Month: May 2021

Synthetic Route of 10394-40-8,Some common heterocyclic compound, 10394-40-8, name is 1,6-Dimethyl-1H-benzo[d]imidazole, molecular formula is C9H10N2, 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.

STR44 An aqueous solution (100 ml) of 3.95 g of 1,6-dimethylbenzimidazole and 10 g of potassium permanganate was stirred at 50 C. for 2 hours and 2 g of potassium permanganate was further added to the mixture. The mixture was stirred at 80 C. for further 2 hours. After insoluble matters were filtered off, the filtrate was rendered pH 4 with 1 N hydrochloric acid and concentrated under reduced pressure to give 7.33 g of 1-methylbenzimidazole-6-carboxylic acid as the mixture with potassium chloride. The above compound was heated to reflux in 150 ml of methanol overnight in the presence of 3 ml of conc. sulfuric acid. The reaction solution was concentrated under reduced pressure and water was added to the concentrate.

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

Reference:
Patent; Yamanouchi Pharmaceutical Co., Ltd.; US4977175; (1990); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 17450-34-9, name is Ethyl 2-(1-Imidazolyl)acetate, 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 17450-34-9, Formula: C7H10N2O2

Under a dry argon atmosphere, a solution of 2 (6.05g, 39.2mmol) in dry THF (20mL) was added dropwise to the mixture of lithium aluminum hydride (3.00g, 79.1mmol) and dry THF (60mL) at 0C. The reaction mixture was stirred for 5min at 0C and for 4h at room temperature. Then, water (3mL), 15% sodium hydroxide aqueous solution (3mL), and water (9mL) were separately added dropwise to the reaction mixture at 0C. The resulting reaction mixture was stirred at room temperature for 12h and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography eluted with a mixed solvent of chloroform/methanol (10/1v/v). The fraction with an Rf value of 0.22 was collected and purified by distillation under reduced pressure twice to afford 1-(2-hydroxyethyl)imidazole (Im2OH) as colorless oil (2.386g, 54%)

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:
Article; Ichikawa, Tsukasa; Wako, Tsuyoshi; Nemoto, Nobukatsu; Reactive and functional polymers; vol. 99; (2016); p. 1 – 8;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 30086-64-7, 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 30086-64-7 as follows.

Compound 55 (12.5 g, 80.12 mmol) was dissolved in MeOH (250 ml) and Mel (17.1 g, 120.2 mmol) was added. The resulting mixture was refluxed for 2 h. The volatileswere removed under reduced pressure yielding SC, (13.5 g Yield: 99%) as oWwhite solid that was used without further purification.

According to the analysis of related databases, 30086-64-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NANJING GATOR MEDITECH COMPANY, LTD.; IWANOWICZ, Edwin, J.; (94 pag.)WO2018/31987; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 29518-68-1, 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. 29518-68-1 name is 2-(1H-Benzo[d]imidazol-2-yl)ethanamine, 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.

To a 20 mL scintillation vial was added isoxazolidine 60 (20 mg) and 1-H-benzimidazole-2-ethanamine (72.1 mg) followed by 0.35 M 2-hydroxypyridine solution (0.7 mL). The solution was heated to 50 C. for 19 h and then diluted with ethyl acetate (10 mL) and water (10 mL). The organic layer was separated and concentrated in vacuo. The title compound was purified by preparative TLC (1000 microns, silica) eluting with 95:5 ethyl acetate/methanol to yield 12.7 mg of the desired product as a solid. MS (ESI(+)) m/e 539.0 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(1H-Benzo[d]imidazol-2-yl)ethanamine, and friends who are interested can also refer to it.

Reference:
Patent; Infinity Pharmaceuticals, Inc.; US2006/20004; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 92807-02-8, 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. 92807-02-8, name is Methyl 2-mercapto-1H-benzo[d]imidazole-4-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

(b) [2-BENZYLSULFANYL-1 BBENZIMIDAZOLE-4-CARBOXYLIC] acid amide (40) [0130] Sodium hydride (60% dispersion in mineral oil, 47 mg, 1.18 [MMOL)] was suspended in 2 mL DMF at 0 [C.] To this was added 165 mg of 2-mercapto-1 H- benzimidazole-4-carboxylic acid methyl ester (0.79 [MMOL)] in 2 mL DMF via canula. After rinsing with an additional 2 mL DMF the reaction was stirred for 10 minutes, at which time 115 muL of benzyl bromide (0.97 [MMOL)] was added via syringe. The reaction was stirred overnight, with warming to 23 [C.] After quenching with sat. NH4CI the solvent was removed by evaporation. The resulting crude solid was dissolved in 50 mL water and extracted with EtOAc (x3). The organic layer was dried [(MGS04),] filtered and concentrated. The material was filtered through a plug of silica gel utilizing 5% [ET2O/CH2CI2] as eluent and taken on to the next step. [0131] The methyl ester was converted to the amide using the method described by Jagdman et al. (Synth. Commun. (1990) 20: 1203-1208), with use of 6 equivalents of sodium methoxide, to give 95 mg of product (0.33 [MMOL,] 41 % overall) as a white solid. [0132] IR (KBr) 3443,3148, 3080,3003, 2960,2987, 1660,1597, 1579,1512, 1467, 1404,1244, 976,752, [706 CM~1. 1 H NMR (ACETONE-D6) o 4.] 69 (s, [2H),-6.] 84 (br s, 1 H), 7.22- 7.36 (m, 4H), 7.51-7. 55 (m, 2H), 7.58 (dd, [1H, J=] 1.1, 8.1 Hz), 7.95 (dd, [1H, J=] 1.1, 7.7 Hz), 9.31 (br s, 1 H), 11.91 [(BR S, 1 H). HPLC RT = 6. 137 MIN. HRMS CALCD FOR C15H12N30S+NA] 306. [0677,] found 306.0669. Anal. [(C1SHL3N3OS)] C, H, N, S.

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

Reference:
Patent; PFIZER INC.; WO2003/106430; (2003); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 37619-25-3, The chemical industry reduces the impact on the environment during synthesis 37619-25-3, name is Methyl 1H-benzo[d]imidazole-4-carboxylate, I believe this compound will play a more active role in future production and life.

Into a 100-mL round-bottom flask, was placed a solution of methyl 1H-1,3- benzodiazole-4-carboxylate (500 mg, 2.84 mmol, 1.00 equiv) in N,N-dimethylformamide (60 mL), potassium carbonate (1.1 g, 7.96 mmol, 3.00 equiv), and (2-chloroethyl)dimethylamine hydrochloride (523.6 mg, 3.64 mmol, 1.00 equiv). The resulting solution was stirred overnight at 60 oC in an oil bath then allowed to cool and diluted with 40 mL of sodium chloride (aq). The resulting mixture was extracted with 2×40 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate then concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1:2). This resulted in 100 mg (14%) of methyl 1-[2-(dimethylamino)ethyl]-1H-1,3- benzodiazole-4-carboxylate as a solid

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, Methyl 1H-benzo[d]imidazole-4-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LYCERA CORPORATION; AICHER, Thomas, Daniel; PADILLA, Fernando; TOOGOOD, Peter, L.; CHEN, Shoujun; (331 pag.)WO2016/138335; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 6478-79-1, 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. 6478-79-1, name is 5,6-Dichloro-2-methylbenzimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Triethyl orthoacetate (4.6 g, 1 eq) was added drop wise to a refluxing mixture of 4,5-dichloro-1,2-phenylenediamine (5 g, 1 eq) and a catalytic amount of p-toluenesulfonic acid in toluene (40 mL). The mixture was refluxed for 3 hrs and 5.7 g black solid was collected after evaporation of the solvents under reduced pressure and used directly in the following step without further purification. ESI-MS (m/z) calcd (found): 200.0 (201.1) for [M+H]+. To the crude 5,6-dichloro-2-methyl-benzoimidazole (5.7 g, 1 eq) (see FIG. 9) and grinded potassium hydroxide (4.8 g, 3 eq) in acetone (50 mL) was added iodomethane (5.2 g, 1.4 eq) drop wise and the mixture was stirred overnight. The solvent was evaporated under reduced pressure and the residue was partitioned between dichloromethane (200 mL) and water (200 mL). The aqueous phase was washed two times with dichloromethane (200 mL) and the combined organic phase was dried over Na2SO4 and evaporated to dryness. The crude product was recrystallized from ethyl acetate. 5.5 g product was collected as pale flakes with 90.6% yield for two steps. 1H NMR: (CDCl3) 2.55 (s, 3H), 3.63 (s, 3H), 7.28 (s, 1H), 7.68 (s, 1H). 13C NMR: (CDCl3): 13.82, 30.05, 110.20, 120.00, 125.58, 125.75, 134.97, 141.83, 153.93. ESI-MS (m/z) calcd (found): 214.0 (215.1) for [M+H]+.

The synthetic route of 5,6-Dichloro-2-methylbenzimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; New York University; Chang, Young-Tae; Wang, Shenliang; US8716491; (2014); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 29518-68-1, 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. 29518-68-1, name is 2-(1H-Benzo[d]imidazol-2-yl)ethanamine belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

(a) 1 -[2-(I H-B enzimidazol-2-y) ethyl] thiourea; {2-(lH-Benzimidazol-2-yl)ethylamine was made as the dihydrochloride salt according to a procedure described by Nicolaou etaJ. Bioorg. Med. Chem., 1998, 6, 1185-1208 and pretreated with DIPEA (2.07 mL, 11.86 mmol) for 5 minutes.} To a suspension of 2-(1H- benzimidazol-2-yl)ethylarnine (1.39 g, 5.93 mmol) in dichloromethane (20 mL) was added benzoyl isothiocyanate (0.88 mL, 6.52 mmol). After 1 h, the reaction mixture was concentrated in vacuo. Ammonia in methanol (7N, 30 mL) was then added and the reaction stirred another 4 h. The excess ammonia and methanol were removed in vacuo and dichloromethane (15 mL) was added. The solid was removed by filtration and the filtrate concentrated in vacuo and purified by flash chromatography (methanol/dichloromethane, 5% thenltheta%) to give the title compound as a solid (1.12 g, 86% yield). 1H NMR (DMSO-de) delta ppm 12.28 (IH), 7.85-7.62 (2H), 7.49 (2H), 7.15-7.10 (2H), 7.05 (IH), 3.86 (2H), 3.04 (2H); MS (ESI) m/z 221 (M+l).

The synthetic route of 2-(1H-Benzo[d]imidazol-2-yl)ethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2007/120098; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 177760-04-2, 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. 177760-04-2, name is Ethyl 2-amino-1-methyl-1H-imidazole-5-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Aminoimidazole (0.700 g, 4.14 mmol) in acetic acid (7.3 mL) was added dropwise to an aqueous solution of sodium nitrite (3.6 mL, 11 M). The solution was stirred at room temperature for 4 h until no more N2 was formed. The reaction mixture was extracted with CH2Cl2 (1 x 20 mL), washed with brine (1 x 20 mL) and a saturated aqueous solution of Na2SO3 (1 x 20 mL). The organic layer was then dried over Na2SO4, filtered and concentrated to afford a crude yellow solid. Purification by flash chromatography using a prepacked 25 g silica column [solvent A: EtOAc; solvent B: hexanes; gradient: 7%A / 93%B (4 CV), 7%A / 93%B ? 60%A / 40%B (10 CV), 60%A / 40%B (2 CV); flow rate: 70 mL/min; monitored at 254 and 280 nm] afforded the nitroimidazole analogue 27 (0.510 g, 2.60 mmol, 63%) as a yellow solid.1H NMR (600 MHz, CDCl3) delta 7.74 (1H, s), 4.40 (2H, q, J = 7.1 Hz), 4.35 (3H, s), 1.41 (3H, t, J = 7.1 Hz).13C NMR (151 MHz, CDCl3) delta 159.08, 147.46, 134.67, 126.29, 61.84, 35.39, 14.18.

The synthetic route of Ethyl 2-amino-1-methyl-1H-imidazole-5-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Winn, Blake A.; Shi, Zhe; Carlson, Graham J.; Wang, Yifan; Nguyen, Benson L.; Kelly, Evan M.; Ross, R. David; Hamel, Ernest; Chaplin, David J.; Trawick, Mary L.; Pinney, Kevin G.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 3; (2017); p. 636 – 641;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 14003-66-8, name is 4-Methyl-5-nitro-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 14003-66-8, Computed Properties of C4H5N3O2

To a stirred suspension of 4(5)-methyl-5(4)-nitroimidazole (5 g, 0.04 mol) in benzaldehyde was added piperidine (3.95 g, 0.04 mol). The mixture was heated to 110 C for 2.5 h. When the reaction was complete and solid started separating, 100 mL ethanol was added to the reaction mixture. The mixture was allowed to cool to room temperature and filtered to obtain a yellow solid which was washed with ethanol and dried to get a pure compound. Yield 6.5 g, 77%; mp: 258-260 C; 1H NMR (DMSO-d6) delta 7.90 (s, 1H, Imid-H), 7.68-7.36 (m, 7H, CH=CH, Ar-H); 13C NMR (DMSO-d6) delta 143.73, 136.33, 136.10, 135.30, 130.93, 129.76, 129.65, 127.54, 114.64; HRMS (FAB), Calcd for C11H9N3O2: 216.0767 (MH+); obsd m/z 216.0769.

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:
Article; Tantravedi, Saritha; Chakraborty, Saibal; Shah, Niti H.; Fishbein, James C.; Hosmane, Ramachandra S.; Bioorganic and Medicinal Chemistry; vol. 21; 17; (2013); p. 4893 – 4903;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem