Tag: M.W=200-300

Synthetic Route of 10040-96-7, 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. 10040-96-7 name is 1-(4-Bromophenyl)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.

22.0g of 1- (4-bromophenyl) -1H-imidazole,27.8g of 10-iodocamphor and 50mL of N, N-dimethylformamide were sequentially added to a three-necked flask equipped with a stirrer, a thermometer and a condensing reflux device.The reaction is carried out at 130 C, and the reaction takes about 4 hours to complete the reaction of one of the raw materials.After cooling, 50 mL of ethyl acetate was added to precipitate the product, and the crude product of camphoryl imidazole iodide was filtered to obtain the target compound by recrystallization from ethanol. The product characterization data is as follows: 80% yield,

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(4-Bromophenyl)imidazole, and friends who are interested can also refer to it.

Reference:
Patent; Nanjing Forestry University; Wang Shifa; Bian Tiancen; Zhao Yuxun; Xu Xu; Yang Yiqin; Gu Wen; (13 pag.)CN110272344; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 10351-75-4, name is 1H-Benzo[d]imidazole-5,6-dicarboxylic 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 10351-75-4, Recommanded Product: 1H-Benzo[d]imidazole-5,6-dicarboxylic acid

General procedure: A mixture containing Eu2O3 (0.2 mmol), MnSO4*H2O (0.3 mmol), H3bidc (0.6 mmol) and water (10 mL) was sealed in a Teflon-lined stainless steel vessel (23 mL), which was heated at 170 C for 4 days and then cooled to room temperature in 2 days. Colorless rhombic crystals of 2 were obtained and picked out, washed with distilled water and dried in air (Yield: 38.17% based on Eu).

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; Sun, Ya-Guang; Zong, Wen-Hui; Xiong, Gang; Guo, Mei-Yan; Ding, Fu; Wang, Shu-Ju; You, Li-Xin; Ren, Bao-Yi; Xu, Zhen-He; Gao, En-Jun; Polyhedron; vol. 83; (2014); p. 68 – 76;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 621-72-7, 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. 621-72-7, name is 2-Benzyl-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Sodium hydride (0.53 g, 6.6 mmol, 60% oil dispresion) was added to the stirred solution of the corresponding azole (3.3 mmol) in anhydrous THF (2 mL) at room temperature. After 15 min, freshly prepared 2-(chloromethyl)-4,5-dihydro-1H-imidazole 2 (0.47 g, 4.0 mmol) was added and the reaction mixture was stirred at ambient temperature for 6 h. The N-alkylation products 3, 5, 7 and 8 were isolated upon quenching the reaction mixture with water (5 mL) followed by extraction with dichloromethane (3 ¡Á 5 mL). The combined organic layers were dried over anhydrous sodium sulfate and evaporated under reduced pressure. The oily residue thus obtained was purified on silica with use of chromatotron (Et3N/MeOH/AcOEt 1:5:100). All products were very polar with Rf values close to 0.05.The N-alkylation reaction of indazoles (1) provided the desired N1 substituted products (3) along with the N2 substituted side product. The latter compounds demonstrated considerably lower Rf than 3 and were not isolated in pure form. The alkylation reactions of benzotriazoles 6a and 6c allowed the isolation of N1 substituted products 7a-b (higher Rf) and N2 isomer 8b (lower Rf). However, in the case of 4-methyl-benzotriazole 6b only the N2 substituted isomer 8a was isolated as a pure product.The products 3, 5, 7 and 8 were then converted into water-soluble hydrochloride salts suitable for biological tests with use of methanolic hydrochloric acid solution or by passing gaseous hydrogen chloride through dichloromethane solution of the corresponding free base.

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

Reference:
Article; Saczewski, Jaroslaw; Hudson, Alan; Scheinin, Mika; Rybczynska, Apolonia; Ma, Daqing; Saczewski, Franciszek; Laird, Shayna; Laurila, Jonne M.; Boblewski, Konrad; Lehmann, Artur; Gu, Jianteng; Watts, Helena; Bioorganic and Medicinal Chemistry; vol. 20; 1; (2012); p. 108 – 116;,
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. 870837-18-6, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, A new synthetic method of this compound is introduced below., Recommanded Product: 870837-18-6

To a solution of intermediate 66 (500 mg, 1.63 mmol) in THF (1 ml) at -75 C was added n-butyl lithium (0.65 ml, 1.63 mmol, 2.5 M in hexanes). The r.m. was stirred for 1 min. at -75 C after which a solution of intermediate 67 (283 mg, 1.31 mmol) in THF (1 ml) was added. The r.m.was then stirred at -75 C for 60 min. and quenched by the addition of a sat. aq. solution of NH4CI (5 ml). The reaction was allowed to warm to r. t. and concentrated under reduced pressure. The residue was purified by flash column chromatography over silica gel (eluent: DCM/MeOH(NH3) from 100/0 to 99/1). The product fractions were collected and concentrated in vacuo, yielding 150 mg of intermediate 68 (21 %).

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; ORTHO-MCNEIL-JANSSEN PHARMACEUTICALS, INC; VAN BRANDT, Sven, Franciscus, Anna; DE CLEYN, Michel, Anna, Jozef; GIJSEN, Henricus, Jacobus, Maria; BERTHELOT, Didier, Jean-Claude; SURKYN, Michel; WO2011/86099; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 305790-48-1, name is 6-Bromo-1-methyl-1H-benzo[d]imidazol-2(3H)-one, 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 305790-48-1, Recommanded Product: 305790-48-1

A mixture of 6-bromo-l-methyl-l,3-dihydro-2H-benzo[d]imidazol-2-one (10.0 g, 44.2 mmol), l, -Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (3.6 g, 4.42 mmol), TEA (9.0 g, 88.5 mmol) in MeOH (200 mL) and DMF (10 mL) was sparged with carbon monoxide for about 10 min, placed under 4 atm carbon monoxide atmosphere, and heated to 130 C for 17 hours. The reaction mixture was cooled down to room temperature, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (PE: EA = 2: 1 ) to give product (7.0 g, 76.9%) as a yellow solid. NMR (400 MHz, DMSO-d6) S 1 1.27 (s, 1 H), 7.77 – 7.53 (m, 2 H), 7.07 (d, J = 8.1 Hz, 1 H), 3.84 (s, 3 H), 3.33 (s, 3 H); LC/MS (ESI, m/z): [M +1]+ = 207.1.

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, 6-Bromo-1-methyl-1H-benzo[d]imidazol-2(3H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KYMERA THERAPEUTICS, INC.; MAINOLFI, Nello; JI, Nan; ZHANG, Yi; WEISS, Matthew M.; (223 pag.)WO2019/60693; (2019); 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. 1450-93-7, name is 1H-imidazol-2-amine sulfate(2:1), A new synthetic method of this compound is introduced below., Formula: C6H12N6O4S

EXAMPLE 2 5-(4-Pyridyl)imidazo[1,2-a]pyrimidine A mixture of 5.29 g of 2-aminoimidazole hemisulfate, 3.28 g of anhydrous sodium acetate and 7.04 g of 3-dimethylamino-1-(4-pyridyl)-2-propen-1-one (prepared according to the procedure of Example 63 in U.S. Pat. No. 4,281,000) in 100 ml of glacial acetic acid was heated under reflux for 16 hours. The procedure of the above Example 1 was followed and the title compound was obtained as pale yellow needles, mp 244-245 C.

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; American Cyanamid Company; US4551530; (1985); A;,
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. 71759-87-0, name is 4-Iodo-1-methyl-1H-imidazole, A new synthetic method of this compound is introduced below., Product Details of 71759-87-0

Methyl (1-N-methyl)imidazole-4-carboxylate. A mixture of 4-iodo-1-methyl-1H-imidazole (500 mg, 2.40 mmol), trans-dichlorobis(triphenylphosphine)palladium(II) (255 mg, 0.30 mmol) and triethylamine (3 mL) in methanol (30 mL) in a pressure vessel was purged with argon for 10 min. The vessel was then pressurized with carbon monoxide to 250 psi and heated at 100 C. for 2 days. After cooling to room temperature, the reaction mixture was filtered through Celite, and concentrated under vacuum. The resultant residue was purified by flash chromatograph on silica gel (5% MeOH in CHCl3) to give title compound. 1H NMR (400 MHz, CDCl3) delta 7.60 (s, 1H), 7.28 (s, 1H), 3.90 (s, 3H), 3.78 (s, 3H).

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; Payne, Linda S.; Tran, Lekhanh O.; Zhuang, Linghang H.; Young, Steven D.; Egbertson, Melissa S.; Wai, John S.; Embrey, Mark W.; Fisher, Thorsten E.; Guare, James P.; Langford, H. Marie; Melamed, Jeffrey Y.; Clark, David L.; US2003/229079; (2003); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 870837-18-6, 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. 870837-18-6, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step B: To a solution of 1 10 mg (0.497 mmol) of 1 -(1 -(4-fluorophenyl)ethyl)piperidin-2- one A6a in THF (2 ml) was added 1 .24 mL of 2M LDA (in THF/Heptane, Acros) at -78 C. The reaction was stirred for 30 min at -78 C, then stirred for 30 min at -20 C, and was re-cooled to -78 C. Added 3-methoxy-4-(4-methyl-1 H-imidazol-1 – yl)benzaldehyde as solid and stirred for 30 min. The mixture was quenched with saturated aqueous NaHCtheta3, extracted with EtOAc (2 times), and washed with brine (2X). The organic phase was dried (MgSO4) and concentrated. The product was purified by a gradient reverse-phase HPLC (CH3CN-H2O with 0.1% formic acid) to furnish 1 10 mg of the product A6. (ES-LCMS, M+1) 438.2. Retention time: 2.94 min.

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, 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SCHERING CORPORATION; WO2009/108766; (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. 1243204-92-3, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C12H11N3O

3-Methoxy-4-(4-methyl-lH-imidazol-l-yl)benzonitrile (3.50 g, 16.4 mmol) was suspended in tetrahydrofuran (31.6 ml) in a nitrogen gas atmosphere at -10C and then, to the resultant suspension were added dropwise a Vitride (TM, manufactured by Sigma- Aldrich Corporation) toluene solution (65 wt%, 3.47 g, 11.2 mmol) using a syringe. After completion of the dropwise addition, the solution was stirred at -10C for one hour, and disappearance of the raw material was confirmed by TLC (silica gel; developing solvent: ethyl acetate; UV detector). Acetone (0.26 mL, 3.58 mmol) was added to the reaction mixture and stirred for 10 minutes, and then the resultant mixture was added dropwise to 5 M hydrochloric acid (18 mL) cooled at 7C while stirring, followed by temperature elevation to room temperature. The resultant solution was added dropwise to a mixture of a 5 M aqueous sodium hydroxide solution (20.4 mL) and toluene (32 mL), which was cooled to 7C in advance, while stirring, and the temperature of the resultant mixture was elevated to room temperature. The lower layer (aqueous layer) was separated from the organic layer, the aqueous layer was further extracted with toluene (18 mL) and the toluene layer and the above organic layer were combined. The combined organic layer was washed with a 10% aqueous sodium chloride solution (18 mL x 4) and then filtered through a Celite (1 g) pad, and the resultant filtrate was concentrated under a reduced pressure at a water bath temperature of 50C. The residue was further subjected to azeotropic distillation with toluene under a reduced pressure to obtain 3.70 g of a crude product containing a title compound.The obtained crude product was dissolved in a mixture of toluene (3.5 mL) and acetone (7 mL) at 60C, and n-heptane (15.8 mL) was slowly added dropwise to the resultant solution while stirring so that the internal temperature was maintained at 50C or higher. After completion of the dropwise addition, the solution was subjected to crystallization (seed crystal: lotNo. A6103102) at 53C, the water bath was removed and the slurry was gradually cooled to room temperature and stirred overnight. The resultant slurry was further cooled to 7C and stirred for 9 hours and 30 minutes, and then the solids were collected by filtration and washed with an acetone/n-heptane (1/3) mixture which was cooled to 7C in advance, and dried under a reduced pressure at 45 to 50C for 1.5 hours to obtain 2.64 g of a title compound (yield: 74.4%). The quantitative determination by HPLC showed that the loss of the compound into the mother liquor was 0.435 g (12.3%).The above-obtained title compound (2.64 g) and the mother liquor (containing 0.435 g of the compound) were mixed together, the mixture was concentrated, the concentrate was dissolved in a mixture of toluene (3 mL), acetone (6 mL), and tert-butyl methyl ether (18 mL), which was warmed at 48C, and then the resultant solution was cooled to 42C to perform a crystallization. The resultant slurry was gradually cooled to room temperature and stirred overnight. To the slurry was further added dropwise tert-butyl methyl ether (9 mL), and then the resultant mixture was stirred for one hour, cooled to 8C and stirred for one hour, followed by stirring at 4C overnight (17 hours). The solids were collected by filtration and dried under a reduced pressure to obtain 1.97 g of a title compound (yield: 64.6%). The quantitative determination by HPLC showed that the loss of the compound into the mother liquor was 0.674 g (22%).

According to the analysis of related databases, 1243204-92-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Eisai R&D Management CO., LTD.; YOSHIKAWA, Seiji; KAYANO, Akio; WO2011/37244; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1231930-33-8, name is 6-Bromo-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. name: 6-Bromo-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole

A suspension of 6-bromo-4-fluoro-2-methyl-1-(propan-2-yl)-1H-benzimidazole (Int-46) (90 g, 331.95 mmol), bis(pinacolato)diboron (126 g, 498 mmol), AcOK (80 g, 815.15 mmol), tricyclohexylphosphine (14 g, 49.8 mmol), and Pd(OAc)2 (7.45 g, 33.2 mmol) in DMSO (1.0 L) was sparged with N2 and then stirred at 100 C. for 16 h. TLC analysis (1:1 petroleum ether/EtOAc) showed complete consumption of the starting material. The black suspension was poured into H2O (3.0 L) and extracted with EtOAc (2*3 L). The combined organic phases were washed with brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by flash chromatography (Biotage, 1.0 kg, 0-40% EtOAc/petroleum ether) to provide 4-fluoro-2-methyl-1-(propan-2-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzimidazole (A-1) (77 g, 73% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3) delta 7.69 (s, 1H), 7.33 (d, J=10.8 Hz, 1H), 4.77-4.61 (m, 1H), 2.65 (s, 3H), 1.65 (d, J=7.0 Hz, 6H), 1.36 (s, 12H); m/z (ESI+) for (C17H24BFN2O2), 319.2 (M+H)+.

The synthetic route of 1231930-33-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; Chen, Ping; Cho-Schultz, Sujin; Deal, Judith Gail; Gallego, Gary Michael; Jalaie, Mehran; Kania, Robert Steven; Nair, Sajiv Krishnan; Ninkovic, Sacha; Orr, Suvi Tuula Marjukka; Palmer, Cynthia Louise; (169 pag.)US2019/330196; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem