Author: Jessica.F

Application of 4856-97-7,Some common heterocyclic compound, 4856-97-7, name is (1H-Benzoimidazol-2-yl)methanol, molecular formula is C8H8N2O, 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.

The procedure for gram scale oxidation of (1H-benzo[d]imidazol-2-yl)methanol to 1H-benzo[d]imidazole-2-carbaldehydewas as follows: (1H-benzo[d]imidazol-2-yl)methanol (0.1 mol,14.8 g) and [Ru(bpbp)(pydic)] (0.001 mmol, 7.32 ¡Á 10-3 g) wereadded into a reactor. The reactor containing this mixture was heatedto 50 C in an oil bath under vigorous stirring and then 30% H2O2(30 mL, 0.3 mol) was slowly dropwise over a period of 30 min. The mixture was stirred for 5 h. After filtering, the solution wasevaporation under reduced pressure at 50 C. Pure 1H-benzo[d]imidazole-2-carbaldehyde (0.07 mmol, 10.2 g) was obtained with ayield of 70% after recrystallisation from 30% H2SO4 solution. Theproduct, 1H-benzo[d]imidazole-2-carbaldehyde, was identified byits 1H NMR spectrum.

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

Reference:
Article; Liu, Shenggui; Pan, Rongkai; Su, Wenyi; Li, Guobi; Ni, Chunlin; Journal of Chemical Research; vol. 41; 2; (2017); p. 88 – 92;,
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. 2301-25-9, name is 1-(4-Nitrophenyl)-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 1-(4-Nitrophenyl)-1H-imidazole

Part A. Preparation of 1-(4-aminophenyl)imidazole. 1-(4-Nitrophenyl)imidazole (5.0 g) and 200 mL of methanol were combined to form a solution at ambient temperature. The addition of a catalytic amount of 10% palladium on carbon turned the solution into a suspension. Placement of the reaction mixture under a hydrogen atmosphere initiated the reduction. The reaction proceeded overnight (15 h) at ambient temperature. Filtration through a celite pad separated out the catalyst. Concentration of the filtrate under reduced pressure gave the title product as a pale yellow solid (3.99 g). 1 H-NMR(DMSO d6) delta: 7.95 (s, 1H), 7.45 (s, 1H), 7.18 (d, 2H), 6.99 (s, 1H), 6.60 (d, 2H), 5.25 (s, 2H) ppm. LRMS(GC/MS) m/z 160 (M+H, 100).

The synthetic route of 2301-25-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DuPont Pharmaceuticals Company; US6020357; (2000); 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. 71759-89-2, name is 5-Iodo-1H-imidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 71759-89-2

Intermediate 4.1 : (5-chloro-2-nitro-phenyl)-(lH-imidazol-4-yl) methanol To a solution of 4-iodo-lH-imidazole (2 g, 10.3 mmol) in THF (20 mL) was added dropwise isopropylmagnesiumchloride (2 M in THF, 12 mL, 23.7 mmol) at room temperature. The reaction solution was stirred at rt for 2 h. To this solution was added 5-chloro-2-nitro-benzaldehyde (2.9 g, 15.5 mmol) in 10 mL THF. The solution was stirred at room temperature for 2 h. The reaction was quenched with aqueous NH4CI solution. The mixture was extracted twice with EA. The combined organic phases were dried and concentrated in vacuo. The residue was purified silica gel chromatography column (PE/EA, 3/1 to 1/1) to give the title compound as a brown solid

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; LEO PHARMA A/S; SOERENSEN, Morten Dahl; LARSEN, Jens Christian Hoejland; NOERREMARK, Bjarne; LIANG, Xifu; HUANG, Guoxiang; WO2013/82751; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 103057-10-9, name is 4-(Chloromethyl)-1-trityl-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 103057-10-9, COA of Formula: C23H19ClN2

Example 8 Preparation of bis(2,2,2-trifluoroethyl)(1-triphenylmethylimidazol-4-yl)methylphosphonate: To a solution of bis(2,2,2-trifluoroethyl)phosphite (0.11 ml, 0.6 mmol) in THF (1.5 ml) were added 1,8-diazabicyclo[5,4,0]-7-undecene (DBU) (0.09 ml, 0.6 mmol) and (1-triphenylmethylimidazol-4-yl)methyl chloride (71.8 mg, 0.2 mmol). The reaction mixture was refluxed under argon flow for 22 hours. The solvent was removed under reduced pressure, and water (10 ml) was added to the residue, which was then extracted 3 times with ethyl acetate (10 ml). The resultant organic layers were washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The obtained white solid was purified through chromatography on silica gel column using ethyl acetate – hexane (3:2) to give bis(2,2,2-trifluoroethyl)(1-triphenylmethylimidazol-4-yl)methylphosphonate (34 mg, 30%) as a white powder. This powder was recrystallized from a mixture of ethyl acetate and hexane to provide a white small needle crystal (m.p. 145-148C). 1H NMR (CDCl3) d 3.34 (d, J = 10.5 Hz, 2H), 4.30 (quint, d, J = 3.9 Hz, 1.3 Hz, 4H), 6.80 (s, 1H), 7.08-7.50 (m, 16H). 31P NMR(CDCl3) d 29.9 (s). Anal Calcd for C27H23N2O3PF6: C, 57.03; H, 4.08; N, 4.93. Found: C, 57.03; H, 4.19; N, 4.94.

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; Azwell Inc.; EP1477487; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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 3314-30-5 as follows. name: 1H-Benzo[d]imidazole-2-carbaldehyde

General procedure: The appropriate imidazolecarboxaldehyde derivative (10 mmol, 1 equiv.) was dissolved inmethanol. The amine (1 equiv.) in dry THF (5.0 mL), and activated 4 molecular sieves (2.00 g) wereadded. The reaction mixture was stirred at room temperature, under nitrogen for 12 hours. Then,sodium borohydride (1.2 equiv.) was added portionwise and the reaction was stirred at roomtemperature. After 3 hours water was added, and the mixture was stirred for 10 minutes. Molecular sieves were filtered off through a Celite pad. The filtrate was evaporated under reduced pressure.The residue was taken up with EtOAc and the organic layer was washed with 2N NaOH ( ¡Á 1), driedover sodium sulfate and concentrated in vacuo. The crude material was purified by columnchromatography using the indicated eluents

According to the analysis of related databases, 3314-30-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Galli, Ubaldina; Hysenlika, Rejdia; Meneghetti, Fiorella; Grosso, Erika Del; Pelliccia, Sveva; Novellino, Ettore; Giustiniano, Mariateresa; Tron, Gian Cesare; Molecules; vol. 24; 10; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 10394-38-4, A common heterocyclic compound, 10394-38-4, name is 1-Methylbenzoimidazol-5-amine, molecular formula is C8H9N3, 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.

To a suspension of 6-(4-((2,5-dichloropyrimidin-4-yl)amino)piperidin-l- yl)pyridazine-3-carbonitrile (285.8 mg, 0.82 mmol) and l-methyl-li7-benzo[Patent; SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES, LLC; XI, Ning; LI, Minxiong; PENG, Ju; LI, Xiaobo; ZHANG, Tao; HU, Haiyang; CHEN, Wuhong; BAI, Changlin; KE, Donghua; CHEN, Peng; (281 pag.)WO2019/99311; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 288-32-4, 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 288-32-4 as follows.

To a solution of 1H-Imidazole (5 g, 73.5 mmol) in THF was added sodium hydride (1.8 g, 45 mmol) and stirred at room temperature for 0.5 hour before addition of then bromo-acetonitrile (8.8 g, 73.9 mmol) and stirring at room temperature for 2 hours. The reaction was quenched via the addition of water (50 mL) and saturated ammonium chloride (50 mL) solution and the mixture was extracted with ethyl acetate (100 mL*3). The combined organics layer was dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude residue was purified on silica gel (petroleum ether:ethyl acetate=10:1) to afford 2-(1H-imidazol-1-yl)acetonitrile (4.6 g, 59%) as a yellow oil. LRMS m/z: 108 [M+H+].

According to the analysis of related databases, 288-32-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Albrecht, Brian K.; Bellon, Steven F.; Gehling, Victor S.; Harmange, Jean-Christophe; LeBlanc, Yves; Liang, Jun; Magnuson, Steven; Tsui, Vicki; Zhang, Birong; US2015/65522; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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 288-32-4 as follows. HPLC of Formula: C3H4N2

To a solution of imidazole (13.6 g, 0.2 mol) in 1 L of DCM was added BrCN (7.4 g, 66 mmol), and the mixture was heated at reflux for 30 minutes. The mixture was cooled to RT, and the white precipitate removed by filtration, and the filtrate concentrated to 100 mL then cooled to 0 C. for 2 days. The crystallized solid was filtered and washed with cold DCM, then dried in vacuo to give the desired product (8.8 g) as a white solid.

According to the analysis of related databases, 288-32-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Merck Sharp & Dohme Corp.; Coburn, Craig A.; Ludmerer, Steven W.; Liu, Kun; Wu, Hao; Soll, Richard; Zhong, Bin; Zhu, Jian; (155 pag.)US2019/127365; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 106429-59-8, 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. 106429-59-8, name is 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows.

Step 4.5-((7-(5-((5-fluoro-2′-isopropyl-[1,1′-biphenyl]-2-yl)oxy)pyrimidin-4-yl)-2,7- diazaspiro[4.4] nonan-2-yl)methyl)-1H-benzo[d]imidazol-2(3H)-one (0987) A mixture of 2-(5-((5-fluoro-2′-isopropyl-[1,1′-biphenyl]-2-yl)oxy)pyrimidin-4- yl)-2,7-diazaspiro [4.4]nonane (6.8 g, 15.7 mmol), 2-oxo-2,3-dihydro-1H- benzo[d]imidazole-5-carbaldehyde (Intermediate 40, 3.05 g, 18.8 mmol), NaBH3CN (3.9 g, 62.8 mmol) and HOAc (3.4 mL) in MeOH (130 mL) was stirred at 70 C for 18 h. The mixture was then concentrated under reduced pressure and the residue adjusted to pH = 8 with saturated NaHCO3 solution and extracted with ethyl acetate (3 ¡Á 150 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by basic preparative RP- HPLC method D to give 5-((7-(5-((5-fluoro-2′-isopropyl-[1,1′-biphenyl]-2- yl)oxy)pyrimidin-4-yl)-2,7-diazaspiro[4.4]nonan-2-yl)methyl)-1H-benzo[d]imidazol- 2(3H)-one as a slight yellow solid. Yield: 7.2 g. LCMS method C: Rt = 0.663 min; (M+H)+ = 579.1.1H NMR (CD3OD): delta 8.13 (s, 1H), 7.58 (d, J = 6.8 Hz, 1H), 6.95-7.35 (m, 10H), 3.62 (s, 2H), 3.40-3.55 (m, 3H), 2.55-2.85 (m, 4H), 2.30-2.45 (m, 2H), 1.65- 1.85 (m, 4H), 1.00-1.10 (m, 6H).

The chemical industry reduces the impact on the environment during synthesis 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carbaldehyde. I believe this compound will play a more active role in future production and life.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; CACATIAN, Salvacion; CLAREMON, David, A.; DILLARD, Lawrence, Wayne; DONG, Chengguo; FAN, Yi; JIA, Lanqi; LOTESTA, Stephen, D.; MARCUS, Andrew; MORALES-RAMOS, Angel; SINGH, Suresh, B.; VENKATRAMAN, Shankar; YUAN, Jing; ZHENG, Yajun; ZHUANG, Linghang; PARENT, Stephan, D.; HOUSTON, Travis, L.; (444 pag.)WO2017/214367; (2017); 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. 3012-80-4, name is 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C9H8N2O

General procedure: Benzimidazole 1 or 2 (1 mmol)was added to the mixture of TfOH (1 mL) or H2SO4 (2 mL) and arene (2-18 mmol). Reactionmixture was stirred at room temperature for the time as indicated in Table 3 or Scheme 2. Themixture was poured into ice water (30 mL). After extraction with CH2Cl2 (3 ¡Á 30 mL), thecombined extracts were consequently washed with water (50 mL), saturated aqueous solution ofNa2CO3 (30 mL), water (50 mL), dried with anhydrous Na2SO4 and evaporated in vacuo to givecrude products, which was subjected to chromatographic separation on silica gel using petroleumether/diethyl ether as an eluent.

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 3012-80-4.

Reference:
Article; Ryabukhin, Dmitry S.; Turdakov, Alexey N.; Soldatova, Natalia S.; Kompanets, Mikhail O.; Ivanov, Alexander Yu.; Boyarskaya, Irina A.; Vasilyev, Aleksander V.; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1962 – 1973;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem