Tag: M.W=100-200

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. 75370-65-9, name is 4-Amino-1H-benzo[d]imidazol-2(3H)-one, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 4-Amino-1H-benzo[d]imidazol-2(3H)-one

Preparation of 1-(4-(trifluoromethyl)benzyl)-3-(2,3-dihydro-2-oxo-1H-benzo[d]imidazol-4-yl)urea Commercially available 4-trifluoromethylbenzylamine (0.5 ml, 3.5 mmol) was dissolved in 20 ml of AcOEt and at OC triphosgene (1 g, 3.5 mmol) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 5 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (5 ml) of compound 1a (350mg, 2.33mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt 9.5 / MeOH 0.5). The solvent was evaporated and the crude was dissolved in AcOEt (30ml) and washed with water (1 X 20ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 290mg of a white solid. Yield = 36% 1HNMR (DMSO, 400 MHz) delta 4.40 (2H, d, J = 6 Hz), 6.62 (1H, d, J = 7.2 Hz), 6.84 (2H, m), 6.96 (1H, d, J = 8 Hz), 7.54 (2H, d, J = 8 Hz), 7.70 (2H, d, J = 8.4 Hz), 8.30 (1H, s), 9.99 (1H, bs), 10.60 (1H, bs); [M+1] 351.1 (C16H13F3N4O2 requires 350.3).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 75370-65-9.

Reference:
Patent; Pharmeste S.r.l.; EP2377850; (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. 7189-69-7, name is 1,1′-Sulfonyldiimidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 1,1′-Sulfonyldiimidazole

General procedure: A solution of 500 mg (4.46 mmol) of 2-fluorophenol 1.769 g (8.92 mmol) of 1,1?-sulfonyldiimidazole in 15 mL of tetrahydrofuran was treated with 727 mg (2.23 mmol) of cesium carbonate. The reaction was stirred for 12 h, concentrated, and the residue was partitioned between the ethyl acetate and water (10 mL each). The organic layer was washed sequentially with saturated ammonium chloride solution and brine. After drying over the anhydrous sodium sulfate, the organic layer was concentrated and chromatographed on silica with 1:5 ethyl acetate / hexane as the eluant to afford 880 mg (90%) of 11bas a clear oil:

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:
Article; Yang, Baocheng; Sun, Zhexun; Liu, Changzhi; Cui, Yan; Guo, Zhilei; Ren, Yuwei; Lu, Zhijian; Knapp, Spencer; Tetrahedron Letters; vol. 55; 49; (2014); p. 6658 – 6661;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 45676-04-8, A common heterocyclic compound, 45676-04-8, name is 1-tert-Butylimidazole, molecular formula is C7H12N2, 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.

1.2.7) 3-tert-Butyl-1-[(tert-butyl(methyl)phosphinooxy)methyl]imidazolium tosylate 15 In a Schlenk tube with pressure release valve, 1.00 g (3.3 mmol) of tert-butyl(methyl)-(tosylmethyl)phosphine oxide (14) and 0.45 g (3.6 mmol) of N-tert-butylimidazole (1) were stirred in 0.7 ml of toluene at 105 C. for 72 hours. The red-brown, viscous oil was precipitated from 10 ml of hexane in an ultrasound bath.

The synthetic route of 45676-04-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF SE; US2010/317866; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 39070-14-9,Some common heterocyclic compound, 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, molecular formula is C5H7N3O3, 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.

2,6-Dichloro-4-nitro-phenol (243 mg, 1.17 mmol) is dissolved in methylene chloride (2 mL). To the solution is added (3-methyl-2-nitro-3H-imidazol-4-yl)-niethanol (115 mg, 0.732 mmol) and triphenylphosphine (211 mg, 0.805 mmol). The mixture is stirred at roomtemperature until a solution is achieved. The solution is then cooled in an ice bath and treated with diisopropyl azodicarboxylate, DIAD (158 mu,, 0.805 mmol). After 1 hour the ice bath is removed and the mixture is stirred overnight at room temperature. Crude product is purified on a silica gel column to isolate the product mixed with triphenylphosphine oxide. The solids are triturated with t-butyl methyl ether to remove the triphenylphosphine oxide to afford 5-(2,6- dichloro-4-nitro-phenoxymethyl)- 1 -methyl-2-nitro- IH-imidazole. MS (ESI+) for C11H8Cl2N4O5 m/z 347.0 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, its application will become more common.

Reference:
Patent; GENCIA CORPORATION; KHAN, Shaharyar; (80 pag.)WO2018/129258; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 172499-76-2, name is Ethyl 3-(1H-imidazol-2-yl)propanoate, 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 172499-76-2, Safety of Ethyl 3-(1H-imidazol-2-yl)propanoate

General procedure: A suspension of tBuOK (1.1 equiv. or 2.2 equiv.) and the imidazole derivative (1.0 equiv.) in DMF (6 mL/mmol) was stirred at rt for 1 h. The reaction mixture was treated with the corresponding alkyl bromide or alkyl mesylate (1.3 equiv. or 2.0 equiv.) and the temperature was raised up to 60 C and stirred at this temperature for 72 h. The solution was then diluted with EtOAc (20 mL/mmol) and washed three times with brine and H2O. The organic layers were dried over MgSO4, filtered, and concentrated. The crude product was purified by CC.

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 3-(1H-imidazol-2-yl)propanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kerscher-Hack, Silke; Renukappa-Gutke, Thejavathi; Hoefner, Georg; Wanner, Klaus T.; European Journal of Medicinal Chemistry; vol. 124; (2016); p. 852 – 880;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 7152-24-1, name is 2-(Methylthio)benzimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 7152-24-1

General procedure: A mixture of KOH and 2-methylmercaptobenzimidazole was stirred in DMF at room temperature for 1 h. The dibromo compound was added to the above reaction mixture was allowed to stir continuously at room temperature for 24 h. The reaction was quenched by adding water. The resulting powder was collected by filtration and was dried.

The synthetic route of 7152-24-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Rajakannu, Palanisamy; Elumalai, Palani; Mobin, Shaikh M.; Lu, Kuang-Lieh; Sathiyendiran, Malaichamy; Journal of Organometallic Chemistry; vol. 743; (2013); p. 17 – 23;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 16681-59-7, 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 16681-59-7 as follows.

2-Bromo-l -methyl- 1H- imidazole (47 mu-, 0.48 mmol) was dissolved in diethyl ether (2 mL) and cooled to -75C under argon. Butyl lithium (2.5 M in hexanes: 192 (uL, 0.48 mmol) was added dropwise and the mixture stirred at -75C for 1 hour. A solution of (R)-l-(4- fluorophenyl)-6-((4-(trifluoromemyl)phenyl)sulfonyl)-4,4a,5,6,7,8-hexahydro-lH-pyra.zolo[3,4- g]isoqumoline~4a~carbaldehyde (252 mg, 0.5 mmol) in diethyl ether (2 mL) was added dropwise The reaction mixture was stirred for 16 hours whilst warming slowly to room temperature. The reaction mixture was cooled and treated with water (10 mL) and the phases separated. The organic phase was extracted with further diethyl ether (x2) followed by diehloromethane (x2). The combined organic phases were dried over sodium sulfate, the solids were removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (gradient: 17.5 to 25% acetone in cyelohexane) to afford (R)-(l-(4-fluorophenyl)-6-((4-(Mflu^ pyrazolo[3,4-g]isQquinoim-4a-yi)(l as a white powder (82 mg) LCMS (Method A, ESI): RT 2.74 min, m+H = 588.1

According to the analysis of related databases, 16681-59-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CORCEPT THERAPEUTICS, INC.; HUNT, Hazel; JOHNSON, Tony; RAY, Nicholas; WALTERS, Iain; WO2013/177559; (2013); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 98873-55-3, name is 2-(1H-Imidazol-1-yl)acetonitrile, molecular formula is C5H5N3, 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. Computed Properties of C5H5N3

General procedure: A solution of aryl acetonitrile 2 (50 mg), and triethylamine (1.1 equiv.) in dimethylformamide dimethyl acetal (0.5 mL, 3.76 mmol) was heated in a microwave reactor at 120 C for 20 minutes. The mixture was cooled to RT, and solvents were then evaporated. To the resulting crude product 3 was added hydrazine mono-hydrobromide (3.0 equiv.), 200 proof EtOH (1.0 mL), and H2O (0.3 mL). The mixture was heated in a microwave reactor at 120 C for 20 minutes. The mixture was cooled to RT and concentrated in vacuo. The resulting residue was subjected to liquid-liquid extraction using saturated NaHCO3 (aq) and CH2Cl2. The organic layer was collected, dried over anhydrous MgSO4, filtered and removed under vacuum to afford 4.The resulting crude product 4 and 2-arylsubstitutedmalondialdehydes or 1,1,3,3tetramethoxypropane (1.0 equiv.) were dissolved in glacial AcOH (1.0 mL) and 200 proof EtOH (1.5 mL). The mixture was heated in a microwave reactor at 120 C for 20 minutes. After cooling on ice, the precipitate was collected on a fine scintered-glass frit and washed with icecold EtOH (2 x 1.0 mL). The resulting crystals 5-32 were dried and collected.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 98873-55-3, its application will become more common.

Reference:
Article; Singleton, Justin D.; Dass, Reuben; Neubert, Nathaniel R.; Smith, Rachel M.; Webber, Zak; Hansen, Marc D.H.; Peterson, Matt A.; Bioorganic and Medicinal Chemistry Letters; vol. 30; 2; (2020);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 2301-25-9, name is 1-(4-Nitrophenyl)-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 2301-25-9, name: 1-(4-Nitrophenyl)-1H-imidazole

Part B. Preparation of 1-(3-cyanophenyl)-3-methyl-5-[(4′-(N-imidazolyl)phenyl)aminocarbonyl]pyrazole The product from part A was then coupled to 1-(3-cyanophenyl)-3-methylpyrazole-5-carboxylic acid via the acid chloride methodology described previously to afford the desired amide which was then purified via standard reverse phase HPLC techniques to afford the desired material. 1 H-NMR (DMSO-d6, 300 MHz) delta: 10.73 (s,1H) 9.35 (bs,1H) 8.13 (s,1H) 7.95 (s,1H) 7.90-7.60 (complex,8H) 7.0 (s,1H) 2.30 (s,3H) ppm; ESI mass spectrum analysis m/z (rel. intensity) 369 (m+H, 100); HRMS calc. mass 369.146384; found 369.145884.

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; DuPont Pharmaceuticals Company; US6020357; (2000); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 570-22-9, 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. 570-22-9 name is 1H-Imidazole-4,5-dicarboxylic 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.

A mixture of CuCl2 (0.2 mmol, 26.9 mg), 4,5-H3imdc(0.1 mmol, 15.8 mg), and phen (0.1 mmol, 19.8 mg) in themolar ratio of 2:1:1 was dissolved in 4 mL distilled water and4 mL DMF (DMFDN,N0-dimethylformamide) and stirred30 min. Then, the mixture was transferred and sealed in10 mL glassflask heated at 85C for 96 h. After the samplewas cooled to room temperature, the crystals were washedwith distilled water and blue strip crystals werefiltered offand dried at room temperature. The yield of the blue crystalline product was 54% (based on Cu). Anal. Calcd forC17H10N4O4Cu: C, 51.28; H, 2.51; N, 14.08%. Found: C,51.13; H, 2.49; N, 14.02%. IR (KBr, cm1): 3687(w), 3045(m), 1683(m), 1572(s), 1474(s), 1428(s), 1238(m), 1107(m),995(w), 851(m), 779(w), 720(m), 675(w), 511(w).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-Imidazole-4,5-dicarboxylic acid, and friends who are interested can also refer to it.

Reference:
Article; Zhang, Huijie; Zhou, Guangpeng; Fan, Ruiqing; Wang, Xinming; Yang, Yulin; Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry; vol. 46; 8; (2016); p. 1224 – 1235;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem