Month: November 2020

60-56-0, 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. 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Add 1-methyl-2-mercaptoimidazole (0.23 g, 2.04 mmol) to a 150 mL round bottom flask.After stirring potassium carbonate as a base (0.30 g, 2.30 mmol) and acetonitrile as a solvent at 50 C for 40 minutes,After cooling to room temperature, intermediate V (0.43 g, 1.70 mmol) was added and the mixture was warmed to 75 C and the mixture was traced to the end of the reaction.After concentration, extraction, column chromatography separation, drying and the like, the intermediate VIII (0.34 g) is obtained in a yield of 54.2%;White solid,

The synthetic route of 1-Methyl-1H-imidazole-2(3H)-thione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Southwest University; Zhou Chenghe; Man Nabaonei¡¤lamohan¡¤laao¡¤yadafu; Wang Juan; (39 pag.)CN110305064; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 16042-25-4, name is 2-Imidazolecarboxylic acid, 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 16042-25-4, 16042-25-4

PREPARATION 33 1-amino-N-phenyl-1H-imidazole-2-carboxamide a) N-phenyl-1H-imidazole-2-carboxamide To a solution of 1H-imidazole-2-carboxylic acid (0.975 g, 8.7 mmol) in DMF (30 mL) were added aniline (0.67 mL, 8.7 mmol), EDC¡¤HCl (2.54 g, 13.05 mmol) and HOBt (1.76 g, 13.05 mmol). The reaction mixture was stirred at room temperature for 21 hours. Then, it was poured into water and extracted with ethyl acetate. The combined organic layer was dried over sodium sulphate, filtered and concentrated. The crude residue was purified by flash chromatography (2% to 3% methanol in dichloromethane) to yield 1.55 g (96% yield) of the title compound. LRMS (m/z): 188 (M+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, 2-Imidazolecarboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Almirall, S.A.; EP2518070; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 641571-11-1

To a solution of 3 (500 mg, 2.1 mmol) and 48 (489 mg, 2.1 mmol) in CH2CI2 (10mL) was added pyridine (242 mg, 3.1 mmol), dropwise. The reaction was stirred atroom temperature overnight. Water was added and the mixture was extracted with CH2CI2 twice. The combined organic layers were dried over Na2SO4 and concentrated. The residue was purified by silica gel column chromatography to give 49 (180 mg, 20%) as a slightly yellow solid. LCMS (m/z: m+1): 441 .1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 641571-11-1, its application will become more common.

Reference:
Patent; CARDIO THERAPEUTICS PTY LTD; TREUTLEIN, Herbert; ZENG, Jun; DIXON, Ian; JAMES, Ian; PALMER, James T; (169 pag.)WO2018/165718; (2018); 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 1003-21-0 as follows. 1003-21-0

A solution of compound 101a ((1.6 g, 10 mmol), compound sodium 4-(tert-butyl)benzenesulfinate (3.3 g, 15 mmol) and Cul (1.9 g, 10 mmol) in DMF (20 mL) was heated at 110 C for 18 hours under N2. The reaction was then cooled down and filtered. H2O (100 mL) was added to the filtrate and the mixture was extracted with EtOAc (100 mLx 3). The combined organic layers were dried with anhydrous Na2SO4 and concentrated with a Rotavapor. The residue was purified by silica gel chromatography (Petroleum Ether/EtOAc = 10/1 to 2/1) to give the chemical 102a (1.18 g, 42% yield). 1H NMR (CDC13, 400MHz): delta (ppm) 7.83 (d, 2H, J = 8.4 Hz), 7.72 (s, 1H), 7.53 (d, 2H, J = 8.4 Hz), 7.48 (s, 1H), 3.71 (s, 3H), 1.31 (s, 9H). m/z 279 (M+H)+

According to the analysis of related databases, 1003-21-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ST. JUDE CHILDREN’S RESEARCH HOSPITAL; CHEN, Taosheng; LIN, Wenwei; WANG, Yueming; (239 pag.)WO2017/165139; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 23785-21-9 name is Ethyl 1H-imidazole-4-carboxylate, 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. 23785-21-9

The starting material for the above process was obtained as follows: A suspension of ethyl imidazole-4-carboxylate (1.4 g), triethylamine (1.2 g) and chloroform (20 ml) was stirred at room temperature while trityl chloride (3.06 g) was added, and the mixture was stirred at room temperature for 1 h. The resulting solution was washed with water, dried and evaporated to dryness under reduced pressure, and the residue was crystallized from a mixture of ethyl acetate and cyclohexane, to give ethyl 1-tritylimidazole-4-carboxylate, mp 163-164.

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

Reference:
Patent; Imperial Chemical Industries plc; US4935437; (1990); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. 1003-21-0

Example 27: N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-{4-[2- (1-hydroxy-1-methyl-ethyl)-3-methyl-3H-imidazol-4-yl]- [1, 2,3] triazol-1-yl}-4- methyl-benzamide; Ethyl chloroformate (1.19 mL, 12.4 mmol) in MeCN (5 mL) was added dropwise to a 1.00 g (6.21 mmol) of 5-bromo-1-methyl-1H-imidazole (Aldrich) in 30 mL of MeCN under N2. The mixture was stirred and allowed to warm to rt overnight. The mixture was concentrated and the residue was treated with 2M NaOH (100 mL) and extracted with CHUCK (3 x 100 mL). The combined extracts were washed with brine, dried with MgS04, filtered, concentrated, and chromatographed (0-50% EtOAc in hexanes) to give the 5-bromo-1-methyl-lH-imidazole-2-carboxylic acid ethyl ester as a yellow oil (800 mg).

The synthetic route of 1003-21-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM PHARMACEUTICALS, INC.; WO2005/90333; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

4857-06-1, Adding a certain compound to certain chemical reactions, such as: 4857-06-1, name is 2-Chloro-1H-benzo[d]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 4857-06-1.

Step3: Under nitrogen protection,2-Chlorobenzimidazole (1.41 g, 9.2 mmol) was added to the reaction vessel.Phenylboronic acid (1.02 g, 8.4 mmol),Tetrakistriphenylphosphine palladium (0.09g, 0.08mmol),Potassium carbonate (3.48g, 25.2mmol),Toluene 60mL, ethanol 20mL and distilled water 20mL,Stir at 120 C for 3 h.After the end of the reaction, the reaction was quenched with distilled water, ethyl acetate was extracted, and the organic layer was dried over MgSO..The solvent was removed by distillation under reduced pressure.After purification by silica gel column chromatography, Intermediate 75-3 (1.22 g, 75%) was obtained.

According to the analysis of related databases, 4857-06-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Changchun Hai Purunsi Technology Co., Ltd.; Dong Xiuqin; Cai Hui; (34 pag.)CN108409667; (2018); A;,
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. 288-32-4, name is 1H-Imidazole, A new synthetic method of this compound is introduced below., 288-32-4

c: 1-Benzyl-2-chloromethyl-imidazole, oxalate A solution of imidazole (13.6 g, 200 mmol) in 33% aqueous sodium hydroxide is heated to 100 C. for 10 min, the water is removed in vacuo and the crystalline sodium salt is dried at 0.1 mBar and 160 C. for 40 min. The salt is dissolved in 100 ml acetonitrile and is added benzylbromide 23.8 ml, 200 mmol). After stirring at 50 C. for 30 min, the mixture is concentrated in vacuo and the formed NaBr is removed by trituration in ethylacetate and filtration. On concentration in vacuo 1-benzyl-imidazole is obtained as an orange oil.

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; NeuroSearch A/S; US5296493; (1994); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

71759-89-2, 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. 71759-89-2, name is 5-Iodo-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a round-bottom flask was added 4-iodo-1H- imidazole (0.884 g, 4.557 mmol) and cesium carbonate (3.113 g, 9.554 mmol). The flask was capped, dimethylformamide (20 mL) was added, and the atmosphere was vacuum purged thrice with nitrogen. (1-bromoethyl)benzene (884 mg, 4.777 mmol) was added, and the reaction was heated at 80 C for 2 h. The reaction mixture was poured into water and extracted with twicewith ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified by silica gel chromatography (eluting with hexanes and ethyl acetate) to provide 4-iodo-1-(1-phenylethyl)- 111-imidazole (0.954 g, 3.2 mmol, 67%), as a clear yellow oil. LCMS M/Z (M+H) 298.8.

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

Reference:
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; COTE, Alexandre; CRAWFORD, Terry; DUPLESSIS, Martin; GOOD, Andrew, Charles; LEBLANC, Yves; MAGNUSON, Steven, R.; NASVESCHUK, Christopher, G.; ROMERO, F. Anthony; TANG, Yong; TAYLOR, Alexander, M.; (271 pag.)WO2016/138114; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 50995-95-4 name is 2-Propylimidazole, 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. 50995-95-4

EXAMPLE 12 1-(6-Methylergolin-8beta-ylmethyl)-2-propylimidazole 0.68 g of 50% sodium hydride in an oil was added in small portions to a mixture of 2.1 g of 2-propylimidazole and 50 ml of dimethylformamide, and the resulting mixture was stirred for 30 minutes. 2.0 g of 6-methylergolin-8beta-ylmethyl tosylate was added to the mixture which was then heated on a water bath for 2.5 hours. The solvent was distilled off under reduced pressure, and the residue was purified by alumina column chromatography (eluted with ethyl acetate_benzene=1:2, and then with ethyl acetate). The resulting product was recrystallized from acetone-hexane to obtain 0.8 g of the titled compound as colorless needles having a melting point of 223-227 C. (with decomposition). NMR (CDCl3) delta: 1.01 (3H, t, J=6.9 Hz), 1.17 (1H, q, J=12.0 Hz), 1.60-3.12 (11H, m), 2.43 (3H, s), 3.37 (1H, dd, J=14.4, 3.8 Hz), 3.78 (2H, d, J=6.8 Hz), 6.71-7.25 (6H, m), 7.94 (1H, br).

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

Reference:
Patent; Maruko Seiyaku Co., Ltd.; US4713457; (1987); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem