Month: May 2021

Reference of 253453-91-7, These common heterocyclic compound, 253453-91-7, name is 2-Chloro-1-methyl-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.

General procedure: To a solution of 2-chloro-1-methyl-1H-imidazole (92.8 g, 796 mmol) (see the Supporting Information for the synthesis) in anhydrous THF (1.8 L) was added dropwise a solution of t-BuLi (336 mL, 2.5 M, 840 mmol) in hexane at -60 C with stirring over 2 h. After the addition, a solution of (SS)-4 (221.6 g, 799 mmol) in anhydrous THF (1.0 L) was added dropwise to the above solution over 1 h at the same temperature. The resulting mixture was warmed from -60 C to r.t. with stirring overnight. TLC (PE-EtOAc, 1:1) showed the expected spot (Rf = 0.3). The mixture was poured into sat. aq NH4Cl (1 L) and extracted with EtOAc (3 × 0.8 L). The organic layers were combined, washed with brine (1 L), dried (Na2SO4), and concentrated. The crude product was purified by flash column chromatography on silica gel (PE-EtOAc, 10:1 ? 2:1) to give the title compound; yield: 189.9 g (60%); yellow solid; Rf = 0.3 (EtOAc-PE, 1:1).

The synthetic route of 253453-91-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Yantao; Goldberg, Frederick W.; Xiong, Jian; Wang, Shujun; Synthesis; vol. 47; 5; (2015); p. 679 – 691;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 914306-50-6, name is 1-(2,6-Diisopropylphenyl)-2-phenyl-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. SDS of cas: 914306-50-6

1-(2,6-diisopropylphenyl)-2-phenyl-1H-imidazole (2) (14.77 g, 48.5 mmol) was dissolved in DMF (200 ml) and NB S (9.50 g, 53.4 mmol) was added and the mixture was stirred at room temperature for 48 hours. More NBS (8.63 g, 48.5 mmol) was added and the reaction was stirred in a 70 C. oil bath for another 24 hours. Solvents were removed by kugelrohr and the residue was partitioned between EtOAc and water, filtering through a frit to remove black insoluble materials. The aqueous layer was extracted twice more with EtOAc, the organics were washed with water and brine, dried and purified by column chromatography to yield 3 as a colorless solid, 18.27 (81%).

The synthetic route of 1-(2,6-Diisopropylphenyl)-2-phenyl-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Universal Display Corporation; Szigethy, Geza; (140 pag.)US2018/319830; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 865998-46-5, name is Ethyl 5-nitro-1H-imidazole-2-carboxylate, 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 865998-46-5, Computed Properties of C6H7N3O4

Example 33A Ethyl 1-(2,6-dichlorobenzyl)-4-nitro-1H-imidazole-2-carboxylate 1000 mg (5.4 mmol) of ethyl 4-nitro-1H-imidazole-2-carboxylate together with 1426 mg (5.94 mmol) of 2,6-dichlorobenzyl bromide were dissolved in 37 ml of DMF, and 2112 mg (6.48 mmol) of cesium carbonate were added. The mixture was stirred at 75 C. for 4 h. After cooling to RT, the mixture was added to 100 ml of ice-water. The precipitated product was filtered off and washed with water. The beige solid was dried under high vacuum. This gave 1500 mg (81% of theory) of the target compound. LC/MS [Method 1]: Rt=2.05 min; MS [ESIpos]: m/z=344 and 346 (M+H)+ 1H-NMR (400 MHz, DMSO-d6): delta=1.35 (t, 3H), 4.41 (q, 2H), 5.96 (s, 2H), 7.53 (dd, 1H), 7.59-7.64 (m, 2H), 7.96 (s, 1H).

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, Ethyl 5-nitro-1H-imidazole-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; Furstner, Chantal; Keldenich, Joerg; Delbeck, Martina; Kolkhof, Peter; Kretschmer, Axel; Pluschkell, Ingo; Pook, Elisabeth; Schmeck, Carsten; Trubel, Hubert; US2013/190330; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 109012-23-9, 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. 109012-23-9 name is Ethyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate, 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.

Ethyl 1-methyl-4-nitroimidazole-2-carboxylate17 (6, 613 mg, 3.1 mmol) was hydrogenated over 5% palladium on charcoal in ethanol. The resulting amino compound was dried thoroughly under vacuum to remove traces of ethanol. It was then dissolved in dichloromethane (20.0 mL) and the solution was cooled to 0-5 C. To the cold solution was added triethylamine (0.5 mL, 3.7 mmol) followed by benzoyl chloride (0.4 mL, 3.4 mmol). The reaction mixture was allowed to attain room temperature and then stirred for 12 h. Upon completion, the reaction was quenched with water (15.0 mL) and stirred for 15 min. The organic layer was separated and aqueous layer was washed with dichloromethane (2 × 10 mL). Combined organic layers were dried over sodium sulfate and evaporated to obtain a yellow oil. The crude product was purified by column chromatography using silica gel and 2% methanol in chloroform as the eluent system to obtain 7 as a yellow solid (808 mg, 96%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Article; Satam, Vijay; Babu, Balaji; Chavda, Sameer; Savagian, Mia; Sjoholm, Robert; Tzou, Samuel; Liu, Yang; Kiakos, Konstantinos; Lin, Shicai; David Wilson; Hartley, John A.; Lee, Moses; Bioorganic and Medicinal Chemistry; vol. 20; 2; (2012); p. 693 – 701;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 78597-27-0, A common heterocyclic compound, 78597-27-0, name is 6-Iodo-1H-benzo[d]imidazole, molecular formula is C7H5IN2, 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.

b) 5-((Trimethylsilyl)ethynyl)- 1 H-benzo [djimidazoleA solution of of the compound of Intermediate Example 12(a) (0.7 g, 2.56 mmol) inDMF-Et3N (1:1; 10 ml) was degassed by N2 bubbling for 15 mm. Pd(dppf)Cl2 (0.11g,. 0.14. mmol, 0.05 eq), copper(]) iodide (0.054g, 0.25 mmol, 0.1 eq) and ethynyltrimethylsilane.(0.3 g, 3.15 mmol; 1.1 eq) were added sequentially and the mixture was stirred for 12 h at RT. The mixture was quenched and extracted as in Intermediate Example 1. The solvent was distilled off and the crude residue was recrystallized fromhexane to afford the title product in 57 % yield (0.35 g). LC-MS (ESI): Calculated mass:214.09;Observed mass: 215.5 jM+H] + (rt: 0.22 mm).

The synthetic route of 78597-27-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ORION CORPORATION; RAJAGOPALAN, Srinivasan; APPUKUTTAN, Prasad; NARASINGAPURAM ARUMUGAM, Karthikeyan; UJJINAMATADA, Ravi Kotrabasaiah; GEORGE, Shyla; LINNANEN, Tero; WO2014/162039; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 20033-99-2, A common heterocyclic compound, 20033-99-2, name is 2-(Hydroxymethyl)-5-methoxybenzimidazole, molecular formula is C9H10N2O2, 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.

Thionyl chloride (27.5 mmol, 2 mL) was added slowly to a solution of 5-methoxy-1H-benzimidazole-2-yl)-methanol) 26 (0.58 g, 3.31 mmol) in dichloromethane (10 mL) at 10 C, the mixture was stirred until no presence of the starting material. The solvent was then evaporated, and the residue was triturated with DCM, and suction filtered, then was washed with dichloromethane and ether. Yield 89% which 34 was recovered as a green powder.

The synthetic route of 20033-99-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Alasmary, Fatmah A.S.; Snelling, Anna M.; Zain, Mohammed E.; Alafeefy, Ahmed M.; Awaad, Amani S.; Karodia, Nazira; Molecules; vol. 20; 8; (2015); p. 15206 – 15223;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 29518-68-1, name is 2-(1H-Benzo[d]imidazol-2-yl)ethanamine, 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 29518-68-1, Recommanded Product: 2-(1H-Benzo[d]imidazol-2-yl)ethanamine

Carbonyldiimidazole (23.4 g; 0.145 mol) was added to a solution of glutaric acid (8 g; 0.06 mol) in anhydrous tetrahydrofuran (500 ml) and stirred for 2 hours. Then benzimidazolyl ethylamine (21.6 g; 0.133 mol) was added to the reaction mixture. The resulting solution was stirred for 3 hours and allowed to stand at room temperature. The residue of the product was separated, washed with water, and dried. The yield was 21 g (82.9%). Rf 0.21 (2). M.p. 170-170.5 C. [M]+419. 1H-NMR (DMSO): delta, m.d.: 1.61-1.76 (m, 2H, CH2), 1.95-2.07 (t, 2H, CH2), 2.9-3.0 (t, 4H, 2CH2), 3.45-3.55 (quint, 4H, 2CH2), 7.06-7.14 (m, 4H, Ar), 7.39-7.54 (m, 4H, Ar), 7.98-8.08 (t, 2H, Ar), 11.6-12.7 (s, 2H, NH). HPLC under condition B: an individual peak at a retention time of 26.6 min.

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; OBSCHESTVO S OGRANICHENNOI OTVETSTVENNOSTIYU “PHARMENTERPRISES”; NEBOLSIN, Vladimir Evgenievich; KROMOVA, Tatyana Alexandrovna; ZHELTUKHINA, Galina Alexandrovna; (19 pag.)US2016/31858; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 115576-91-5, These common heterocyclic compound, 115576-91-5, name is (1-Methyl-1H-benzo[d]imidazol-5-yl)methanol, 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.

Example 11C : [1-METHYLBENZIMIDAZOLE-5-CARBOXALDEHYDE] A solution of 5-hydroxymethyl-1-methylbenzimidazole (0.8 g, 4 mmol) in acetone (40 [ML)] was treated with [MN02] (4 g) and the mixture was stirred for 3 days. The solid was filtered off and the solvent removed under reduced pressure to give 0.63 g of product. [COHGN2O] Mass (calculated): [160]; (found): [M+H+] = 161. NMR (400 [MHZ, DMSO-D6)] : 3.95 (3H, s, NCH3) ; 7.8 [(1H,] d, J = 8 Hz, aryl-H); 7.9 [(1H,] dd, [J =] 1 and 8 Hz, aryl-H); 8.3 [(1H,] d, J= 1 Hz, aryl-H); 8.45 [(1H,] s, imidazole-H); 10.1 [(1H,] s, CHO).

The synthetic route of 115576-91-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN, INC.; WO2003/99814; (2003); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 40507-59-3, 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. 40507-59-3, name is 4-Nitro-1H-imidazole-5-carboxylic acid belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

JDF03 was prepared from nitroimidazole carboxylic acid by treatment with SOCl2.

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, 4-Nitro-1H-imidazole-5-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Jean-Claude, Bertrand; US2012/283280; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 39811-07-9, 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. 39811-07-9, name is (5-Fluoro-1H-benzo[d]imidazol-2-yl)methanol, This compound has unique chemical properties. The synthetic route is as follows.

Thionyl chloride (27.5 mmol, 2 mL) was added slowly to a solution of 5-flouro-1H-benzimidazole-2-yl)-methanol) (FAS27) (0.55 g, 3.31 mmol) in dichloromethane (10 mL) at 10 C, the mixture was stirred until no presence of the starting material. The solvent was then evaporated, and the residue was triturated with dichloromethane, suction filtered, washed with dichloromethane and ether. 2-(Chloromethyl)- 5-flouro-1H-benzimidazole 45 was recovered as a brown powder in Yield 80%.

The chemical industry reduces the impact on the environment during synthesis (5-Fluoro-1H-benzo[d]imidazol-2-yl)methanol. I believe this compound will play a more active role in future production and life.

Reference:
Article; Alasmary, Fatmah A.S.; Snelling, Anna M.; Zain, Mohammed E.; Alafeefy, Ahmed M.; Awaad, Amani S.; Karodia, Nazira; Molecules; vol. 20; 8; (2015); p. 15206 – 15223;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem