flask was replaced with nitrogen.To this mixture were added 15 mL of toluene and 0.050 mL of a 10percent hexane solution of tri(tert-butyl)phosphine. This mixture was stirred at 80° C. for 5 hours. After the stirring, toluene was added to this mixture, and this suspension was subjected to suction filtration through Celite to give a filtrate. The obtained filtrate was washed with water, a saturated sodium hydrogen carbonate solution, and a saturated saline solution in this order. Then, the organic layer and the aqueous layer were separated, and magnesium sulfate was added to dry the organic layer. This mixture was subjected to suction filtration so that the magnesium sulfate was removed to give a filtrate. The obtained filtrate was concentrated to give a compound. The obtained compound was purified by silica gel column chromatography. The silica gel column chromatography was performed by, first, using toluene as a developing solvent, and then using a mixed solvent of toluene and ethyl acetate (toluene:ethyl acetate=5:1) as a developing solvent. The obtained fraction was concentrated to give a compound. The obtained compound was recrystallized with a mixed solvent of chloroform and hexane to give 1.2 g of a light yellow powdered solid in a yield of 74percent.Then, 1.2 g of the obtained solid was sublimated and purified by train sublimation. The sublimation purification was performed under a reduced pressure of 2.7 Pa, with a flow rate of argon at 5 mL/min, at 261° C., and for 14 hours. After the sublimation purification, 1.0 g of a target substance was obtained in a yield of 83percent.By a nuclear magnetic resonance (NMR) method, this compound was confirmed to be 4-(9H-carbazol-9-yl)-4′-(1-phenyl-1H-benzo[d]imidazol-2-yl)triphenylamine (abbreviation: YGABIm), which was a target substance.1H NMR data of the obtained compound is shown below: 1H NMR (CDCl3, 300 MHz): delta=7.30-7.56 (m, 27H), 7.87 (d, J=8.3 Hz, 1H), 8.13 (d, J=7.8 Hz, 2H)

According to the analysis of related databases, 2620-76-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Semiconductor Energy Laboratory Co., Ltd.; US8329917; (2012); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route 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.

Example 4. 4′-[[4-Methyl-6-(1-methyl-2-benzimidazolyl)-2-propyl-1-benzimidazolyl]methyl]-2-biphenylcarboxylic acid (telmisartan) (4′-Methyl-2′-propyl-1H-benzimidazol-6′-yl)-1-methyl benzimidazole (3.0 g, 9.8 mmol), 4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzyl methanesulfonate (3.12 g, 10 mmol), tetrahydrofuran (15 ml) and potassium carbonate (1.38 g, 10 mmol) are loaded into a round-bottom flask equipped with magnetic stirrer, condenser and under nitrogen atmosphere. The mixture is stirred at room temperature for 8 hours, then 10% hydrochloric acid is added to pH=2. THF is evaporated off, which causes precipitation of boronic acid.

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; Dipharma S.p.A.; EP1719766; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[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 152628-02-9, Formula: C19H20N4

l-Ethyl-2-[4′-(bromomethylphenyl)]benzoate (30.30 g, 85.5%) was dissolved in N1N- dimethylformamide (100 ml) at 2 + 20C and 4-methyl-6-(l -methyl- 1-benzimidazolyl)- 2-propyl-l-benzimidazole (25 g) at 2 +/- 20C was added to the above solution followed by sodium hydroxide (3.42 g). Thereafter, stirring was continued at 2 +/- 20C till the completion of the reaction. Methylene chloride (125 ml) was added to the above reaction mass followed by DM water (250 ml, 22 +/- 20C) at 2 +/- 20C. Stirring was continued at 22 +/- 20C for 15 min and the layers were separated and the aqueous layer was extracted with methylene chloride (25 ml) at 22 +/- 20C. The combined organic extract was washed with DM water (125 ml) at 22 +/- 20C and the organic layer was concentrated till the mass temperature reaches to 6O0C at atmospheric pressure. Ethanol (75 ml) was added to the concentrated mass (Contains Telmisartan ethyl ester) at 600C and the concentration was continued till the vapor temperature reaches to 820C. The concentrated mass was cooled to 45 + 5 and diluted with ethanol (100 ml) followed by aqueous sodium hydroxide (prepared by dissolving 10.87 g of sodium hydroxide in 25 ml of DM water) at 45 + 50C in 15 +/- 5 min was added and the contents were heated to reflux at 78 +/- I0C. Thereafter, stirring was continued at reflux temperature (78 +/- I0C) till completion of the reaction. The reaction mass was concentrated at atmospheric pressure till the mass temperature reaches to 80 +/- 20C and DM water (375 ml, 28 +/- 20C) was added to the residue followed by methylene chloride (50 ml) and stirred for 10 min at 22 + 20C. The layers were separated and methylene chloride (200 ml) was added to the aqueous layer at 22 + 20C and pH was adjusted to 4.1 +/- 0.1 with hydrochloric acid (-17 ml, 30%w/w) and stirring was continued for 10 min at 22 +/- 20C. The layers were separated and the organic layer was washed with DM water (50 ml) at 28 + 20C. The organic layer was diluted with LambdazetaN-dimethylformamide (125 ml) at 28 + 20C and seeded with Telmisaratn Form A. Thereafter, the solution was kept on standing at 28 +/- 20C for 30 min and Telmisartan Form A crystallizes out. The resulting slurry was concentrated at atmospheric pressure till the mass temperature reaches to 84 +/- 20C. The slurry was cooled to 2 +/- 20C and stirred for Ih at this temperature. The product was filtered and washed with pre-cooled N,iV-dimethylformamide (25 ml, 0 +/- 20C) followed by pre-cooled ethanol (50 ml, O0C) and dried to obtain Telmisartan (30 g ) was having more than 99.7 % of HPLC purity.

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, 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

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

Adding a certain compound to certain chemical reactions, such as: 15469-97-3, name is 1-Trityl-1H-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 15469-97-3, Application In Synthesis of 1-Trityl-1H-imidazole

Take the imidazole salt (395 mg, 0.5 mmol), 1-trityl imidazole (550 mg, 1.8 mmol), anhydrous potassium carbonate (61 mg, 4.4 mmol), palladium dichloride (78.5 mg, 44 mmol) After vacuuming with nitrogen, anhydrous THF (6 mL) was added and the mixture was refluxed for 20 h. After the reaction solution was cooled to room temperature, it was diluted with dichloromethane, and the crude product was purified by column chromatography.The pale yellow product was obtained 278 mg, yield 53percent.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Trityl-1H-imidazole, and friends who are interested can also refer to it.

Reference:
Patent; Tianjin Normal University; Liu Guiyan; Han Fangwai; Liu Chengxin; Xu Ying; (9 pag.)CN108690086; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 152628-02-9, 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. 152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 3 2-cyano-4?-(2?-n-propyl-4?-methyl-6?-(1??-methylbenzimidazol-2??-yl)benzimidazol-1?-ylmethyl) biphenyl [0023] In a 2 litre reaction flask 500 ml of methyl isobutyl ketone was added followed by 100 gm of 2-n-propyl-4-methyl-6-(1?-methylbenzimidazol-2?-yl)benzimidazole. The reaction mass was stirred and a solution of 40 gm sodium hydroxide in 300 ml water was added. To this solution, 10 gm tetra butyl ammonium hydrogen sulphate and 80 gm of 4-chloromethyl-2?-cyanobiphenyl was added. The reaction mass was warmed to 80 C. and maintained for 4 hours at 80 to 85 C. [0024] The completion of the reaction was monitored by TLC using mobile phase chloroform: methanol (9:1). After completion of the reaction, the mass was cooled to 20 C., maintained 3 hours at 15 to 20 C. The product which precipitated out was filtered, washed with methyl isobutyl ketone, followed by water to yield 126 gm of 2-cyano-4?-(2?-n-propyl-4?-methyl-6?-(1??-methylbenzimidazol-2??-yl)benzimidazol-1?-ylmethyl) biphenyl, melting at 196-198 C. [0025] C 80.53%, H 5.70%, N 14.20%; m/z=496.64 1H NMR DMSO d6 400 Mhz: delta ppm 0.96-0.99 (t, 3H) 1.75-1.84 (m, 2H) 2.62 (s, 3H) 2.89-2.93 (t, 2H) 3.80 (s, 3H) 5.67 (s, 2H) 7.18-7.92 (m, 14H)

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, 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Amarnath, U; Suryakiran, U; US2015/197495; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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.

Add 2-n-propyl-4-methyl-6-( -methylbenzimidazol-2′-yl) benzimidazole 100 g in 1000ml of acetone and of potassium hydroxide 22.0 g with stirring at 20-25C. Then of 4-bromomethyl-2′-cyanobiphenyl 92g is added at 20-25 C. Monitor the reaction on thin layer chromatography, after the reaction is completed, cooled to 0 to 5.0 C. and stirred for another hour at this temperature. The material is filtered, washed with chilled acetone, then wash with water, and then dried in a air drying cupboard at 80 C. Yield: 141.50 g (87.73% of theory); melting point: 196 C.-197 C; HPLC: 99.50%. N-3 isomer: 0.16%.

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; INOGENT LABORATORIES PRIVATE LIMITED; RAY, Purna, Chandra; NIGAM, Satish; PANDEY, Anand, Kumar; PATIL, Premchand; REDDY, Jagan, Mohan; ORUGANTI, Nagaraju; WO2011/77444; (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. 152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole

To a 100 mL flask was added 2-n-propyl-4-methyl-6- (1′-methylbenzimidazol-2-yl) benzimidazole1.0 g (3.3 mmol), N-methylpyrrolidone4 g of potassium tert-butoxide and 0.4 g (3.6 mmol) of potassium tert-And stirring was started with a magnetic stirrer.While cooling to below 10 C.,A solution of 1.2 g (3.5 mmol) of 4′-bromomethylbiphenyl-2-carboxylic acid tert-butyl ester dissolved in 4.1 g of N-methylpyrrolidone was added dropwise over 2 hours. After the dropwise addition, the mixture was stirred at an internal temperature of 0 to 10 C. for 2 hours. As a result of sampling the reaction solution and conducting liquid chromatography analysis, it was found that 2 – n – propyl – 4 – methyl – 6 – (1 ‘- methylbenzimidazol – 2 – yl) benzimidazole was not detected and 4’ – [[4- Methyl-6- (1-methyl-1 H-benzimidazol-2-yl) -2-propyl- 1 H- benzimidazol- 1 – yl] methyl] biphenyl-2-carboxylic acid tert-butyl ester was 86.0% Area percentage) was generated.

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 152628-02-9.

Reference:
Patent; DNP FINE CHEMICALS UTSUNOMIYA COMPANY LIMITED; MATSUMOTO, TAKAFUMI; IKEDA, SHIN; SUZUKI, YOSHINOBU; (12 pag.)JP5711888; (2015); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem