Month: February 2021

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. 50995-95-4, name is 2-Propylimidazole, A new synthetic method of this compound is introduced below., COA of Formula: C6H10N2

Copper (I) Iodide (0.038g) and D-histidine (0.062g) in DMSO (15ml) was stirred under an atmosphere of argon at 11O0C for 30 minutes when 3-(4-bromophenyl)-1 ,4- diazaspiro[4.5]dec-3-en-2-one (D6) (0.614g), 2-propylimidazole (264mg) and potassium carbonate (0.553g) was added and heating was continued at 11 O0C for 5 days when the mixture was poured into a mixture of sodium bicarbonate solution and ethyl acetate. The mixture was stirred for 2 hours, filtered and the filtrate was separated. The ethyl acetate layer was dried over sodium sulphate, evaporated and the residue was chromatographed on a silica column eluted with 0-5% 2M methanolic ammonia/DCM to give the title compound (0.2g).1H NMR (CDCI3) delta: 1.4 (3H, t), 1.5 – 1.85 (obs, m), 1.9 – 2.1 (4H, m) 2.7 (2H, t), 7.00 (1 H, m), 7.09 (1 H, m), 7.4 (2H, m), 7.82 (1 H, br), 8.55 (2H, m). Mass Spectrum (LC/MS): Found 337 (MH+). Ret. time 1.87 min.

The synthetic route of 50995-95-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/34061; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 106429-57-6, name is Methyl 2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-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 106429-57-6, COA of Formula: C9H8N2O3

A suspension of benzimidazolone 2 (25.0 g, 0.130 mol, 1 eq) in POCl3 (150 mL) was heated to reflux for 7 h. The excess of POCl3 was evaporated and the residue was neutralized with saturated NaHCO3 solution. The precipitate was collected by filtration and dried in vacuo. The aqueous phase was extracted with DCM, dried over MgSO4 and the solvent was removed under reduced pressure. The light brown solids obtained this way were of high purity and could be used in the next step without further purification (19.7 g, 93.6 mmol, 72 %).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Article; Zellmann, Felix; Thomas, Laura; Scheffer, Ute; Hartmann, Roland K.; Goebel, Michael W.; Molecules; vol. 24; 4; (2019);,
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. 3543-72-4, name is Ethyl 4-(1-methyl-5-nitro-1H-benzo[d]imidazol-2-yl)butanoate, A new synthetic method of this compound is introduced below., Safety of Ethyl 4-(1-methyl-5-nitro-1H-benzo[d]imidazol-2-yl)butanoate

Example 3 Synthesis of ethyl 4-(5-amino-1-methyl-1H-benzimidazol-2-ylbutanoate (6) 163 g (559.5 mmol) of compound (5) were dissolved in 1875 g ethanol. 14 g of palladium catalyst on activated carbon doped with iron (5% Pd, 1% Fe) and an additional 0.8 g of iron (II) sulfate 7-hydrate or 0.8 g of iron (III) nitrate 9-hydrate were added. Compound (5) was 10 then hydrogenated at a hydrogen pressure of up to 4 bar until complete conversion of the starting compound (5). The catalyst was removed by filtration, and the ethanolic solution concentrated until a dry product remained. This residue was crystallized from propan-2-ol or ethyl acetate. The yield of compound (6) was 128 g (489.8 mmol) with a content of >99% (87.5% of theory). The overall yield of compound ( 6) was 80.4% of theory in relation to 2-fluoro-5-nitroaniline. In comparison, the synthesis according to DD34727 starting from N-1-methyl-4-nitrobenzene-1,2-diamine (CAS 41939-61-1) is characterized by a yield of 39.0%.

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; Heyl Chemisch-pharmazeutische Fabrik GmbH & Co. KG; Frey, Michael; Walther, Dirk-Detlef; US2014/31560; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 16681-59-7, 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. 16681-59-7, name is 2-Bromo-1-methyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

a) Synthesis of 1-(1-methyl-1H-imidazol-2-yl)piperazine 1.0 g (6.2 mmol) 2-bromine-1-methyl-1H-imidazol was fused with 3.2 ml (37.0 mmol) piperazine at 145 C. and stirred for 18 h at this temperature. After cooling to RT, the residue was received in 10% aq. hydrochloric acid and washed with AE. Alkalic adjustment was subsequently performed with a 10% aq. NaOH sol. (pH>12) and extraction with DCM. The organic phase was dried over MgSO4, filtered and concentrated in a vacuum. In this process, 780 mg (4.7 mmol, 76%) 1-(1-methyl-1H-imidazol-2-yl)piperazine was obtained.

The synthetic route of 2-Bromo-1-methyl-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Grunenthal GmbH; US2008/261996; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 150058-27-8, A common heterocyclic compound, 150058-27-8, name is Methyl 2-ethoxy-1H-benzo[d]imidazole-7-carboxylate, molecular formula is C11H12N2O3, 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 500 mL flask was added 200 mL of acetone,Ethoxybenzimidazole-7-carboxylate (XIII, 22.0 g,0.10 mol),K2CO3 (17.9 g, 0.13 mol) and 4-bromomethyl-2′-cyanobiphenyl (28.6 g, 0.105 mol).The temperature was raised to reflux and reaction was complete until TLC disappeared (about 5 to 8 hours).

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; Zhejiang Huahai Pharmaceutical Co., Ltd.; Zhejiang Huahai Zhicheng Pharmaceutical Co., Ltd.; Jin Congyang; Wang Jiquan; Zhang Wenling; Wang Peng; (8 pag.)CN107089972; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 670-96-2,Some common heterocyclic compound, 670-96-2, name is 2-Phenyl-1H-imidazole, molecular formula is C9H8N2, 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.

Placing 2-phenylimidazole in an amount of 8.6 g (60 mmol) into a flask having a dropping funnel, and after replacing the atmosphere with argon gas, 180 milliliter of tetrahydrofuran was added. Under cooling with ice, n-butyllithium of 1.56 mol/liter in an amount of 39.1 milliliter (61 mmol) was dripped down into the solution spending 30 minutes and subsequently, 8.6 g(61 mmol) of methyl iodide dissolved into 10 milliliter of tetrahydrofuran was dripped down. After termination of dripping down, the resultant solution was reacted at the room temperature for 3 hours. Concentrating the reacted solution and extracting the resultant solid using 150 milliliter of methylene chloride, it was washed three times using 150 milliliter of water. After drying an organic layer with the use of magnesium sulfate, the solvent was removed. Refining the crystals by means of silicagel column (hexane / methylene chloride), 6.1 g of 1-methyl-2-phenylimidazo Intermediate6-1b as white crystals was obtained (yield: 69 %). The white crystals were confirmed as the aimed compound from 1H-NMR spectrum. The measurement result is shown as follows: 1H-NMR(CDCl3): delta 7.29-7.67 (m,5H), delta 6.93-7.10 (m,2H), delta 3.69 (s,3H)

The synthetic route of 670-96-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IDEMITSU KOSAN CO., LTD.; EP1647554; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 15108-18-6, 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. 15108-18-6, name is 2-Hydrazinyl-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 2-hydrazinobenzimidazole (750 mg;5mmol) in a mixture of 10mL of water and 0.75mL of concentrated HCl was gradually added 1,1,3,3-tetramethoxypropane(820mL; 5mmol). The resulting mixture was heated at reflux for 2 h, then was allowed to cool and filtered.The filtrate was neutralised with solid potassium carbonate,causing the product to precipitate as a pale tan solid, which was filtered and dried in vacuo. Yield 650mg (71%). m.p. 233-2358C; dH(500MHz, d6-DMSO) 6.66 (m, br, 1H,H2), 7.19-7.21 (m, 2H, H6 H7), 7.46 (d, 1H, J 6.1 Hz,H5), 7.58 (d, 1H, J 7.7 Hz, H8), 7.94 (d, 1H, J 1.5 Hz,H3), 8.59 (d, 1H, J 2.9 Hz, H1), 13.10 (s, br, 1H, H4);dC(125MHz, d6-DMSO) 109.2, 111.6, 118.4, 122.2, 122.5,129.1, 133.7, 141.7, 142.9, 146.1; m/z (HR-ES-MS)185.0821 ([M H], calculated for C10H9N4 185.0822);y max(KBr)/cm21 2943m br, 1628m, 1574s, 1479m, 1460s,1387m, 1324m, 1273m, 1226m, 1076s, 927s, 740s.

The synthetic route of 2-Hydrazinyl-1H-benzo[d]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hawes, Chris S.; Kruger, Paul E.; Supramolecular Chemistry; vol. 27; 11-12; (2015); p. 757 – 771;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 137049-00-4, name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, 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. Recommanded Product: 137049-00-4

To a precooled (0 C) solution of intermediate 2.93 (20. mg, 0.066 mmol) in dichloromethane (0.5 mL) was added triethylamine (30 muL, 0.2 mmol) and 1-methyl-1H- imidazole-4-sulfonyl chloride (18 mg, 0.098 mmol). The resulting mixture was allowed to warm to room temperature and stirred for 15 h, then diluted with wet DMSO (0.5 mL), filtered through Celite and purified via mass-directed isolation using ultra-performance liquid chromatography (15 mg, 52% yield).1H NMR (500 MHz, Acetonitrile-d3) d 8.85 (s, 1H), 7.77- 7.65 (m, 2H), 7.53 (dd, J = 12.3, 1.5 Hz, 2H), 7.39 (t, J = 8.5 Hz, 1H), 7.32- 7.24 (m, 1H), 7.21- 7.10 (m, 2H), 7.10- 7.02 (m, 1H), 4.36 (dd, J = 13.3, 4.3 Hz, 1H), 3.68- 3.58 (m, 4H), 3.06- 2.94 (m, 1H), 2.94- 2.86 (m, 2H); AMM 449.0869 (ESI) m/z [calc for C20H19ClFN4O3S (M+H)+ 449.0850]. (0467)

The synthetic route of 1-Methyl-1H-imidazole-4-sulfonyl chloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE TRUSTEES OF THE UNIVERSITY OF PENNSYLVANIA; VAL-CHUM, LIMITED PARTNERSHIP; GRENIER, Melissa Carey; SMITH, Amos B., III; FINZI, Andres; DING, Shilei; CHAPLEAU, Jean-Philippe; (240 pag.)WO2020/28482; (2020); 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. 1402838-08-7, name is 2-(1-Trityl-4-imidazolyl)benzaldehyde, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2-(1-Trityl-4-imidazolyl)benzaldehyde

In the atmosphere of nitrogen,Dimethyl methylphosphonate (402 mg, 3.24 mmol, 1.5 equiv)Dissolved in 5 ml of dry tetrahydrofuran.Cool to -60C with dry ice/ethanol.n-Butyllithium (1.70 ml, 2.5 mol/ml n-hexane solution, 4.32 mmol, 2 eq.) was slowly added dropwise.The mixture is stirred at this temperature for 30 minutes.The compound 6-fluoro-2-methylbenzofuran-5-carboxylic acid methyl ester (0303-69) (450 mg, 2.16 mmol, 1 eq.) was slowly added dropwise.A solution of tetrahydrofuran (5 ml).The mixture was stirred at this condition for 1 hour. Isopropanol (15 ml), cesium carbonate (1.0 g, 3.24 mmol, 1.5 eq) and 2-(1-Tri) were addedBenzyl-1H-imidazol-4-yl)benzaldehyde (0105-1) (894 mg, 2.16 mmol, 1 eq.) stirred at room temperatureAfter 16 hours, after the reaction was completed, water (50 ml) was added and the mixture was extracted with ethyl acetate. The organic phase was washed with saturated brine and anhydrous sulfuric acid.The sodium was dried, concentrated under reduced pressure, and purified by silica gel column chromatography to give the product 1-(6-fluoro-2-methylbenzofuran-5-yl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one (530 mg, yield 41.9%).

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 1402838-08-7.

Reference:
Patent; Guangzhou Bi Beite Pharmaceutical Co., Ltd.; Cai Xiong; Qian Changgeng; Weng Yunwo; Qing Yuanhui; Liu Bin; Lin Mingsheng; Wang Yanyan; (126 pag.)CN107383024; (2017); A;,
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. 79917-88-7, name is 1,3-Dimethyl-1H-imidazol-3-ium chloride, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 1,3-Dimethyl-1H-imidazol-3-ium chloride

1) 33.81 g of 1,3-dimethylimidazolium chloride (purity 99percent) and 7.6 g of NH4F (purity 98percent) were respectively taken, and the two solids were directly placed in an Erlenmeyer flask and ultrasonically shaken in a water bath at 50 ¡ãC. 8h, the solid will undergo a metathesis reaction to produce a white precipitate, which is allowed to stand, precipitate and settle, and the upper layer is a liquid phase with suspended particles to obtain a layered mixture after standing;2) pumping the layered phase at a low pressure three times to obtain a filtrate and a filter residue;3) The liquid phase obtained by filtration is vacuum-screwed at 60 ¡ã C to obtain a pale yellow clear liquid;4) Dry the light yellow clear solution at 70 ¡ã C for 24 h to obtain a light yellow viscous liquid, which is a 1,3-dimethylfluoroimidazole product, label L4, using a small glass bottle and taking two drops of product for Raman Spectral detection test to check whether the product contains NH4+, compare the spectral results of the sample with the standard Raman spectrum of NH4+, if the comparison shows the presence of NH4+The Raman vibration band continues to dry at 100 ¡ã C under high vacuum until the Raman vibration band without NH4+ is detected. If the Raman vibration band without NH4+ is detected, the obtained 1,3-dimethylfluorinated imidazolium ionic liquid is weighed. 23.19g.

According to the analysis of related databases, 79917-88-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Northeastern University (disambiguation); Hu Xianwei; Niu Chunbo; Shi Zhongning; Gao Bingliang; Yu Jiangyu; Wang Zhaowen; (11 pag.)CN108586347; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem