Category: imidazoles-derivatives

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. 150058-27-8, name is Methyl 2-ethoxy-1H-benzo[d]imidazole-7-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Formula: C11H12N2O3

The 44g intermediate 2-ethoxy -1H-benzimidazole-7-carboxylic acid methyl ester and 300 ml of methanol are added to a reaction flask, opening stirring, add 120g10percent sodium hydroxide solution, to return thermal insulation reaction, with used in HPLC. After the reaction is complete, cooling to 15-25°C, dropwise 10percent dilute hydrochloric acid, to pH adjusting 1-2, stirring the accent finishes 1h, filtering, used 30 ml purified water washing, filtering to dry, for 55-65 °C reduced-pressure drying to the stem, be 2-ethoxy -3H-benzimidazole-7-carboxylic acid 37.9g, yield 92.0percent, purity 98.3percent

The synthetic route of 150058-27-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Long days Chongqing Pharmaceutical Co., Ltd; Meng, Wenxue; Long, Daobing; Chen, Shunxiang; (14 pag.)CN105622595; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 71759-89-2, These common heterocyclic compound, 71759-89-2, name is 5-Iodo-1H-imidazole, 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 solution of 4-iomethyl-1H-imidazole (970 mg, 545 mmoles) in DMF (10 mL) is added NaH 60% dispersion inmineral oil (220 mg, 5.5 mmoles). The reaction mixture isheated at 50 C. for 1 h, then 2-bromoethylbenzene (781 f.LL,5.5 mmoles) and a catalytic quantity oftetrabutylammoniumbromide are added to the mixture. The reaction mixture is50 then heated at 80 C. for 5 hours. Half-saturated ammoniumchloride solution is added, and the aqueous phase is extractedthree times with Et20. The organic phase is washed withwater, brine, dried over magnesium sulphate, filtered and the solvent is removed under reduced pressure. The residue is purified by silica gel chromatography using (heptane:AcOEt)as eluentwithagradientfrom (95:5)to (60:40)to give4-iodo-1-phenethyl-imidazole and 5-iodo-1-phenethyl-imidazole.4-iodo-1-phenethy 1-imidazole1H NMR: 7.38-7.15 (m, 4H), 7.10-6.96 (m, 2H), 6.93 (s,lH), 4.14 (t, J=8.5 Hz, 2H), 3.04 (t, J=8.5 Hz, 2H).5-iodo-1-phenethyl-imidazole1H NMR: 7.41 (s, lH), 7.36-7.18 (m, 3H), 7.15-7.00 (m,3H), 4.15 (t, J=8.6 Hz, 2H), 3.04 (t, J=8.6 Hz, 2H).

Statistics shows that 5-Iodo-1H-imidazole is playing an increasingly important role. we look forward to future research findings about 71759-89-2.

Reference:
Patent; BIOPROJET; Berrebi-Bertrand, Isabelle; Billot, Xavier; Calmels, Thierry; Capet, Marc; Krief, Stephane; Labeeuw, Olivier; Lecomte, Jeanne-Marie; Levoin, Nicolas; Ligneau, Xavier; Robert, Philippe; Schwartz, Jean-Charles; (73 pag.)US9255101; (2016); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 2620-76-0, name is 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, 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 2620-76-0, HPLC of Formula: C19H13BrN2

[0104] Compound 26: A mixture of Compound 25 (4- (diphenylamino)phenyl)boronic acid (900 mg, 3.1 mmol), Compound 9 (1.09 g, 3.1 mmol), Pd(PPh3)4 (180 mg, 0.16 mmol) and K2CO3 (1.38 g, 10 mmol) in 1,4- dioxane/H2O (25 mL/5 mL) was degassed and the resulting mixture was heated at about 100 0C overnight under an argon atmosphere. After cooling to room temperature, the resulting mixture was poured into water, extracted with ethyl acetate (100 mL x 2). The organic phase was dried over Na2SO4 and filtered. After addition of hexanes (100 mL), a yellow precipitate formed after about one hour. Filtration gave a yellow solid (760 mg) and the filtrate was absorbed on silica gel and purified by flash chromatography to give a yellow solid (200 mg). The total amount of product (Compound 26) was 960 mg in 62% yield.

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-Bromophenyl)-1-phenyl-1H-benzoimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NITTO DENKO CORPORATION; ZHENG, Shijun; CAYAS, Jensen; LI, Sheng; MOCHIZUKI, Amane; CHAF, Hyunsik; HARDING, Brett, T.; WO2011/8560; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 33543-78-1, 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. 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Imidazole-2-carboxylic acid ethyl ester 1 (100 mg, 0.71 mmol) was dissolved in 10 ml of THF, sodium hydride (43 mg, 1.78 mmol) was slowly added under an ice bath for activation for 1 h, and iodomethane (507 mg, 3.57 mmol) was added,After the addition, the reaction was performed at room temperature for 1h. TLC detection reaction is complete,Stop the reaction,Concentrate under reduced pressure to remove the solvent,Add water to dissolve,Ethyl acetate extraction (3×20ml),Combine organic layers,Wash with saturated saline,Dry over anhydrous sodium sulfate and filter,Concentrate to get crude product.Purified by column chromatography (PE:EA=1:1) to obtain yellow oily liquid,Compound 1-methyl-1H-imidazole-2-carboxylic acid ethyl ester 1b(98 mg, yield 89%).

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 1H-imidazole-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sichuan University; Li Guobo; Wang Zhenling; (40 pag.)CN111187218; (2020); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 89830-98-8, name is 5-Cyclopropyl-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 89830-98-8, Quality Control of 5-Cyclopropyl-1H-imidazole

[00400] A mixture of Example 61f (300 mg, 0.63 mmol), Example 61g (204 mg, 1.89 mmol), 8- quinoline (36 mg, 0.25 mmol), Cs2C03(411 mg, 1.26 mmol) and Cu20 (36 mg, 0.25 mmol)in BuCN (5 mL) was stirred at 120°C for 16 h under N2. Then the solution was filtrated and purified by Prep-HPLC, followed by Prep-TLC (DCM/MeOH= 20/1) to give thedesired product Example 61 (6.6 mg, yield 2percent) as a white solid. LCMS [M+l] + = 456.0. NMR (400 MHz, DMSO- 6) delta 11.25 (s, 1H), 8.67 (s, 1H), 8.04 (t, J= 7.9 Hz, 1H), 7.85 (t, J= 7.0 Hz, 2H), 7.76 (s, 1H), 7.62 (s, 1H), 7.34 (s, 1H), 7.10 (s, 1H), 4.37 (m, 2H), 4.25 (t, J= 8.5 Hz, 2H), 2.47 (m, 2H), 2.19 (s, 3H), 1.96 (m, 2H), 1.82 (m, 1H), 0.82-0.73 (m, 2H), 0.69 (d, J= 4.4 Hz, 2H).

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, 5-Cyclopropyl-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FRONTHERA U.S. PHARMACEUTICALS LLC; JIN, Bohan; DONG, Qing; HUNG, Gene; (214 pag.)WO2019/51265; (2019); 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 51605-32-4 as follows. COA of Formula: C7H10N2O2

(5-Methylimidazol-4-yl)methylchloride hydrochloride (14) A paste of ethyl 4-methyl-5-imidazolecarboxylate (37.5 g, 0.243 mol) and a little dry THF was added in portions to a stirred suspension of LiAlH4 (12.0 g, 0.316 mol) in 1.0 L of dry THF under a flow of nitrogen. After refluxing for 4 h, the suspension was cooled in an ice-water bath and the excess LiAlH4 destroyed with successive additions of 12 mL of H2 O, 12 mL of 15percent NaOH, and 45 mL of H2 O. The white suspension was brought to room temperature (2 h) and filtered. After collecting the precipitate, it was digested in hot THF (500 mL), cooled, and filtered again. The total THF filtrate was concentrated in vacuo, the residual orange oil was dissolved in a minimum amount of EtOH, and 500 mL of hot EtOAc:Et2 O (3:2) was added. The solution was chilled yielding 15.0 g (55percent) of (5-methylimidazol-4-yl)methanol as white prisms: mp 138° (lit. 138°). This material (9.6 g, 0.086 mol) was dissolved in 50 mL of conc HCl and heated on a steam bath for 30 min. The acidic mixture was concentrated in vacuo to dryness and the solid dissolved in a minimum amount of EtOH. With the addition of a little dry Et2 O, 14 (8.5 g, 67percent) precipitated as a white powder: mp 236°-237° (lit. 222°).

According to the analysis of related databases, 51605-32-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Research Corporation; US4432983; (1984); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 870837-70-0, name is 4-(1H-Imidazol-1-yl)-3-methoxybenzaldehyde, 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 870837-70-0, category: imidazoles-derivatives

Cyano ethyl acetate (76.0 muL) and piperidine were added one by one to an ethanol solution (5.0 mL) of 4-(1H-imidazol-1-yl-3-methoxybenzaldehyde (144 mg) obtained in Example 111 (35.0 muL). The reaction solution was refluxed for 3.5 hours, water and ethyl acetate were added to the reaction solution, and the organic layer was partitioned. After the obtained organic layer was washed with a saturated saline solution, it was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain the crude ester product

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; Eisai Co., Ltd.; US2006/4013; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 705-09-9,Some common heterocyclic compound, 705-09-9, name is 2-(Difluoromethyl)-1H-benzo[d]imidazole, molecular formula is C8H6F2N2, 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) 0.84 g (5 mmol) of 2-difluoromethylbenzimidazole dissolved in DMF (25 ml) was added and reacted with 60% sodium hydride (0.24 g, 6 mmol) at room temperature for 30 minutes. This suspension was added to a solution of 2,4,6-trichloropyrimidine (0.92 g, 5 mmol) dissolved in DMF (25 ml) and stirred at room temperature for 1.5 hours. The reaction solution was poured into water and the resulting precipitates were recrystallized from methanol to obtain 0.98 g (yield: 62%) of 4,6-dichloro-2-(2-difluoromethylbenzimidazol-1-yl)pyrimidine.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(Difluoromethyl)-1H-benzo[d]imidazole, its application will become more common.

Reference:
Patent; ZENYAKU KOGYO KABUSHIKI KAISHA; EP1389617; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 104619-51-4,Some common heterocyclic compound, 104619-51-4, name is Di(1H-imidazol-1-yl)methanimine, molecular formula is C7H7N5, 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 solution containing the product from step 1 (8.36g, 54.2 mmol) and 2-amino-4- nitrophenol (8.74g, 54.2 mmol) in anhydrous THF (200 mL) was allowed to reflux under N2 for 14 hours. The mixture was cooled to RT, filtered, and the precipitate was washed with THF (cold) then dried in vacuo to afford the desired product (9.Og), as a yellow solid. MS (ESI) m/e (M+H4): 180. 1H NMR (DMSO) delta: 7.85 ~ 7.96(m, 3 H), 7.52(d, J = 8.8 Hz, 1H).

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

Reference:
Patent; MERCK SHARP &; DOHME CORP.; COBURN, Craig, A.; MCCAULEY, John, A.; LUDMERER, Steven, W.; LIU, Kun; VACCA, Joseph, P.; WU, Hao; HU, Bin; SOLL, Richard; SUN, Fei; WANG, Xinghai; YAN, Man; ZHANG, Chengren; ZHENG, Mingwei; ZHONG, Bin; ZHU, Jian; WO2010/111483; (2010); 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. 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, A new synthetic method of this compound is introduced below., Application In Synthesis of Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate

(1) potassium carbonate K2CO3 , AMST-1 C12H20N2O3 , AMST-2 C33H25BrN4 , In acetonitrile is added to the reaction kettle, raising the temperature to 80 C, keeps reaction for 3 hours, HPLC monitoring reaction, after the completion of reaction of outer 95 C distilling acetonitrile, lowering the temperature to 0 C stirring 8 hours, filtration products, the filter cake is acetonitrile leaching, after drying, the crude product in water for 3 C beating 5 hours to remove the inorganic salt, filtered, washed with water, 90 C drying to constant weight to obtain the product AMST – 3 C45 H44 N6 O3 ; K the potassium carbonate2 CO3 , AMST-1 C12H20N2O3 , AMST-2 C33H25BrN4 , Acetonitrile and water mass ratio of the 173:150: 383:2000: 1600;

The synthetic route of 144689-93-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangxi Yong Tong Technology Co., Ltd.; Liu Zhongchun; (10 pag.)CN107311989; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem