Month: March 2021

Application of 53439-88-6,Some common heterocyclic compound, 53439-88-6, name is 5-Amino-1,3-dimethyl-1H-benzo[d]imidazol-2(3H)-one, molecular formula is C9H11N3O, 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.

General procedure: A mixture of aniline (19d-e) (13.0 mmol), ethyl chloroformate (2.5 mL, 26.0 mmol) and Et3N (3.6 mL, 26.0 mmol) in anhydrous THF (150 mL) was stirred at room temperature for 30 min. The solid was filtered off and the solvent was evaporated under reduced pressure. The residue was dissolved in CH2Cl2 (100 mL) and the organic layer was washed with water (3 ¡Á 50mL). The organic phase was evaporated under reduced pressure to give 20d-e in quantitative yield (98%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Amino-1,3-dimethyl-1H-benzo[d]imidazol-2(3H)-one, its application will become more common.

Reference:
Article; Conconi, Maria Teresa; Marzaro, Giovanni; Urbani, Luca; Zanusso, Ilenia; Di Liddo, Rosa; Castagliuolo, Ignazio; Brun, Paola; Tonus, Francesca; Ferrarese, Alessandro; Guiotto, Adriano; Chilin, Adriana; European Journal of Medicinal Chemistry; vol. 67; (2013); p. 373 – 383;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 857035-29-1, 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. 857035-29-1, name is Ethyl 2-chloro-1H-benzo[d]imidazole-6-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

LiAlH4 (0. 146 mol) was added portion wise to a solution of tetrahydrofuran (200 ml) at 5C under N2 flow. A solution of b-1 (0.073 mol) in tetrahydrofuran (200 ml) was then added drop wise. The mixture was stirred at 5C for 3 hours. A minimum of H20 was then added, followed by a solution of CH2Cl2/CH30H (90/10). The resulting mixture was dried (over MgSO4), filtered and the solvent was evaporated until dryness, yielding 12.6 g of intermediate b-2 (95%, melting point: 179C).

The synthetic route of Ethyl 2-chloro-1H-benzo[d]imidazole-6-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD.; WO2005/58871; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 221289-88-9, 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. 221289-88-9, name is 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows.

A solution of 3,4-diaminobenzonitrile (2.60 g, 18.2 mmol) and pyridine (2 mL, 25 mmol) in DMF (20 mL) was added a solution of bis(trichloromethyl)carbonate (2.12 g, 7.14 mmol) in tetrahydrofuran (20 mL) dropwise under ice-cooling. The mixture was stirred at room temperature for 18 h. Dilute hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with brine, dried and concentrated under reduced pressure. To the residue was added ethyl acetate, and then the precipitate was collected by filtration to give 2-hydroxybenzimidazole-5-carbonitrile (896 mg, 29%) as a purple solid. A mixture of the above compound (894 mg, 5.62 mmol) and phosphorus oxychloride (12 mL) was refluxed for 3 h. The reaction mixture was added to ice, and extracted with ethyl acetate. The extract was washed with brine, dried and concentrated under reduced pressure. The residue was purified by silica gel chromatography with n-hexane/ethyl acetate (2:3, v/v) to give the title compound (322 mg, 32%) as a white powder. LC-MS (ESI) m/z 178.0 [M+H]+.

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

Reference:
Article; Yoshida, Tomohiro; Akahoshi, Fumihiko; Sakashita, Hiroshi; Sonda, Shuji; Takeuchi, Masahiro; Tanaka, Yoshihito; Nabeno, Mika; Kishida, Hiroyuki; Miyaguchi, Ikuko; Hayashi, Yoshiharu; Bioorganic and Medicinal Chemistry; vol. 20; 16; (2012); p. 5033 – 5041;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 23785-21-9, 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. 23785-21-9, name is Ethyl 1H-imidazole-4-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Ste -2: (0913) Preparation of ethyl 1-amino-1H-imidazole-5-carboxylate: (0914) [00346] To stirred solution of ethyl 1H-imidazole-5-carboxylate (0.1 g, 0.71 mmol) in N,N-dimethylformamide (10 mL) cooled to -10 C, was added lithium bis(trimethylsilyl)amide (0.78 mL, 0.78 mmol) drop wise and the reaction mixture was stirred at -10 C for 15 min. Then (aminooxy)diphenylphosphine oxide (0.199 g, 0.85 mmol) was added at -10 C and the reaction mixture was stirred at room temperature for 6 h. The reaction mixture was quenched by slow addition of water until the precipitate formed was dissolved to become clear solution. Then it was extracted using ethyl acetate (2 x 50 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to afford the title compound ethyl 1- amino-1H-imidazole-5-carboxylate as off white solid (0.1 g, crude). Calculated (M+H): 156.07; Found (M+H): 156.1.

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

Reference:
Patent; LUC THERAPEUTICS; ANDERSON, David, R.; VOLKMANN, Robert, A.; MENNITE, Frank, S.; FANGER, Christopher; (390 pag.)WO2017/100591; (2017); 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. 401567-00-8, name is 2-Chloro-1H-benzo[d]imidazole-5-carbonitrile, A new synthetic method of this compound is introduced below., name: 2-Chloro-1H-benzo[d]imidazole-5-carbonitrile

General procedure: 4.1.6. General procedure E: removal of SEM group To a solution of SEM-protected compound (1.0 equiv) in THFwas added TBAF (3.0 equiv, 1 M in THF). The mixture was reuxedfor 11-20 h, then cooled to room temperature, and concentratedunder reduced pressure. The residue was puried by silica gel col-umn chromatography or PTLC to afford the product.

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:
Article; Okazaki, Shogo; Noguchi-Yachide, Tomomi; Sakai, Taki; Ishikawa, Minoru; Makishima, Makoto; Hashimoto, Yuichi; Yamaguchi, Takao; Bioorganic and Medicinal Chemistry; vol. 24; 21; (2016); p. 5258 – 5269;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 137049-00-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 137049-00-4 name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

0.07 g (0.21 mmol) of (R,3r)-3-((7S,8R)-7-(azetidin-1-yl)-8-benzyl-5,6,7,8-tetrahydronaphthalen-2-yl)cyclobutanamine were dissolved in dichloromethane, 0.05 g (0.41 mmol) dimethylaminopyridine were added, followed by 0.04 g (0.21 mmol) of 1-methyl-1H-imidazole-4-sulfonyl chloride. The mixture was stirred at room temperature overnight. The reaction mixture was evaporated and the residue was partitioned between ethyl acetate and aqueous bicarbonate solution. The aqueous phase was discarded and the organic phase was washed again with aqueous bicarbonate solution, then twice with aqueous ammoniumchloride solution (10%). The organic phase was dried over MgSO4 and evaporated to dryness. The desired product was obtained as a light brown resin (0.01 g, 0.01 mmol, 7%). ESI-MS [M+H+]=491 Calculated for C28H34N4O2S=490.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Methyl-1H-imidazole-4-sulfonyl chloride, and friends who are interested can also refer to it.

Reference:
Patent; Amberg, Wilhelm; Pohlki, Frauke; Lange, Udo; Wang, Ying; Brewer, Jason; Vasudevan, Anil; Lao, Yanbin; Hutchins, Charles; Zhao, Hongyu; Li, Huan-Qiu; US2015/111875; (2015); 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. 72-40-2, name is 5-Amino-1H-imidazole-4-carboxamide hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 5-Amino-1H-imidazole-4-carboxamide hydrochloride

4-amino-5-imidazolecarboxamide hydrochloride was heated to reflux in phosphorus oxychloride for 3.5hs and after purification gave 4-amino-5-nitrile imidazole. This was resuspended in ethanol saturated with HCl overnight and purification gave 4-amino-5-ethylimino ester imidazole hydrochloride. This was combined with diphenylborinic acid ethanolamine ester in tetrahydrofuran (THF) overnight to yield the title compound.

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 72-40-2.

Reference:
Patent; The Penn State Research Foundation; EP1420021; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 17286-47-4, 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. 17286-47-4, name is 2-(1H-Imidazol-2-yl)ethanamine dihydrochloride, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 4-bromo-lH-pyrrolo[2,3-b]pyridine-2-carboxylic acid(200 mg, 0.830 mmol) in DMF (15 mL) was added hydroxybenzotriazole (HOBt) (224 mg, 1.66 mmol), EDOHC1 (318 mg, 1.66 mmol), TEA (420 mg, 4.15 mmol, 0.58m), the reaction mixture was stirred at 50 C for 0.5 hour, then added 2-(lH-imidazol-2-yl) ethanamine (305 mg, 1.66 mmol, 2 HC1 salt) into it and continued stirred for another 2.5 h to give a pale yellow suspension. LCMS showed the purity of the desired product (Rt = 0.600 min; MS Calc?d: 333.0; MS Found: 333.9 [M+H]+). The mixture was diluted with water (15 mL), then extracted with EtOAc (20 mL x2), the combined extracts was washed with brine (25 mL x2), dried over Na2S04, filtered and concentrated under reduced pressure to give N-(2-(lH-imidazol-2- yl)ethyl)-4-bromo-lH-pynOlo[2,3-b]pyridine-2-carboxamide (250 mg, purity: 92%, yield: 83%) as an off-white solid NMR (400 MHz, DMSO-r e) d 2.86-2.95 (2H, m), 3.52-3.65 (2H, m), 6.85-6.98 (2H, m), 7.15 (1H, s), 7.42 (1H, d, J= 5.2 Hz), 8.19 (1H, d, J= 4.8 Hz), 8.83 (1H, br s), 11.82 (1H, br s), 12.56 (1H, br s).

The chemical industry reduces the impact on the environment during synthesis 2-(1H-Imidazol-2-yl)ethanamine dihydrochloride. I believe this compound will play a more active role in future production and life.

Reference:
Patent; PETRA PHARMA CORPORATION; KESICKI, Edward A.; RAVI, Kannan Karukurichi; LINDSTROeM, Johan; PERSSON, Lars Boukharta; LIVENDAHL, Madeleine; VIKLUND, Jenny; GINMAN, Tobias; FORSBLOM, Rickard; RAHM, Fredrik; HICKEY, Eugene R.; DAHLGREN, Markus K.; GERASYUTO, Aleksey I.; (478 pag.)WO2019/126733; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 32673-41-9,Some common heterocyclic compound, 32673-41-9, name is 4-Imidazolemethanol hydrochloride, molecular formula is C4H7ClN2O, 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.

Step 1 Preparation of 1-triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of 4-(hydroxymethyl)imidazole hydrochloride (35 g) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which was sufficiently pure for use in the next step.

The synthetic route of 32673-41-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US5710171; (1998); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 25676-75-9, name is 4-Bromo-1-methylimidazole, 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 25676-75-9, Product Details of 25676-75-9

c) To a dry, N2 purged, 500 mL three neck flask equipped with a stir bar is added 200 mL of dry diethyl ether and 4-bromo-N-methylimidazole (50.0 g, 311 mmol). The flask is then cooled to -10 C. with an acetone/ice bath. A 2.0 M heptane/THF/ethylbenzene solution of lithium diisopropylamide (171 mL, 342 mmol) is then added via syringe while maintaining the reaction temperature at 0 C. or lower. After 1 hour, dimethylformamide (DMF) (36.1 mL, 466 mmol) is added dropwise over 5 minutes. The reaction mixture is allowed to stir for 45 minutes at or below 5 C. and then quenched with a saturated aqueous solution of citric acid. The resulting mixture is stirred vigorously until the two phases separate. The organic layer is recovered and washed (3*200 mL) with water. The solvent is removed in vacuo to give the desired product, 2-formyl-4-bromo-(1) N-methylimidazole, as a brown crystalline solid (yield: 55.7 g, 95 percent, 86 percent purity by GC). Additional purification may be achieved by elution through alumina using methylene chloride solvent.

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, 4-Bromo-1-methylimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Vosejpka, Paul C.; Boone, Harold W.; Frazier, Kevin A.; Iverson, Carl N.; US2009/69567; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem