Author: Jessica.F

Adding a certain compound to certain chemical reactions, such as: 693-98-1, name is 2-Methyl-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 693-98-1, HPLC of Formula: C4H6N2

General procedure: Aryl halide (1.0mmol), amine (1.5?2.0mmol), PNP-SSS (0.6molpercent; 0.023g), K2CO3 (2mmol), and DMF (3.0mL) was placed in a 25mL flask equipped with a magnetic stirring bar and heated at 120°C under nitrogen gas. The reaction was then monitored by TLC until the consumption of aryl halide was detected. After completion of the reaction 5mL of water and 5mL of ethyl acetate were added to the reaction mixture. The organic solution was extracted and dried over anhydrous Na2SO4. After removing of organic solvent the crude product was obtained. For further purification the chromatography technique was used.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Methyl-1H-imidazole, and friends who are interested can also refer to it.

Reference:
Article; Panahi, Farhad; Daneshgar, Fatemeh; Haghighi, Fatemeh; Khalafi-Nezhad, Ali; Journal of Organometallic Chemistry; vol. 851; (2017); p. 210 – 217;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 6775-40-2, These common heterocyclic compound, 6775-40-2, name is 5-Phenyl-1H-imidazol-2-amine, 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.

General procedure: A mixture of the corresponding 2-amino-4-arylimidazole1 (1.0 mmol), aromatic aldehyde 2 (2.0 mmol) andmalononitrile 12 (1.0 mmol) in 2 mL of 2-propanol was refluxedduring 20-30 min. After cooling, the yellow solid products14 were filtered off and crystallized from iPrOH. 14a:yellow powder, 65%; mp 221-222 C; 1H NMR (200 MHz,DMSO-d6) delta 9.34 (s, 1H, CHazomethine), 8.18 (d, J = 7.3 Hz,2H, Ar), 7.68-7.48 (m, 7H, Ar, C5NH2 ), 7.31-7.10 (m, 8H,Ar), 5.34 (s, 1H, C7H); 13C NMR (125 MHz, DMSO-d6) delta162.4 (3), 149.5 (Cazomethine), 143.8 (C5), 138.3, 135.3, 133.3,133.0, 132.5, 132.1, 130.4, 129.5, 129.4, 128.8, 128.2, 128.1,127.4, 125.8, 117.9 (N), 71.7 (C6), 45.01 (C7); MS (m/z) (%):429 ([M+?], 25), 285 (100), 194 (19), 104 (26), 77 (19), 43 (25);anal. calcd for C28H23N5 (429.53) C, 78.30; H, 5.40; N, 16.31;found: C, 80.25; H, 5.70; N, 13.41.

The synthetic route of 6775-40-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lipson, Victoria V.; Pavlovska, Tetiana L.; Svetlichnaya, Nataliya V.; Poryvai, Anna A.; Gorobets, Nikolay Yu.; Van Der Eycken, Erik V.; Konovalova, Irina S.; Shiskina, Svetlana V.; Borisov, Alexander V.; Musatov, Vladimir I.; Mazepa, Alexander V.; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1032 – 1045;,
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. 71759-89-2, name is 5-Iodo-1H-imidazole, A new synthetic method of this compound is introduced below., Product Details of 71759-89-2

4-iodo-1H-imidazole (Compound 13, manufactured by Wako Pure Chemical Industries, Ltd.) (1.9 g, 10 mmol) was dissolved in dichloromethane (40 mL)below freezing,Triethylamine (2.1 mL, 15 mmol),Trityl chloride (3.4 g, 12 mmol) was added,Under an argon gas atmosphere,And the mixture was stirred at room temperature (25 C.) for 17 hours.After completion of the reaction,Add water,Extraction was carried out twice with dichloromethane.The combined dichloromethane layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure,The obtained crude product was purified by silica gel column chromatography (eluent (volume ratio): chloroform / n-hexane = 1/1 ? chloroform) to obtain Compound 14 (4.1 g, 9.3 mmol, yield 93%).

The synthetic route of 71759-89-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NIHON MEDI-PHYSICS COMPANY LIMITED; KYOTO UNIVERSITY; OKUMURA, YUKI; IZAWA, AKIHIRO; AKAMA, KEI; KOBASHI, NOBUYA; ABE, TSUTOMU; SAJI, HIDEO; KIMURA, HIROYUKI; (27 pag.)JP2015/110563; (2015); 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. 87941-55-7, name is 4-Bromo-1-trityl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C22H17BrN2

Example 226: N-[3-(1H-imidazol-4-yl)phenyl]-1-oxo-2,3,4,5-tetrahyd][1,4]diazepino[1,2-a]indole-8-carboxamide Step 1: Synthesis of 3-(l-trityl-1H-imidazol-4-yl)aniline (3-Aminophenyl)boronic acid (1.0 g, 7.3 mmol), 4-bromo-1-trityl-1H-imidazole (2.8 g, 7.3 mmol), tri-i-butylphosphonium tetrafluoroborate (424 mg, 1.5 mmol) and KF (1.4 g, 24.1 mmol) are added into dry THF (20 mL) and argon is bubbled through the mixture for 10 min. Tris-(dibenzylideneacetone) dipalladium(O) (669 mg, 0.7 mmol) is added and the reaction mixture is sealed and heated at 60 C for 16 h. The solid is filtered and the filtrate is diluted with EtOAc (250 mL). The solution is washed with water (3×100 mL), brine (100 mL), dried (Na2S04) and concentrated. The crude material is purified by flash column chromatography using methanol in CH2C12 to afford the title compound (1.1 g, 36%).

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 87941-55-7.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOYER, Stephen, James; GAO, Donghong, Amy; GUO, Xin; KIRRANE, Thomas, Martin, Jr.; SARKO, Christopher, Ronald; SNOW, Roger, John; SOLEYMANZADEH, Fariba; ZHANG, Yunlong; WO2011/71716; (2011); 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 312-73-2 as follows. COA of Formula: C8H5F3N2

General procedure: In a typical experimental procedure, a dry, two-necked, 50 mL round bottomed flask was charged with 5 mL of dry MeCN, 1.0 mmol of benzimidazole derivatives and 1.0 mmol of NaH. The solution was stirred at room temperature for 30 min, then a solution of 2,2,2-trifluoro acetimidoyl chloride derivatives (1.0 mmol in 2 mL of dry MeCN) was added dropwise via a syringe. The mixture was stirred at room temperature appropriate time and then filtered. After removing the solvent under reduced pressure, the crude product was purified by preparative thin-layer chromatography on silica gel [eluent: n-hexane/EtOAC, 3:1] to give the products. The products obtained from 2-mercapto benzimidazole and 2-mercapto-1-methyl imidazole were purified by washing with n-hexane.

According to the analysis of related databases, 312-73-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Darehkordi, Ali; Rahmani, Fariba; Journal of Fluorine Chemistry; vol. 190; (2016); p. 41 – 47;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 17289-26-8,Some common heterocyclic compound, 17289-26-8, name is 1-Methyl-1H-imidazole-4-carbaldehyde, molecular formula is C5H6N2O, 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 sealed tube is charged with tert-butyl 4-(p-tolylsulfonylhydrazono)- piperidine-1-carboxylate (1284.79 mg; 3.50 mmol; 1 .10 eq.), CS2CO3 (1553.44 mg; 4.77 mmol; 1 .50 eq.). The tube is RM is sealed, purged with argone and then 1 ,4-dioxane (12.00 mL) and 1 -methyl-1 – -imidazole-4- carbaldehyde (350.00 mg; 3.18 mmol; 1.00 eqf.) are added. RM is heated at 1 10C for 48 h. After this time, the mixture is filtered through a Celite pad and then the solvent is evaporated. Crude product is purified by FCC (hexane/EtOAc; gradient) to afford 4-(1 -methyl-1 H-imidazole-4-carbonyl)- piperidine-1 -carboxylic acid tert-butyl ester (483.90 mg; yield 51.0 %; 98% by UPLC) as a beige solid

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Methyl-1H-imidazole-4-carbaldehyde, its application will become more common.

Reference:
Patent; SELVITA S.A.; FABRITIUS, Charles-Henry Robert Yves; NOWAK, Mateusz Oktawian; WIKLIK, Katarzyna Anna; SABINIARZ, Aleksandra Barbara; BIE?, Marcin Dominik; BUDA, Anna Ma?gorzata; GUZIK, Pawel Szczepan; JAKUBIEC, Krzysztof Roman; MACIUSZEK, Monika; KWIECI?SKA, Katarzyna; TOMCZYK, Mateusz Micha?; GA??ZOWSKI, Micha? Miko?aj; GONDELA, Andrzej; DUDEK, ?ukasz Piotr; (681 pag.)WO2016/180536; (2016); 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. 3034-41-1, name is 1-Methyl-4-nitroimidazole, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1-Methyl-4-nitroimidazole

2, 5-Dichloro-Lambda/-(l -methyl- lH-imidazol-4-yl)pyrimidin-4-amine l-Methyl-4-nitro-lH-imidazole (Intermediate 5, 500 mg, 3.93 mmol) was dissolved in ethanol (7.868 mL) and Pd/C (10 wt%, Degussa, 105 mg, 0.10 mmol) was added. The reaction mixture was subjected to 1 atm of hydrogen for 3 hours. The reaction mixture was filtered through Celite and 2,4,5-trichloropyrimidine (0.361 mL, 3.15 mmol) and TEA (1.097 mL, 7.87 mmol) were added. The reaction mixture was stirred overnight at rt. The reaction mixture was filtered providing the title compound as a pale yellow solid (538 mg). LCMS: 245 [M+Eta]+.

According to the analysis of related databases, 3034-41-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; ALMEIDA, Lynsie; CHUAQUI, Claudio, Edmundo; GUAN, Amy; IOANNIDIS, Stephanos; LAMB, Michelle; PENG, Bo; SU, Qibin; WO2010/20810; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 3012-80-4,Some common heterocyclic compound, 3012-80-4, name is 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde, molecular formula is C9H8N2O, 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: The equimolar aldehyde 3a?3d (1 mmol) and substituted phenylhydrazine 5a?5s (1 mmol) weremixed in CH3OH (10 mL) and stirred at room temperature [18]. After about 2 h, the reaction wascompleted (monitored by TLC). The residual crude was purified via silica gel column chromatogramusing a gradient mixture of petroleum ether and ethyl acetate to obtain the pure target compounds6a?6ai (in 45?80percent yield).

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

Reference:
Article; Wang, Xing; Chen, Yong-Fei; Yan, Wei; Cao, Ling-Ling; Ye, Yong-Hao; Molecules; vol. 21; 11; (2016);,
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. 106429-57-6, name is Methyl 2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 106429-57-6

(b) 2,3-Dihydro-2-oxo-5-hydroxymethyl-1H-benzimidazole (20b) 24.6 g (0.128 mol) of 20a are suspended in THF and stirred with 624.8 ml (0.768 mol) of DIBAL (20% strength solution in toluene) at -70 C. overnight in analogy to Example 1a. Yield: 16.2 g (77%). C8 H8 N2 O2 (164.2). NMR (DMSO): delta=4.48 (s, 2H), 5.12 (broad s, 1H), 6.91 (s, 2H), 6.98 (s, 1H), 10.61 (broad s, 2H) ppm.

According to the analysis of related databases, 106429-57-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bayer Aktiengesellschaft; US4748163; (1988); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 17325-26-7, 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. 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of methyl-1H-imidazole-4-carboxylate (10.37 g, 74.0 mmol) in acetonitrile (200 mL) was added 2,4-dichloro-5-methylpyrimidine (10 g, 61.7 mmol) and potassium carbonate (25.5 g, 185.2 mmol), and then the mixture was stirred at RT for 16 h under an inert atmosphere. The reaction mixture was quenched with water, and extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by gradient column chromatography using ethyl acetate in hexane as eluent to afford methyl 1-(2-chloro-5-methylpyrimidin-4-yl)-1H-imidazole-4-carboxylate as a white solid (11 g, 75%). 1HNMR (400 MHz, DMSO-d6): delta 8.88 (s, 1H), 8.38 (s, 2H), 3.80 (s, 3H), 2.41 (s, 3H). LC-MS exact mass calcd 252.04, found m/z 253.2 [M+1-1]+.

The chemical industry reduces the impact on the environment during synthesis Methyl 1H-imidazole-5-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Asana Biosciences, LLC; Venkatesan, Aranapakam M.; Thompson, Scott K.; Smith, Roger A.; Reddy, Sanjeeva P.; (166 pag.)US2016/362407; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem