Tag: M.W=0-100

Electric Literature 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.

General procedure: This compound was synthesized using a variation of the procedure previously reported [32]. Sodium hydride (60% dispersion in mineral oil, 1.56 g, 39.0 mmol) was suspended in dry THF (50 mL) under Ar at 0 C. Imidazole (2.16 g, 31.7 mmol) was dissolved in dry THF (20 mL) and added drop-wise. After 30 min, 1-bromodecane (5.41 g, 24.5 mmol) was added. The resulting reaction mixture was then stirred at room temperature overnight. After careful addition of a few drops of water to quench the remaining sodium hydride, the organic solvent was removed in vacuo, and diethyl ether (50 mL) was added. This solution was then washed with water (3 × 50 mL), dried over anhydrous MgSO4, filtered, concentrated, and then purified by flash chromatography (ethyl acetate/hexanes = 10/1 (v/v)) to give the product as a light yellow oil (yield: 4.38 g, 86%). Spectroscopic and purity data matched those reported for this compound [32].

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:
Article; Shi, Zhangxing; Newell, Brian S.; Bailey, Travis S.; Gin, Douglas L.; Polymer; vol. 55; 26; (2014); p. 6664 – 6671;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. Application In Synthesis of 1H-Imidazole

Step 1. Synthesis of 4-chloro-1H-imidazole (C33) To a solution of 1H-imidazole (22.1 g, 324 mmol) in N,N-dimethylformamide at 0 C. was added drop-wise (over 4 hours) a solution of N-chlorosuccinimide (25 g, 190 mmol) in N,N-dimethylformamide (total solvent, 160 mL). The reaction was stirred at 0 C. for 1 hour, whereupon water (200 mL) was added at 0 C. The mixture was extracted with ethyl acetate (3*50 mL), and the combined organic layers were concentrated in vacuo. Purification was carried out using supercritical fluid chromatography (Column: Princeton Cyano, 5 mum; Eluant: 15:85 methanol/carbon dioxide). The resulting material was purified again, using silica gel chromatography (Mobile phase A: ethyl acetate; Mobile phase B: [20% (2 M ammonia in methanol) in dichloromethane]; Gradient: 0% to 10% B) to afford the title compound as a white solid. Yield: 2.45 g, 23.9 mmol, 12%. GCMS m/z 102, 104 (M+). 1H NMR (400 MHz, CDCl3) delta 7.00 (d, J=1.2 Hz, 1H), 7.57 (br s, 1H), 11.3 (v br s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 288-32-4, its application will become more common.

Reference:
Patent; Pettersson, Martin Youngjin; Johnson, Douglas Scott; Subramanyam, Chakrapani; O’Donnell, Christopher John; Ende, Christopher William Am; Fish, Benjamin Adam; Green, Michael Eric; Mullins, Patrick Bradley; Stiff, Cory Michael; Tran, Tuan Phong; Navaratnam, Thayalan; US2012/252758; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 930-62-1, The chemical industry reduces the impact on the environment during synthesis 930-62-1, name is 2,4-Dimethylimidazole, I believe this compound will play a more active role in future production and life.

Compound 5.5. 5-Iodo-2,4-dimethyl-lH-imidazole. NIS (14.0g, 62.4mmol) was added portion-wise to a solution of 2,4-dimethyl- lH-imidazole (5.00 g, 52.0 mmol) in acetonitrile (100 mL). The mixture was heated at 80 C for 16 hours, then cooled to room temperature. The solvent was removed under reduced pressure and the residue was partitioned between EtOAc (300 mL) and water (80 mL). The organic layer was washed with saturated sodium thiosulfate (50 mL), brine (50 mL), dried (MgS04) and concentrated under reduced pressure. The residue was purified with by silica gel column chromatography (hexanes:EtOAc 1 : 1 to 10% MeOH in EtOAc) to yield the title compound as a light yellow solid (8.56 g, 74%). m/z (ES+) 223(M+H)+. NMR (400 MHz, CDC13) delta 9.69 (br s, 1H), 2.38 (s, 3H), 2.19 (s, 3H)

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, 2,4-Dimethylimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; 3-V BIOSCIENCES, INC.; HEUER, Timothy Sean; OSLOB, Johan D.; MCDOWELL, Robert S.; JOHNSON, Russell; YANG, Hanbiao; EVANCHIK, Marc; ZAHARIA, Cristiana A.; CAI, Haiying; HU, Lily W.; WO2015/95767; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 616-47-7,Some common heterocyclic compound, 616-47-7, name is 1-Methyl-1H-imidazole, molecular formula is C4H6N2, 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.

Triethylamine (3.40 mL, 24.4 mmol) and Ethyl chloroformate (2.34 mL, 24.4 mmol) were added at 0 C. to an acetonitrile (4.0 mL) solution of 1-methyl-1H-imidazole (1.00 g, 12.2 mmol), and the reaction solution was stirred at room temperature for 16 hours. The reaction solution was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, hexane/ethyl acetate), thereby obtaining ethyl 1-methyl-1H-imidazole-2-carboxylate (1.50 g, 9.73 mmol, 80%) as a white solid.1H-NMR (400 MHz, CDCl3) delta: 1.42 (3H, t, J=7.2 Hz), 4.01 (3H, s), 4.40 (2H, q, J=7.2 Hz), 7.01-7.03 (1H, m), 7.13-7.15 (1H, m)ESI-MS: m/z=155 (M+H)+

The synthetic route of 616-47-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Toray Industries, Inc.; Takahashi, Hirozumi; Baba, Yoko; Morita, Yasuhiro; Iseki, Katsuhiko; Izumimoto, Naoki; (19 pag.)US2020/172507; (2020); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. Recommanded Product: 1H-Imidazole

General procedure: A mixture of aryl halide (1.0 mmol), Het-NH (1.2mmol) or amine (4 mmol), KOH (2 mmol), Cu2O/nano-CuFe2O4 magnetic composite (0.010 g) and anhydrous DMSO (2 mL) was stirred at 100 C. After completion of the reaction as indicated by TLC, the reaction mixture was cooled to room temperature and with diluted ethyl acetate and the catalyst was separated by an external magnet from the mixture, washed with acetone, dried in an oven at 80 C for 3 h and re-used for a consecutive run under the same reaction conditions. The combined ethyl acetate layer was washed with water, dried over anhydrous MgSO4, The residue was purified by recrystallization or short column chromatography on silica gel to afford the target products in excellent yield.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 288-32-4, its application will become more common.

Reference:
Article; Elhampour, Ali; Nemati, Firouzeh; Kaveh, Mahdieh; Chemistry Letters; vol. 45; 2; (2016); p. 223 – 225;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 57090-88-7, These common heterocyclic compound, 57090-88-7, name is 1H-Imidazole-4-carbonitrile, 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 soluiton of 1H-imidazole-4-carbonitrile (300 mg, 3.2 mmol) in THF (50 mL) was added LiA1H4 (365 mg, 9.6 mmol). After stirred at reflux overnight, the reaction mixture was quenched by H20 (2 mL). And the mixture was dried over anhydrous Na2SO4 and filtered. The filtrate was evaporated in vacuum. The residue was used for next step without further purification.

Statistics shows that 1H-Imidazole-4-carbonitrile is playing an increasingly important role. we look forward to future research findings about 57090-88-7.

Reference:
Patent; SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE; GARDELL, Stephen; PINKERTON, Anthony B.; SERGIENKO, Eduard; SESSIONS, Hampton; (428 pag.)WO2018/132372; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 7098-07-9, A common heterocyclic compound, 7098-07-9, name is 1-Ethyl-1H-imidazole, molecular formula is C5H8N2, 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.

In a 100 mL three-necked flask, TMEDA (2.86 g, 3.72 ml, 24.7 mmol, Eq: 2.37) was combined with pentane (10 ml) to give a colorless solution. N-BuLi 1.6M in hexane (15.6 ml, 25.0 mmol, Eq: 2.4), followed by 1-ethyl-1H-imidazole (1 g, 10.4 mmol, Eq: 1.00) were added dropwise at -25° C. for 30 min. The reaction mixture was stirred at RT for 1 h (light yellow suspension). Afterwards, the suspension was cooled to -65° C. and THF anhydrous (30 ml) was added (-65° C. to -48° C.). A solution of iodine (3.83 g, 15.1 mmol, Eq: 1.45) in THF anhydrous (20 ml) was added dropwise to the reaction mixture (internal temperature remained below -55° C.)=>brown suspension. Stirring was continued as the reaction was gradually warmed to 0° C. during 1.3 hours (brown milky solution). Eventually, the reaction was quenched by adding 4 mL of methanol. Work up: The reaction mixture was poured into 50 mL sat. Na2SO3 and extracted with EtOAc (2*100 mL). The organic layers were combined, washed with brine, dried over Na2SO4, and concentrated i. V. Purification: The crude material was purified by flash chromatography (silica gel, 50 g, 20percent to 100percent EtOAc in heptane) to provide in the more polar fractions 417 mg of the desired title compound as yellow oil. MS (ESI): 222.9 [M+H]+.

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; HOFFMANN-LA ROCHE INC.; Aebi, Johannes; Amrein, Kurt; Hornsperger, Benoit; Kuhn, Bernd; Maerki, Hans P.; Mayweg, Alexander V.; Mohr, Peter; Tan, Xuefei; US2014/128429; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 7098-07-9, name is 1-Ethyl-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 7098-07-9, category: imidazoles-derivatives

A mixture of CoCl26H2O (0.1705 g, 0.8 mmol), NH4VO3(0.1404 g, 0.8 mmol), eIM (0.8 mL), and H2O (8 mL) was heated at about 120 °C for 72 h. After the mixture was cooled to room temperature, dark purple crystals were isolated from the mixture. Yield: 62percent (based on NH4VO3); Anal. Calcd. for C30H52Co2N12O14V4(percent): C, 31.96; H, 4.61; N, 14.91. Found: C, 31.71; H, 4.42; N, 14.58.

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

Reference:
Article; Niu, Yan-Hong; Yang, Song; Li, Ji-Kun; Xu, Yan-Qing; Hu, Chang-Wen; Chinese Chemical Letters; vol. 27; 5; (2016); p. 649 – 654;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature 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.

(1) Preparation of nitric-sulfuric mixed acid: at 10 C, sequentially, in a beaker 54mL of fuming sulfuric acid and slowly dropping 12.8mL of fuming nitric acid and during adding process of fuming nitric acid attention to keep stirring; (2) At room temperature, 22 mL of fuming sulfuric acid and 13.6 g (0.2 mol) of imidazole were added slowly to a three-necked flask, the reaction continuously stirred for 30 min, and the mixture was thoroughly mixed. The temperatures was then set to 65 C and after reaching to a corresponding temperature add the whole nitric-sulfuric mixed acid prepared above, and reaction was carried out for 1h. After the end of the reaction, slowly poured into 550g ice water, stirring it until it is melt, and then heated to 120 C and reacted for 1h. then cooling, suction and drying was carried out to obtain 4-NI;

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:
Patent; North University of China; Liu Yucun; Luo Jin; Liu Yan; Chai Tao; (14 pag.)CN106831598; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 288-32-4, 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. 288-32-4, name is 1H-Imidazole, This compound has unique chemical properties. The synthetic route is as follows.

Under ice-cooling, sodium hydride (60%, 1.40 g, 35 mmol) was added in one portion to dry tetrahydrofuran (25 mL), and the resulting reaction solution was warmed to room temperature and stirred for 30 minutes.Under ice-cooling, 1H-imidazole (2.00 g, 30 mmol, 6 mL of dry THF solution) was added dropwise, and the resulting reaction solution was warmed to room temperature and stirred for 1.5 h.1-Bromo-3-chloropropane (4.60 g, 30 mmol) was added dropwise and the reaction was allowed to react at room temperature overnight.Methanol (5 mL) was added to the reaction system in one portion, filtered, the solvent was distilled off under reduced pressure, and the crude product was purified by column chromatography (dichloromethane/methanol (V/V) = 30/1).A pale yellow oil (3.10 g, 73%) was obtained.

The chemical industry reduces the impact on the environment during synthesis 1H-Imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, YINGJUN; ZHANG, JIANCUN; WANG, XIAOJUN; LIN, RUNFENG; CAO, SHENGTIAN; WANG, ZHAOHE; LI, JING; (226 pag.)TWI607995; (2017); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem