Category: imidazoles-derivatives

Related Products of 10364-94-0, 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. 10364-94-0, name is (1H-Imidazol-1-yl)(phenyl)methanone belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of substrate (100 mg) in 2.5 mL MeCN (dry) was added DBU (0.2 equiv.), and themixture was allowed to stir at 50 C for 10 min. 1-Benzoylimidazole (1.1 equiv.) in MeCN (dry, 0.5 mL)was added to the reaction mixture in two portions and it was allowed to stir at 50 C for 8 h. MeCNwas removed under reduced pressure and the resulting mixture was purified by flash columnchromatography (ethyl acetate/petroleum ether = 1:6 to 2:1) to afford benzoylated products.

The synthetic route of (1H-Imidazol-1-yl)(phenyl)methanone has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lu, Yuchao; Hou, Chenxi; Ren, Jingli; Xin, Xiaoting; Xu, Hengfu; Pei, Yuxin; Dong, Hai; Pei, Zhichao; Molecules; vol. 21; 5; (2016);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 14741-71-0, The chemical industry reduces the impact on the environment during synthesis 14741-71-0, name is Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate, I believe this compound will play a more active role in future production and life.

2.00 g (9.79 mmol) of ethyl (2-benzimidazolyl)acetate was added to a mixture of 1.83ml (19.6mmol) of phosphoryl chloride and 2.28 ml (29.4 mmol) of N,N-dimethylformamide at 0C, and the resulting mixture was heated at 95C for 50 minutes. After cooling, 50 ml of ice-water was added thereto, and potassium carbonate was added to this mixture until it became alkaline, and then this was extracted with chloroform (100 ml x 3). The chloroform layers were combined and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was washed with ethyl acetate and taken out through filtration to obtain a dark brown crystal. Butyric anhydride (10 ml) suspension of the dark brown crystal synthesized above was heated at 170C for 70 minutes. After cooling, the solvent was evaporated under reducedpressure, and the residue was washed with diisopropyl ether and taken out through fil tration to obtain 713 mg (26%) of the entitled compound (I-80) as an orange crystal. MS(EI)m/z:285(M+).1H-NMR(40OMHz, DMSO-d6)delta: 1.16(3H, t, J=7.33Hz), 1.34(3H, t, J=7.08Hz), 2.45-2.60(2H, m), 4.34(2H, q, J=7.08Hz), 7.31-7.39(1H, m), 7.48-7.53(1H, m), 7.68(1H, d, J=7.81Hz), 7.85(1H, s), 8.67(1H, d, J=7.81Hz). IR(ATR): 3203, 1685, 1637, 1606, 1552, 1462, 1369, 1323, 1240, 1182, 1134, 1107, 1090 cm-1.

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 2-(1H-benzo[d]imidazol-2-yl)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1479681; (2004); 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. 4856-97-7, name is (1H-Benzoimidazol-2-yl)methanol, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H8N2O

To a three-necked flask was added 1.24 g (6 mmol) of dicyclohexylcarbodiimide, 0.12 g (lmmol) of 4-dimethylaminopyridine, followed by addition of 25 mL of tetrahydrofuran, After stirring and dissolving, Adding 1. 03 g (5 mmol) of 5-nitroindol-3-carboxylic acid, After stirring for half an hour at room temperature, 0.75 g (5 mmol) of 2-light methylbenzimidazole was added and stirred at room temperature for 8 h to stop the reaction. The reaction was filtered, the filtrate was distilled, dried and dissolved in dichloro Methane, standing at room temperature until a large amount of precipitate precipitated, filtered, washed with water, dried in vacuo to give 1.28g (1H-benzimidazol-2-yl) methyl-5-nitro-1H-indole-3-carboxylate in a yield of 76. 19percent.

According to the analysis of related databases, 4856-97-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Qingdao University of Science & Technology; Kang, Congmin; Wang, XinYing; Liu, yizhou; (5 pag.)CN105315262; (2016); A;,
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. category: imidazoles-derivatives

(1) the addition of water in the reactor 10 kg, the previous batch filtrate 8 kg (filtrate all recovery use, so there is no discharge), imidazole 2.6 kg, potassium hydroxide 3.9 kg, batchwise by adding bromine 4.8 kg, canada finishes, controlled to disappear in the raw materials, the reaction temperature is controlled in the 80 – 90 C). Adding concentrated hydrochloric acid to adjust the pH to 7 the left and right, a large quantity of solid precipitate (mostly 4 – bromo – 1H – imidazole and a little double bromine substituted imidazole). Filtering after-filtration cake (4.3 kg, yield 90%) can be directly into the next step of the reaction, the filtrate as the solvent directly used in the next batch (non-sewage disposal).

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; Hangzhou Lide Biological Technology Co., Ltd.; Ren Guobao; Wu Yan; Li Chuanbin; (5 pag.)CN106674121; (2017); A;,
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 18075-64-4 as follows. SDS of cas: 18075-64-4

Example 151 1-Phenyl-1H-imidazole-4-carboxylic acid {2-oxo-2-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethyl}-amide DIPEA (186 mg, 1.4 mmol) was added to a stirred solution of 1-phenyl-1H-imidazole-4-carboxylic acid (60 mg, 0.32 mmol) in DMF (5 mL) followed by HOBt (47 mg, 0.35 mmol) and EDCI (153 mg, 0.8 mmol). After 2 minutes of stirring, 2-amino-1-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethanone hydrochloride (119 mg, 0.35 mmol) (prepared according to Step 1 and 5 of the General Scheme) was added and the resulting mixture was stirred at ambient temperature overnight. The reaction mixture was diluted with cold water, the solid was collected to afford the 129 mg (86% Yield) of 1-phenyl-1H-imidazole-4-carboxylic acid {2-oxo-2-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethyl}-amide. LC/MS [M+H]+: Purity: 473 (M+1), 96.61%. 1H NMR (300 MHz, DMSO-d6): delta 8.4 (s, 1H), 8.32 (s, 1H), 8.08 (t, 1H), 7.8 (d, 2H), 7.6-7.48 (t, 3H), 7.46 (t, 1H), 7.36-7.24 (t, 3H), 4.9 (s, 1H), 4.2 (d, 2H), 4.0 (bs, 1H), 3.8 (bs, 1H), 3.5 (d, 2H), 2.1 (t, 2H), 1.8 (d, 2H).

According to the analysis of related databases, 18075-64-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Forest Laboratories Holdings Limited; US2009/239810; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 918321-20-7, These common heterocyclic compound, 918321-20-7, name is Methyl 5-amino-4-fluoro-1-methyl-1H-benzo[d]imidazole-6-carboxylate, 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 an inertized (N2) reaction vessel at internal temperature 20C and under exclusion of humidity and air, Compound 1 (1.0 eq.) and Compound 2 (1.2 eq.) are reacted in the presence of cesium carbonate (2.4 eq.), tris(dibenzylidenaceton) dipalladium(O) (0.035 eq.) and Xantphos (0.07 eq.) in a mixture of toluene and 1 ,4-dioxane at internal temperature of 99C. After 8 hours, the mixture is cooled to internal temperature of 60C. Subsequently, dimethylformamide (DMF), filter aid (CEFOK) and activated charcoal (EKNS) are added, and the mixture is stirred and cooled to internal temperature of 35 C. The solids are filtered off and washed with a mixture of dimethylformamide and toluene. To the filtrate, which contains the product Compound 3, is introduced at internal temperature of25 C hydrogen chloride gas (CLC) whereupon the HQ salt of Compound 3 crystallizes. The palladium residue mainly remains in solution. After warming to 60 C and cooling to 0C, the solids are filtered using a centrifuge and are washed with a mixture of toluene and dimethylformamide. The damp Compound 3 HC1 salt is charged to a reactor (equipped with pH probe) together with dimethylformamide and is heated to 60C. By adding a 4 wt% of aqueous tripotassium phosphate solution, the pH is adjusted to a pH range of 6.8-7.6 (with a target of pH 7.2) while Compound 3 crystallizes as free base. After cooling to 22C and stirring, the solids are filtered using a centrifuge and are washed with drinking water. The moist solids are dried at 50 C under vacuum to give dry, crude Compound 3. In order to remove residual palladium, dry, crude Compound 3 is dissolved in dimethylformamide at internal temperature of 60C and stirred together with Smopex-234 (commercially available from Johnson Matthey) and activated charcoal for 90 minutes. The solids are filtered off at internal temperature of 60C and are washed with dimethylformamide. To the filtrate are added drinking water and Compound 3 seed crystals. More drinking water is added while Compound 3 crystallizes. After cooling to internal temperature of 20 C, the solids are filtered using a centrifuge and are washed with a mixture of deionized water and dimethylformamide and with deionized water. The moist solids are dried at 50C under vacuum, providing 6-(4-Bromo-2-fluorophenylamino)-7-fluoro-3- methyl-3H-benzoimidazole-5-carboxylic acid methyl ester (Compound 3).

The synthetic route of 918321-20-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; ARRAY BIOPHARMA INC.; KRELL, Christoph, Max; MISUN, Marian; NIEDERER, Daniel, Andreas; PACHINGER, Werner, Heinz; WOLF, Marie-christine; ZIMMERMANN, Daniel; LIU, Weidong; STENGEL, Peter, J.; NICHOLS, Paul; WO2014/63024; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 139481-44-0,Some common heterocyclic compound, 139481-44-0, name is Methyl 1-((2′-cyano-[1,1′-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate, molecular formula is C25H21N3O3, 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 four-neck flask, 20 g of Compound 1 was added, and while stirring, 100 mL of dimethyl sulfoxide solution in which 10.14 g (3 eq) of hydroxylamine hydrochloride was added was added, and the mixture was heated to 90 DEG C and 30.95 g (6 eq) was added in portions under stirring. Sodium carbonate, after the completion of the reaction for 9-10 hours, after the completion of the reaction, it is allowed to come to room temperature, and 100 mL of water is added to stir the mixture. The solid precipitates, which is cooled down to 0-5C. Stirring is continued for about 1 hour, and the mixture is dried by suction to obtain 15.2 g of compound 2. The yield was 70.4%.

The synthetic route of 139481-44-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Disha Pharmaceutical Group Co., Ltd.; Fu Kaimin; (7 pag.)CN103242305; (2018); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 2034-22-2, name is 2,4,5-Tribromoimidazole, molecular formula is C3HBr3N2, 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: 2034-22-2

PRODUCTION EXAMPLE 3 [PRODUCTION OF THE PRESENT COMPOUND (3)] To a solution of a sodium salt, prepared from 1.22 g of 2,4,5-tribromoimidazole and 0.16 g of 60% oil-based sodium hydride, in 5 ml of N,N-dimethylformamide was added dropwise 1.23 g of 4-bromobutoxymethyl bromide at room temperature. After stirring at room temperature for 3 hours, 50 ml of water was added to the reaction mixture which was then extracted with three 30-ml portions of ether. The ether layer was dried over magnesium sulfate and concentrated. The oily product obtained was purified by column chromatography on silica gel to obtain 0.74 g of 1-(4-bromobutoxymethyl)-2,4,5-tribromoimidazole.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2034-22-2, its application will become more common.

Reference:
Patent; Sumitomo Chemical Company, Limited; US4689340; (1987); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 51605-32-4, These common heterocyclic compound, 51605-32-4, name is Ethyl 5-methyl-1H-imidazole-4-carboxylate, 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.

A. To a stirred suspension of ethyl 4-methyl-1H-imidazole-5-carboxylate (2.00 g, 13.0 mmol) in acetonitrile (25 mL) and chloroform (25 mL) was added N-bromosuccinimide (2.31 g, 13.0 mmol). The reaction mixture was stirred under nitrogen atmosphere for 20 h, then concentrated in vacuo. The residue was dissolved in ethyl acetate (100 mL) and washed with saturated aqueous sodium bicarbonate (50 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluding with 50percent ethyl acetate in hexanes to afford ethyl 2-bromo-4-methyl-1H-imidazole-5-carboxylate as a light yellow solid (1.88 g, 62percent): 1H NMR (300 MHz, CDCl3) delta 4.35 (q, J=7.1 Hz, 2H), 2.51 (s, 3H), 1.37 (t, J=7.1 Hz, 3H); MS (ES+) m/z 233.1 (M+1), 235.1 (M+1).

The synthetic route of 51605-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dales, Natalie; Fonarev, Julia; Fu, Jianmin; Hou, Duanjie; Kamboj, Rajender; Kodumuru, Vishnumurthy; Pokrovskaia, Natalia; Raina, Vandna; Sun, Shaoyi; Zhang, Zaihui; US2009/156615; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 46006-36-4, 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 46006-36-4 as follows.

3H-Benzoimidazole-4-carboxylic acid[3-(1H-tetrazol-5-yl)-phenyl]-amide (16) 3-(1H-Tetrazol-5-yl)aniline (75 mg, 0.47 mmol), 1H-benzimidazole-4-carboxylic acid (76 mg, 0.47 mmol), 1-ethyl-3-[3-dimethylaminopropyl]carbodiimide hydrochloride (135 mg, 0.7 mmol), 1-hydroxybenzotriazole (95 mg, 0.7 mmol) and N,N’-diisopropylethylamine (0.17 mL, 0.94 mmol) was stirred in DMF (0.5 mL) at room temperature for 24 h. The reaction mixture is diluted with water (2 mL) and after approximately adjusting the pH to 4 with 1N HCl, the mixture was extracted with ethyl acetate. The organic extracts were washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. The crude material was purified by reverse phase HPLC to afford the product as a trifluoroacetic acid salt in 5% yield. 1H NMR (DMSO-d6) delta 8.62 (s, 1H), 8.53 (s, 1H), 7.99-8.02 (m, 3H), 7.86 (d, J=8 Hz, 1H), 7.77 (d, J=4 Hz, 1H), 7.62 (t, J=8 Hz, 1H), 7.43 (t, J=8 Hz, 1H), 7.04 (s, 1H); LCMS (ESI) m/z 306 (MH+).

According to the analysis of related databases, 46006-36-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITY OF SOUTH FLORIDA; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; Chen, Yu; Nichols, Derek; Renslo, Adam R.; Jaishankar, Priyadarshini; Lauterwasser, Erica M. W.; (29 pag.)US9556131; (2017); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem