Month: July 2021

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. 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, A new synthetic method of this compound is introduced below., Computed Properties of C5H6N2O2

d) 3-(7-Cyano-isothiochroman-4-yl)-3H-imidazole-4-carboxylic acid methyl ester; To a solution of 4-hydroxy-isothiochroman-7-carbonitrile (630 mg, 3.3 mmol) in THF (20 ml.) is added methyl 4-imidazolecarboxylate (CASNo. 17325-26-7, 460 mg, 3.6 mmol), and triphenylphosphine (909 mg, 3.4 mmol). The reaction is cooled to 0 0C and diisopropyl azodicarbpxylate (0.66 ml_, 3.4 mmol) is added. The reaction is permitted to warm to room temperature and stirred until LC-MS analysis indicates complete consumption of 4-hydroxy- isothiochroman-7-carbonitrile. The reaction mixture is diluted with saturated aqueous NaHCO3 and ethyl acetate. The layers are separated and the organic layer is dried with Na2SO4, filtered and concentrated. The resulting residue is purified by silica gel flash chromatography (ethyl acetate-dichloromethane, 0:1 to 1 :1) to provide 3-(7-cyano- isothiochroman-4-yl)-3H-imidazole-4-carboxylic acid methyl ester; MS: (ESI) m/z 300.1 (M+H). 1H NMR (400 MHz, CDCI3) delta ppm 3.08 – 3.23 (m, 1 H), 3.32 (dd, J=14.4, 4.0 Hz, 1 H), 3.73 – 4.07 (m, 2 H), 3.91 (s, 3 H)1 6.46 – 6.61 (m, 1 H), 7.15 (d, J=8.1 Hz, 1 H), 7.46 (s, 1 H), 7.49 – 7.54 (m, 1 H), 7.56 (s, 1 H), 7.84 (s, 1 H). The HCI salt of the title compound can be prepared by dissolution in diethyl ether followed by treatment with an excess of 1N HCI in diethyl ether. The resulting heterogeneous solution is concentrated to furnish the HCI salt of 3-(7-cyano-isothiochroman-4-yl)-3H-imidazole-4-carboxylic acid methyl ester.

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; NOVARTIS AG; WO2008/76336; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 16042-25-4, 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. 16042-25-4, name is 2-Imidazolecarboxylic acid belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

a) yV-o-Tolyl-1W-imidazole-2-carboxamideTo a solution of 1 /-/-imidazole-2-carboxylic acid (0.52 g, 4.64 mmol) in DMF (20 mL) was added o-toluidine (0.50 mL, 4.64 mmol), EDC-HCI (1.35 g, 6.96 mmol) and HOBt (0.94 g, 6.96 mmol). The reaction mixture was stirred at room temperature for 16 hours. Then, it was poured into water and extracted with ethyl acetate. The combined organic layer was dried over sodium sulphate, filtered and concentrated to dryness. The crude product was purified by flash chromatography (2% to 3% MeOH/DCM) to yield 0.93 g (99%) of the title compound as a beige solid.LRMS (m/z): 202 (M+1 )+.

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

Reference:
Patent; ALMIRALL, S.A.; BERNAL ANCHUELA, Francisco Javier; CARRASCAL RIERA, Marta; CATURLA JAVALOYES, Juan Francisco; GRACIA FERRER, Jordi; MATASSA, Victor Giulio; TERRICABRAS BELART, Emma; TALTAVULL MOLL, Joan; ERRA SOLA, Montserrat; WO2012/146666; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 641571-11-1,Some common heterocyclic compound, 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, molecular formula is C11H10F3N3, 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.

Take 250ml three mouth flask,The raw amine 3 (1.00 g, 4.15 mmol) was placed,20 ml of water was added,The temperature of the reaction system was lowered to 0 C,0.23 g of HCl was diluted in 5 ml of water and added dropwise to the reaction system,With the addition of HCl,The viscosity of the reaction system is increasing,So we carry out this step reaction is best to use mechanical stirring,After completion of the dropwise addition, stirring was continued at 0 C for 1 hour,Further, 20 ml of an aqueous solution of 0.28 g of sodium nitrite was added to the reaction system,Stirring was continued for 0.5 h.The above reaction solution system was added to KI (0.83 g) at 0 C,CuI (0.97 g) in 20 ml of water,Plus completed,The whole reaction system was gradually heated to 75 C,The reaction system has a bubble,Nitrogen gas is generated,When bubbles are no longer generated,To the reaction system, 50 ml of ethyl acetate was added to extract the product,The reaction process yield is not high,The reason for this is that the diazonium salts produced by Compound 3 are unstable,With the increase of temperature,Some of the diazonium salts have not decomposed before the iodide ion has been replaced.Too pure silica gel column,Compound 4 was obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, its application will become more common.

Reference:
Patent; Tianjin International Joint Academy of Biomedicine; Rao, Zihe; Yang, Cheng; Chen, Yue; Bai, Cuigai; Sun, Tao; Pan, Chengwen; Meng, Fanfei; Li, Yongtao; Wang, Jinghan; Jiang, Yin; (41 pag.)CN106188005; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 3012-80-4, name is 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde, 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 3012-80-4, category: imidazoles-derivatives

2- hydroxymethyl-l -methyl-1 H-benzimidazole (Compound 49a)A suspension of l -methyl-2-formyl-l H-benzimidazole (500 mg, 3.12 mmol) and NaBH4 (134 mg, 3.43 mmol) in anhydrous THF (25 ml) was stirred for 24 hours at r.t.. The reaction mixture was quenched with water, extracted with EtOAc, dried over Na2S04 and evaporated to dryness in vacuo. The crude was purified by automated flash chromatography (Horizon.(R).TM – Biotage) eluting with CHC13 – 1.7M NH3 sol. in MeOH 100:2 giving the title product as white solid. Yield: 50.4 percent. MS: [ +H]+ = 163.5

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; RECORDATI IRELAND LIMITED; LEONARDI, Amedeo; MOTTA, Gianni; RIVA, Carlo; GUARNERI, Luciano; GRAZIANI, Davide; MARINONI, Fabio; BETTINELLI, Ilaria; WO2011/29633; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 120781-02-4, name is Methyl 2-bromo-1-methyl-1H-imidazole-5-carboxylate, 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 120781-02-4, SDS of cas: 120781-02-4

Methyl 2-(4-(hydroxymethyl)phenyl)-1-methyl-1H-imidazole-5-carboxylate (44). To a solution of methyl2-bromo-1-methyl-1H-imidazole-5-carboxylate5 (515 mg, 2.35 mmol, 1.0 eq) in dioxane (72 mL) was added Pd(PPh3)4 (133 mg, 0.115 mmol, 0.049 eq). The mixture was stirred for 15 min at room temperature before 4-hydroxymethylbenzeneboronic acid (357 mg, 2.35 mmol, 1.0 eq) in 22 mL H2O and K2CO3 (390mg, 2.82 mmol, 1.2 eq) were added. The reaction mixture was heated to 60 C and stirred for 16 h. The solvent was evaporated and the residue was diluted with EtOAc and H2O. The phases were separated and the product was extracted with EtOAc (3x 20 mL). The combined organic extracts were dried overNa2SO4 and the solvent was removed under reduced pressure. The crude product was purified by flash chromatography (10-100% EtOAc linear gradient in hexanes) providing the corresponding benzylicalcohol in 81% (470 mg) 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, Methyl 2-bromo-1-methyl-1H-imidazole-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Fuerst, Rita; Yong Choi, Jun; Knapinska, Anna M.; Smith, Lyndsay; Cameron, Michael D.; Ruiz, Claudia; Fields, Gregg B.; Roush, William R.; Bioorganic and Medicinal Chemistry; vol. 26; 18; (2018); p. 4984 – 4995;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 1003-21-0, name is 5-Bromo-1-methyl-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. COA of Formula: C4H5BrN2

Intermediate 7: Step b (1-Methyl-1H-imidazol-5-yl)(4-nitrophenyl)methanone To a solution of 5-bromo-1-methyl-1H-imidazole (3.22 g, 19.98 mmol) in DCM (15 mL) was added ethyl magnesium bromide (6.66 mL, 19.98 mmol, 3.0 M in diethyl ether) dropwise over a 10 minute period. The resulting orange-red solution was stirred at room temperature for 15 minutes, cooled in an ice bath to 0 C. and N-methoxy-N-methyl-4-nitrobenzamide (3.5 g, 16.65 mmol, Intermediate 7: step a) dissolved in DCM (10 mL) was added dropwise. The ice bath was removed and the solid suspension stirred at room temperature for 48 hours. Water was added followed by 6 M aqueous HCl to a neutral pH (pH=6-7). The aqueous mixture was extracted with DCM, dried over Na2SO4, filtered and concentrated. Et2O was added and the mixture sonicated. The precipitate was collected by filtration and dried to provide the title compound as a tan solid.

The synthetic route of 5-Bromo-1-methyl-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LEONARD, KRISTI A.; BARBAY, KENT; EDWARDS, JAMES P.; KREUTTER, KEVIN D.; KUMMER, DAVID A.; MAHAROOF, UMAR; NISHIMURA, RACHEL; URBANSKI, MAUD; VENKATESAN, HARIHARAN; WANG, AIHUA; WOLIN, RONALD L.; WOODS, CRAIG R.; FOURIE, ANNE; XUE, XIAOHUA; CUMMINGS, MAXWELL D.; US2015/105369; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 72-40-2, 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 72-40-2 as follows.

Example 1 Preparation of Temozolomide (1) 5-Amino-1H-imidazole-4-carboxamide.HCl (4) (25 g, 0.154 mol) (Aldrich 16,496-8), CH2Cl2(0.6 L) and Et3N (45 mL) (Aldrich, 13,206-3) were placed into a dry 2-liter, three-necked flask equipped with dropping funnel, a gas inlet tube, a gas outlet tube, reflux condenser and mechanical stirrer, and maintained under a positive pressure of nitrogen at ambient temperature. The mixture was stirred, and a solution of 400 mL of 4-nitrophenyl chloroformate (34 g, 0.169 mol) (Aldrich, 16,021-0) in CH2Cl2 was added dropwise. The reaction mixture was stirred vigorously for 4 hours and then left to stand for 18 hours at room temperature. The precipitate was collected by vacuum filtration and washed with H2O (1.5 L) to afford the product (3) as a pale yellow solid (42 g, 0.144 mol). 1H NMR (400 MHz, DMSO-d6, delta): 8.40 (d, 2H), 7.83 (s, 1H), 7.74 (d, 2H), 7.08 (bs, 1H), 6.95 (bs, 1H), 6.52 (s, 2H).

According to the analysis of related databases, 72-40-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Schering Corporation; US2002/133006; (2002); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 872-82-2, name is 2-(1H-Imidazol-5-yl)ethanol, molecular formula is C5H8N2O, 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: 2-(1H-Imidazol-5-yl)ethanol

In an ice bath, add slowly to the 4-hydroxyethyl imidazole obtained in Step 1.3 mL of thionyl chloride.After the addition was complete, the mixture was warmed to room temperature and stirred to give a yellow solution.Raise the temperature to 70 C for 1 h.The brown clear solution was removed by rotary evaporation to remove the remaining thionyl chloride to give a brown viscous liquid.Add a small amount of water to dissolve,The pH was adjusted to basic with aqueous sodium carbonate solution and extracted three times with ethyl acetate.The combined organic phases are dried over anhydrous sodium sulfate.Concentrated yellow oily liquid.The crude product is separated by column chromatography.Concentrated 1.3 g of a yellow oily solution was used directly for the next reaction.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 872-82-2, its application will become more common.

Reference:
Patent; Tongwei Co., Ltd.; Zhao Yan; Zhi Yonggang; Zhang Fengping; Cao Jun; Liu Yaomin; Long Yuande; (9 pag.)CN105367500; (2018); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

4856-97-7, name is (1H-Benzoimidazol-2-yl)methanol, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. SDS of cas: 4856-97-7

The method for synthesizing 2-aldehyde benzimidazole in this example is as follows2-Hydroxymethylbenzimidazole (0.1 mol, 14.8 g)The rhodium complex (10-4 mol, 0.0577 g) in Example 1 was added to the reaction vessel.Hydrogen peroxide (30%, 0.3 mol, 9.1 ml) was slowly added to the reaction vessel with stirring.The reaction temperature was controlled at 50C for several hours.The reaction solution was concentrated under reduced pressure,Obtain a solid product,The solid product was dissolved in dichloromethane and subjected to silica gel column chromatography.Get pure product2-aldehyde benzoimidazole 8.32 g,Yield 57%.

The synthetic route of 4856-97-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Lingnan Normal University; Liu Shenggui; Pan Rongkai; Li Guobi; Su Wenyi; (9 pag.)CN107445998; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 57090-88-7, name is 1H-Imidazole-4-carbonitrile, 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 57090-88-7, Formula: C4H3N3

General procedure: A solution of 4-cyano-1H-imidazole (1000 mg, 10.74 mmol), 4-iodo -2-(trifluoromethyl)pyridine (3800 mg,14 mmol), (1R,2R)-N1,N2-dimethyl cyclohexane -1,2-diamine (150 mg, 1.07 mmol), CuI (200 mg, 1.07 mmol) and Cs2CO3 (7000 mg, 21.5 mmol) in 20 mL anhydrous DMF was stirred at 100 oC for 2 hours. The reaction mixture was cooled to room temperature and poured into 200 mL water. The mixture was extracted with ethyl acetate (80 mL*3). The organic layer were combined, washed by brine, dried by Na2SO4 and evaporated. The crude product was purified by silica flash column to afford compound 2 as white solid(1.5 g, 59percent yield).

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:
Article; Zheng, Qiangang; Chen, Ziqi; Wan, Huixin; Tang, Shuai; Ye, Yan; Xu, Yuan; Jiang, Lei; Ding, Jian; Geng, Meiyu; Huang, Min; Huang, Ying; Bioorganic and Medicinal Chemistry Letters; vol. 28; 23-24; (2018); p. 3808 – 3812;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem