Category: 152628-03-0

Related Products of 152628-03-0,Some common heterocyclic compound, 152628-03-0, name is 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid, molecular formula is C12H14N2O2, 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 2; Variant 2; Methanesulphonic acid is heated to about 80 C. At a temperature of 75 C. to 85 C., 2-propyl-4-methyl-1H-benzimidazole-6-carboxylic acid is added. Then at 85 C. to 95 C. N-methyl-o-phenylene-diamine is added.The mixture is heated to110 C. to 130 C. and phosphorus pentoxide is metered in until an internal temperature of not more than 160 C. is reached. Then the mixture is stirred for 3 hours at a maximum temperature of 145 C. It is cooled to <100 C. and water is metered into the reaction mixture. 50% sodium hydroxide solution is added at <100 C. until a pH of less than 3 is obtained.Finally, treatments with charcoal are carried out at <100 C.At a temperature of <80 C. isopropanol is added and the mixture is adjusted with sodium hydroxide solution to a pH between 4.5 and 7. The aqueous phase is separated off. In order to precipitate dimethyl-2'-propyl-2,5'-bi-1H-benzimidazole water is metered in, the contents of the apparatus are cooled to at least 40 C. for technical reasons and the product is isolated.Yield: 78-90% of theoryHPLC purity: >99.5%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid, its application will become more common.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2011/190508; (2011); A1;,
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. 152628-03-0, name is 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid, A new synthetic method of this compound is introduced below., Formula: C12H14N2O2

Compound IIc (534 mg, 2.45 mmol) was slowly added to polyphosphoric acid (15 mL) heated to 80 & lt; 0 & gt; C, stirred and heated to 150 & lt; 0 & gt; C.Compound IIIb (320 mg, 2.94 mmol) was slowly added to the polyphosphoric acid solution of the former several times, and the mixture was stirred at 150 C for 12 h. After completion of the reaction, the reaction solution was poured into 100 mL of ice water and adjusted to pH 8-10 with concentrated aqueous ammonia. A large amount of precipitate appeared, filtered and the filter cake was washed three times with 5% ethanol solution.After drying the filter cake, the resulting filter cake was purified by chromatography to give about 357 mg (yield 58.7%) of the pale yellow compound IVb.

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; Donghua University; Chen Zhilong; Bao Xiaolu; Zhu Weibo; Wu Zhuo; Yan Yijia; Tang Hesheng; Wang Li; Yu Xinhai; Zhu Zhijia; Xu Yongfen; (15 pag.)CN106749319; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

152628-03-0, 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. 152628-03-0, name is 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Preparation 1 7-Methyl-2-propyl-3H-benzoimidazole-5-carboxylic acid ((R)-1-benzyl-2-benzyloxycarbamoylethyl)amide To a solution of 7-methyl-2-propyl-3H-benzoimidazole-5-carboxylic acid (164 mg, 752 mumol) and (R)-3-amino-N-benzyloxy-4-phenylbutyramide (TFA salt: 300 mg, 754 mumol) in DMF (10 mL) containing triethylamine (210 muL), was added HOBt (151 mug, 755 mumol) and EDC (151 mg, 788 mumol). The mixture was stirred at room temperature overnight and concentrated in vacuo, yielding a pale brown residue. The residue was dissolved in DCM (100 mL) and washed sequentially with 1M H3PO4, a saturated NaHCO3 solution, and saturated aqueous NaCl. The organic layer was collected, dried over MgSO4, and concentrated to afford the title compound as a pale yellow oil (150 mg; 41% yield), which was used without further treatment. ESMS [M+H]+ calcd for C29H32N4O3, 485.26; found 485.5.

The synthetic route of 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Choi, Seok-Ki; Fatheree, Paul R.; McKinnell, Robert Murray; Olson, Brooke; US2009/149521; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 152628-03-0, 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. 152628-03-0, name is 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 4-methyl-2-n-propyl-1H-benzimidazole-6-carboxylic (1, 2.18g, 10mmol) and thionyl chloride (20mL, 280mmol) was refluxed for 3h, then the excess thionyl chloride was removed under reduced pressure to obtain the crude acyl chloride (2) as an off-white solid. It was used for the next step directly.

The chemical industry reduces the impact on the environment during synthesis 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zhang, Jun; Wang, Jin-Liang; Yu, Wei-Fa; Zhou, Zhi-Ming; Tao, Wen-Chang; Wang, Yi-Cheng; Xue, Wei-Zhe; Xu, Di; Hao, Li-Ping; Han, Xiao-Feng; Fei, Fan; Liu, Ting; Liang, Ai-Hua; European Journal of Medicinal Chemistry; vol. 69; (2013); p. 44 – 54;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 152628-03-0, 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. 152628-03-0, name is 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Reference Example A3: 4-Methyl-6-(2-oxazolyl)-2-propylbenzimidazole [step 1] 6-Methoxycarbonyl-4-methyl-2-propylbenzimidazole (EP502314; 500 mg, 2.29 mmol) was suspended in ethanol (15 mL), 4 mol/L aqueous sodium hydroxide solution (3.1 mL) was added, and the mixture was stirred under reflux for 7 hr. The mixture was concentrated under reduced pressure, and water (20 mL) was added. Under ice-cooling, the mixture was adjusted to pH 1 with 2 mol/L hydrochloric acid, and extracted with chloroform. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was dissolved in dichloromethane, aminoacetaldehyde dimethylacetal (0.50 mL, 4.58 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (527 mg, 2.75 mmol) and 1-hydroxybenzotriazole (421 mg, 2.75 mmol) were added, and the mixture was stirred at room temperature for 6 hr. To the mixture were added saturated aqueous sodium hydrogen carbonate solution (100 mL) and chloroform (100 mL), and the organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give 6-(2,2-dimethoxyethylcarbamoyl)-4-methyl-2-propylbenzimidazole. ESI-MS m/z; 306 (M + H)+; 1H-NMR (CDCl3, delta): 1.02 (t, J = 7.3 Hz, 3H), 1.82-1.97 (m, 2H), 2.65 (s, 3H), 2.92 (t, J= 7.3 Hz, 2H), 3.45 (s, 6H), 3.64 (t, J = 5.3 Hz, 2H), 4.52 (t, J = 5.3 Hz, 1H), 6.42 (s, 1H), 7.89 (s, 1H).

The synthetic route of 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid 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

Adding a certain compound to certain chemical reactions, such as: 152628-03-0, name is 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-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 152628-03-0, category: imidazoles-derivatives

4-Methyl-2-n-propyl-lH-benzimidazole-6-carboxylic acid (50 gms) is suspended in Poly phosphoric acid (300 gms), temperature is raised and maintained for 30 min at 70 – 750C, N-Methyl-o-phenylenediamine dihydrochloride. (45 gms) is added lot wise over 2 hrs and maintained at temperature of 70 – 750C for lhr. The temperature of the reaction mass is raised and maintained for 10 hrs at 130 – 1350C. Mass temperature is cooled to 7O0C, water (600 ml) is added slowly at temperature of 60 – 9O0C. Temperature of the reaction mass is cooled to 3O0C, pH is adjusted to 8.0 – 8.5 with aqueous ammonia solution. EPO Temperature of the reaction mass is raised, maintained at 50- 550C for 1 hr, filter the solid, wet cake is washed with hot water (200 ml) and unload the wet cake. The above wet cake suspended in water (900 ml), temperature is raised and mixed for 1 hr at 50 – 550C. Filtered the solid, washed with hot water (100 ml) and dried the wet cake at temperature of 70 – 750C till constant weight. The above dry material is suspended in methanol (260 ml), and temperature is raised to 45 – 5O0C, charcoal (6.5 gms) is added and mixed for about 30 min. Insolubles are filtered through hyflow bed, washed the bed with hot methanol (60 ml), collect and cooled the filtrate to 250C. Water (160 ml) is added slowly to the filtrate at temperature of 25 – 350C, Mass temperature is raised, maintained for 1 hr at reflux temperature. Reaction mass temperature is cooled, maintained for 2 hrs at 0 – 50C. The solid obtained is filtered, wet cake is washed with methanol (60 ml), the wet cake is dried at temperature of 70 – 750C till becomes constant weight. The dry weight of 4-Methyl-6(l -methyl benzimidazol-2-yl)-2-n-propyl IH- benzimidazole is 54 gms (Yield 77.4%). Water content by KF is 5.85%.

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; MATRIX LABORATORIES LIMITED; WO2007/10558; (2007); A1;,
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. 152628-03-0, name is 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid, A new synthetic method of this compound is introduced below., Recommanded Product: 152628-03-0

4-Methyl-2-n-propyl-lH-benzimidazole-6-carboxylic acid (50 gms) is suspended in Poly phosphoric acid (300 gms), temperature is raised and maintained for 30 min at 70 – 750C, N-Methyl-o-phenylenediamine dihydrochloride. (45 gms) is added lot wise over 2 hrs and maintained at temperature of 70 – 750C for lhr. The temperature of the reaction mass is raised and maintained for 10 hrs at 130 – 1350C. Mass temperature is cooled to 7O0C, water (600 ml) is added slowly at temperature of 60 – 9O0C. Temperature of the reaction mass is cooled to 3O0C, pH is adjusted to 8.0 – 8.5 with aqueous ammonia solution. EPO Temperature of the reaction mass is raised, maintained at 50- 550C for 1 hr, filter the solid, wet cake is washed with hot water (200 ml) and unload the wet cake. The above wet cake suspended in water (900 ml), temperature is raised and mixed for 1 hr at 50 – 550C. Filtered the solid, washed with hot water (100 ml) and dried the wet cake at temperature of 70 – 750C till constant weight. The above dry material is suspended in methanol (260 ml), and temperature is raised to 45 – 5O0C, charcoal (6.5 gms) is added and mixed for about 30 min. Insolubles are filtered through hyflow bed, washed the bed with hot methanol (60 ml), collect and cooled the filtrate to 250C. Water (160 ml) is added slowly to the filtrate at temperature of 25 – 350C, Mass temperature is raised, maintained for 1 hr at reflux temperature. Reaction mass temperature is cooled, maintained for 2 hrs at 0 – 50C. The solid obtained is filtered, wet cake is washed with methanol (60 ml), the wet cake is dried at temperature of 70 – 750C till becomes constant weight. The dry weight of 4-Methyl-6(l -methyl benzimidazol-2-yl)-2-n-propyl IH- benzimidazole is 54 gms (Yield 77.4%). Water content by KF is 5.85%.

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; MATRIX LABORATORIES LIMITED; WO2007/10558; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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 152628-03-0 as follows. category: imidazoles-derivatives

Stirring blade, a thermometer, three-neck flask 1L fitted with condenser, 4-methyl–2-n-propyl -1H- benzimidazole-6-carboxylic acid 50.0g (229mmol) and polyphosphoric acid added and stirred and 300 g, heated to around 70 C., the reaction solution obtained was stirred for 30 minutes, added in portions over a period N- methyl -O- phenylenediamine 45.0g of (368mmol) 2 hours It was.After adding the entire amount, stirring for 1 hour at around 70 C., and stirred for 5 h warmed to near yet 130. C..After confirming the disappearance of 4-methyl–2-n-propyl -1H- benzimidazole-6-carboxylic acid by HPLC, was cooled to about 70 C., while maintaining the water 600g The temperature of the reaction solution at 70 to 85 C. It was dropped little by little.After the total amount dropwise, 30 C. and cooled to near, pH of the reaction solution with aqueous ammonia was adjusted to be pH 8.3, after stirring for 1 hour warmed to around 50 C., the solid by vacuum filtration It is filtered off and washed the solid was filtered off with water 200g in the vicinity of 50 , to obtain a wet product of light brown crystals.Stirring blade, a thermometer, three-neck flask 1L fitted with condenser, was added and stirred the wet product of the resulting pale brown crystals and water 900 g, after stirring for 1 hour warmed to around 50 C. , vacuum filtered off the solids by filtration, wash the solid was filtered off with 100g of water around 50 C., the resulting wet product was dried for 15 hours under reduced pressure, a pale crude benzimidazole body as brown crystals to obtain a body 60.3g.The crude product of the benzimidazole body was analyzed by HPLC, the purity was 98.20%, the content of methyl benzimidazole body 0.14%, the content of ethyl benzimidazole body with 0.07% there were. stirring blade, a thermometer, three-necked flask 100mL fitted with a condenser, a mixture of a crude product 5.0g of methanol 12g and water 50g benzimidazole body obtained in Production Example 1 was added after stirring on, the addition of hydrochloric acid 2.1g containing hydrogen chloride 0.78 g (21.4 mmol), stirred for 10 minutes at about 25 C., the solid in the reaction solution was confirmed to be dissolved.Then, was added aqueous ammonia 1.1g containing ammonia 0.28 g (16.5 mmol), precipitation of white crystals was confirmed.After stirring for 1 hour at about 25 C., vacuum filtered through the solid was filtered off, the solid was filtered off with water 5g were washed twice and dried for 12 hours at 60 C. under reduced pressure and the resulting wet biomass, to obtain a benzimidazole body 4.2g (13.9mmol) as white crystals.Recovery rate, which is calculated based on the mass of the crude product of the benzimidazole body was 84.4%.As a result of the benzimidazole body obtained was analyzed by HPLC, the purity was 99.56%, the content of methyl benzimidazole body 0.06%, the content of ethyl benzimidazole body 0.02% met.

According to the analysis of related databases, 152628-03-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TOKUYAMA CORPORATION; MIYAOKU, TAKAYUKI; (16 pag.)JP2015/160810; (2015); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 152628-03-0, name is 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-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 152628-03-0, name: 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid

1.2 kg of isoamyl alcohol was added to the reaction flask.Add 2-n-propyl-4-methyl-6-carboxybenzimidazole (400 g, 1.83 mol) and stir.Methanesulfonic acid (176 g, 1.83 mol, 1.0 eq) was added and N-methyl-phenylenediamine hydrochloride (360 g, 1.85 mol) was added.The temperature was raised to 130-135 C to reflux and the reaction was carried out for at least 18 hours until no significant moisture was separated. After the reaction is completed, cool to about 70 C,Add 2000 ml of water, stir, adjust the pH to 6~7 with 30% NaOH solution, stir and cool to 20~25 C after completion, and filter to obtain the product, the yield is 93.0%, and the HPLC purity is 99.6%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Weihai Disu Pharmaceutical Co., Ltd.; Disha Pharmaceutical Group Co., Ltd.; Li Xinfa; Cui Dapeng; (6 pag.)CN104974096; (2019); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 152628-03-0, 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. 152628-03-0 name is 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid, 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.

7-Methyl-2-propyl-3H-benzoimidazole-5-carboxylic acid methyl ester (7a): Sulfuric acid (12 mL, 0.22 mol) was added to 7-methyl-2-propyl-3H-benzoimidazole-5-carboxylic acid (30 g, 136 mmol) dissolved in MeOH (670 mL, 16 mol). The mixture was refluxed for 36 hours and concentrated in vacuo. The recovered material was dissolved in 500 mL EtOAc and washed with a saturated NaHCO3 solution. The organic layer was dried over MgSO4 and concentrated to provide Intermediate (7a) as a brown solid (29.1 g). MS m/z: [M+H+] calcd for C13H16N2O2, 233.1; found 233.2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Theravance, Inc.; US2008/318951; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem