Month: May 2021

Synthetic Route of 53484-16-5, 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 53484-16-5 as follows.

A mixture of Pd2(dba)3 (0.01 mmol) and Xantphos (0.01 mmol) in 1 ,4-dioxane (1 mE) was sonicated and added undernitrogen to a mixture of 6-bromo-1-methyl-benzimidazole (0.45 mmol), 2,3-dihydro-1 ,4-benzodioxin-6-amine (0.58 mmol) and Cs2CO3 (0.62 mmol) in 1,4-dioxane (2 mE). The mixture was stirred at 1100 C. for 12 h. The mixture was diluted (DCM), washed (H20), dried (phase separator andconcentrated. The residue was purified by prep HPEC toyield the desired product (Compound B).

According to the analysis of related databases, 53484-16-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GALAPAGOS NV; Menet, Christel Jeanne Marie; Mammoliti, Oscar; Blanc, Javier; Orsulic, Mislav; Roscic, Maja; (81 pag.)US9440929; (2016); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 57667-50-2, name is 1-Propyl-1H-benzo[d]imidazol-2-amine, 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 57667-50-2, name: 1-Propyl-1H-benzo[d]imidazol-2-amine

General procedure: 6.1.2. Method BTo a solution of 1-(un)substituted-2-aminobenzimidazole (0.01 mol) in dry acetonitrile (50 ml) was added anhydrous potassium carbonate (2.7 g, 0.02 mol) and tetrabutyl ammonium bromide (TBAB) (0.9 g, 0.003 mol) and 0.02 mol of the halogen organic reagent was dropped by cooling. The mixture was stirred for 2-5 h vigorously at 25 C and monitored by TLC over the reaction period. After completion of the reaction, the mixture was filtered to separate the solid K2CO3, and the organic solvent was evaporated. The residue was then crystallized from appropriate solvent to give products 4-8.

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; Mavrova, Anelia Ts.; Wesselinova, Diana; Vassilev, Nikolay; Tsenov, Jordan A.; European Journal of Medicinal Chemistry; vol. 46; 8; (2011); p. 3362 – 3367;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 1003-91-4, 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. 1003-91-4, name is 2,4,5-Tribromo-1-methylimidazole, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: [M(PPh3)4] (1.0 equiv.) was added as a solid to a toluene solution (15mL) of 1 or 2 (1.0 equiv.) in a Schlenk flask and was stirred overnight at room temperature. The solvent was removed under the vacuum. The resulted yellow residue was dissolved in DCM (2mL) and was precipitated by addition of n-pentane (15mL), filtered and dried in vacuum to afford the product as yellow powder.

The chemical industry reduces the impact on the environment during synthesis 2,4,5-Tribromo-1-methylimidazole. I believe this compound will play a more active role in future production and life.

Reference:
Article; Avinash, Iruthayaraj; Gupta, Vivek; Karthik, Vedhagiri; Anantharaman, Ganapathi; Journal of Organometallic Chemistry; vol. 851; (2017); p. 104 – 114;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 570-22-9,Some common heterocyclic compound, 570-22-9, name is 1H-Imidazole-4,5-dicarboxylic acid, molecular formula is C5H4N2O4, 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.

To a dry round-bottom flask was added 1.0 g of imidazole-4,5-dicarboxylic acid (10, 1 mmol) and 10 mL of toluene. To this stirred suspension were added 3.0 mL of thionyl chloride (6.5 mmol) and 0.250 mL of DMF (catalytic). The resulting mixture was refluxed for 16 h. After the mixture was cooled in ice bath, the solid product was collected by vacuum filtration, washed with two 20 mL portions of toluene, and dried under vacuum to yield 0.95 g of crude 11 (Yield: 95%) as a yellow solid. This product was used further without characterization.

The synthetic route of 570-22-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Saudi, Milind; Zmurko, Joanna; Kaptein, Suzanne; Rozenski, Jef; Neyts, Johan; Van Aerschot, Arthur; European Journal of Medicinal Chemistry; vol. 87; (2014); p. 529 – 539;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 288-32-4,Some common heterocyclic compound, 288-32-4, name is 1H-Imidazole, molecular formula is C3H4N2, 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: Arylhalide (1.0 mM), nitrogen-containing heterocycle (1.2 mM), KOH (2 mM), and the catalyst (0.75 M%) were stirred in dimethyl sulfoxide (DMSO) (4 mL) at 110 C for 10 h. After completion of the reaction, the mixture was cooled to room temperature, diluted with ethyl acetate (10 mL) and filtered. The filtrate was concentrated and the residue was purified by column chromatography on silica gel using hexane/ethyl acetate(70 : 30) as eluent to afford the desired product. The products have been characterized by 1H NMR spectroscopy.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1H-Imidazole, its application will become more common.

Reference:
Article; Anitha, Panneerselvam; Manikandan, Rajendran; Viswanathamurthi, Periasamy; Journal of Coordination Chemistry; vol. 68; 19; (2015); p. 3537 – 3550;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 7189-69-7,Some common heterocyclic compound, 7189-69-7, name is 1,1′-Sulfonyldiimidazole, molecular formula is C6H6N4O2S, 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.

A 20-mL vial was charged with N-(4-methoxybenzyl)-6-methylpyrimidin-4-amine (Preparation 7i, 500 mg, 2.181 mmol) and l,r-sulfonylbis(lH-imidazole) (864 mg, 4.36 mmol) then purged with nitrogen. 2-Methyltetrahydrofuran (10.0 mL) and a solution of lithium hexamethyldisilazide in THF (1.0 M, 4.27 mL, 4.27 mmol) were added via syringe to the stirred reaction mixture. The vial was sealed with a Teflon coated cap and the reaction was warmed to 90 C and stirred vigorously. After 1 h, the red reaction mixture was allowed to cool to ambient temperature. The reaction mixture was diluted with water (25 mL) and EtOAc (25 mL). The layers were separated and the aqueous layer extracted with additional EtOAc (2 x 25 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure and purified by flash column chromatography (100-g silica gel Biotage column, eluent: gradient, 20 to 80% 3:1 EtOAc/EtOH in heptane with DCM as a 10% additive) to afford N-(4-methoxybenzyl)-N-(6-methylpyrimidin-4-yl)-1H-imidazole-1-sulfonamide (0.64 g, 1.78mmol, 82 % yield) as a reddish oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,1′-Sulfonyldiimidazole, its application will become more common.

Reference:
Patent; USA Anjin Corporation; M .weisi; B .C.miergelamu; T .dining; J .siteerwogen; A .gusiman-peileisi; A .beiqiao; I .E.makesi; (177 pag.)CN107531705; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 28890-99-5, 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. 28890-99-5, name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 104.20 g (10 mmol) 2,8-diiododibenzofuran, 13.0 g (40.0 mmol) caesium carbonate, 1 ,90 g (1.00 mmol) copper(l) iodide and 2.30 g (20.0 mmol) L-proline are added to 4.56 g (22.0 mmol) mmol) 5H-benzimidazo[1 ,2-a]benzimidazole in 100 ml dimethylsulfoxide (DMSO) under nitrogen. The reaction mixture is stirred for 24 h at 100 C, filtered and washed with dichloromethane. The organic phase is dried with magnesium sulfate and the solvent is distilled off. The product is crystallized form ether. Yield 4.7 g (81 %)1 H NMR (400 MHz, THF-d8): delta 8.73 (d, J= 1.2 Hz, 2H), 8.14 (d, J= 2.3 Hz, J=8.8 Hz, 2H), 7.96-8.02 (m, 4H), 7.92 (d, J=8.8 Hz, 2H), 7.70-7.73 (m, 2H), 7.62 (d, J= 7.1 Hz, 2H), 7.25- 7.40 (m, 8 H).

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, 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BASF SE; SCHAeFER, Thomas; FIGUEIRA DUARTE, Teresa, Marina; SCHILDKNECHT, Christian; LANGER, Nicolle; HEINEMEYER, Ute; WOLLEB, Heinz; WATANABE, Soichi; LENNARTZ, Christian; WAGENBLAST, Gerhard; WOLLEB, Annemarie; BARDON, Kristina; BENEDITO, Flavio, Luiz; WO2012/130709; (2012); 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. 583-42-6, name is 5-Fluoro-1H-benzo[d]imidazole-2(3H)-thione, A new synthetic method of this compound is introduced below., Quality Control of 5-Fluoro-1H-benzo[d]imidazole-2(3H)-thione

A suspension of 5-fluoro-lJ./-benzoimidazole-2-thiol (168 mg, 1 mmol), 5-bromo-pentanoic acid ethyl ester (188 mg, 0.9 mmol, 145 ILL.) and K2CO3 (276 mg, 2 mmol) inacetone (2 ml) is refluxed for 3 h. It is cooled down and filtered over a short plug ofsilica gel and rinsed with AcOEt. The solvent is removed in vacua. The crude ispurified by flash chromatography on silica-gel (AcOEt / heptane, 1 :2), yielding the titlecompound (190 mg) in 64% as a brown oil: fo = 1.87 min (LC-2), ESI-MS (pos.): m/z297.28 [M+H]+, ESI-MS (neg.): m/z 295.30 [M-H]+; .H-NMR (CDC13): 5 (ppm) 1.25(t, 3H, CH3), 1.79 (br. t, 4H), 2.36 (br. t, 2H, CH2CO), 3.28 (br. t, 2H, SCH2), 4.14 (q,2H, CHaO), 6.93 (dt, lHarom), 7.20 (dd, lHarom), 7.41 (dd, lHarom).

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; ACTELION PHARMACEUTICALS LTD; WO2006/21418; (2006); 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. 934-22-5, name is 6-Aminobenzimidazole, A new synthetic method of this compound is introduced below., COA of Formula: C7H7N3

Compound 467: 1 -(1 H-benzo[d]imidazol-6-yl)-5-(2,3-difluorophenyl)-3-hydroxy-4- methyl-1 H-pyrrol-2(5H)-one; 1 H-Benzoimidazol-5-ylamine (1 mmol) was dissolved in 5ml_ of dry EtOH and 2,3- difluorobenzaldehyd (1 mmol) were added. The solution was stirred overnight and after that 2- oxal-propionsaure diethylester (1 mmol) was added and the solution was stirred for 2Oh at 500C. After that the solvent was evaporated and remaining oil was subjected to a flash chromatography device and purified by means of a CHC^/MeOH gradient. The purified carboxylic acid ethyl ester derivative was suspended in 1OmL of a 10% aqueous solution of HCI and kept for 3h at reflux. The resulting precipitate was filtered off and dried. Yield: 0.15Og (46 %);1H-NMR (400 MHz, CD3OD), 1.78 (s, 3H, CH3), 6.06 (s, 1 H, CH-N), 6.94 – 7.17 (m, 3H, aro), 7.74 (s, 2H, benzimid), 8.08 (s, 1 H, benzimid), 9.27 (s, 1 H, benzimid), MS m/z 342.1 (M+H)+, HPLC (254 nm): purity 100 %molecular weight (g/mol): 341.3 Ki hQC (nM): 1 1.6

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; PROBIODRUG AG; WO2008/55945; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 401567-00-8, The chemical industry reduces the impact on the environment during synthesis 401567-00-8, name is 2-Chloro-1H-benzo[d]imidazole-5-carbonitrile, I believe this compound will play a more active role in future production and life.

4.1.18. 2-Chloro-5-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)benzimidazole and 2-chloro-6-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)benzimidazole (17) To a solution of 2-chloro-5-cyanobenzimidazole (1.4 g,8.1 mmol) and triethylamine (3.4 mL, 24 mmol) in anhydrousDMF (30 mL) was added 2-(trimethylsilyl)ethoxymethyl chloride(2.2 mL, 12 mmol), and the mixture was stirred at room tempera-ture for 2.5 h. Triethylamine (1.7 mL, 16 mmol) was further added,and stirring was continued overnight. The reaction was thenquenched by addition of water, and the resulting mixture wasextracted with AcOEt. The combined organic layer was washedwith 2 N aq HCl and brine, dried over Na2SO4, and concentratedunder reduced pressure. The residue was puried by silica gel col-umn chromatography (n-hexane/AcOEt = 3:1) to afford the product17 (2.2 g, 87%, 1:1 regioisomeric mixture) as a white solid.1H NMR (500 MHz, CDCl3) d 8.03 (s, 1/2H), 7.81 (d, J = 1.1 Hz,1/2H), 7.77 (d, J = 8.6 Hz, 1/2H), 7.61-7.55 (m, 3/2H), 5.59 (s, 2H),3.60-3.55 (m, 2H), 0.95-0.89 (m, 2H), 0.03 (s, 9H); 13C NMR(125 MHz, CDCl3) d 144.6, 144.1, 143.3, 141.3, 137.6, 134.5,127.2, 126.9, 124.3, 120.5, 119.2, 115.0, 111.3, 73.6, 73.5, 67.2,17.7, 1.5; MS (FAB) m/z 308 (M+H)+.

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, 2-Chloro-1H-benzo[d]imidazole-5-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Okazaki, Shogo; Noguchi-Yachide, Tomomi; Sakai, Taki; Ishikawa, Minoru; Makishima, Makoto; Hashimoto, Yuichi; Yamaguchi, Takao; Bioorganic and Medicinal Chemistry; vol. 24; 21; (2016); p. 5258 – 5269;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem