Category: imidazoles-derivatives

Application of 1402838-08-7, 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. 1402838-08-7 name is 2-(1-Trityl-4-imidazolyl)benzaldehyde, 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.

To a three-necked flask was added 2- (1-trityl-1H-imidazole-4-) benzaldehyde (400 mg, 0.97 mmol)Acetylcyclohexane (122 mg, 0.97 mmol)And anhydrous tetrahydrofuran (5 ml)Under nitrogen protection,A solution of sodium ethoxide (85 mg, 1.25 mmol) in ethanol was added at room temperature,Stir at room temperature for 3 h, spin dry solvent,Saturated ammonium chloride (10 ml) was added,The organic layer was extracted with ethyl acetate and dried over anhydrous sodium sulfate. The solvent was dried, acetic acid (1 ml) and ethanol (5 ml) were added, stirred at 90 C for 3 h, cooled to room temperature, and saturated sodium carbonate was added to adjust pH = 10 , Extracted with ethyl acetate, the combined organic layers were dried over anhydrous sodium sulfate,Concentrated solvent,Purification by column chromatography on silica gel afforded compound 9 (210 mg, yield 77%

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(1-Trityl-4-imidazolyl)benzaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; Hinova Pharmaceuticals Inc.; Fan, Lei; Chen, Ke; Li, Xinghai; Chen, Yuanwei; (24 pag.)CN106256830; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1849-02-1, The chemical industry reduces the impact on the environment during synthesis 1849-02-1, name is 2-Chloro-1-methyl-1H-benzo[d]imidazole, I believe this compound will play a more active role in future production and life.

b. 1-methyl-2-(Piperazin-1-yl)-benzimidazole A mixture of 1 g (6.02 mmol) of 2-chloro-1-methyl-benzimidazole and 2.58 g (30 mmol) of piperazine is heated to 150C. without a solvent. The cooled melt is combined successively with water and dilute hydrochloric acid and extracted with dichloromethane. Then the aqueous phase is made alkaline with dilute sodium hydroxide solution and extracted with dichloromethane. The organic phase is dried over sodium sulphate and concentrated by evaporation. The product is purified by column chromatography on silica gel (eluant: dichloromethane/ethanol/ammonia=5:1:0.1). Yield: 0.4 g (30.8% of theory), Melting point: 99 C.

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-Chloro-1-methyl-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Lehmann-Lintz, Thorsten; Heckel, Armin; Thomas, Leo; Mark, Michael; US2003/166637; (2003); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 52099-72-6, name is 1-(Prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one, 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 52099-72-6, HPLC of Formula: C10H10N2O

93.8 ml (150 mmol) of a n-butyllithium solution (about 1.6M in hexane) are added dropwise at 0-5 to 24.8 g (150 mmol) of 2-(N-benzyl-N-methylamino)ethanol dissolved in 250 ml of absolute tetrahydrofuran. After stirring at 0 for 15 minutes 11.7 ml (150 mmol) of methanesulphochloride in 50 ml of tetrahydrofuran are added dropwise at a temperature between 0 and 5 and the reaction mixture is stirred at 0 for 30 minutes. 5.8 g (133 mmol) of a 55% sodium hydride dispersion in mineral oil are washed oil-free with hexane and suspended in 40 ml of dimethylformamide. 23.1 g (132.5 mmol) of 1-(1-methylvinyl)benzimidazolin-2-one in 90 ml of dimethylformamide are subsequently added dropwise at room temperature and the reaction mixture is stirred for a further 15 minutes. This reaction mixture is added dropwise at 0 to the reaction solution described above. Thereafter, the mixture is heated to 70 and stirred for 3 hours. The reaction mixture is subsequently poured into 1 l of ice-water and extracted with 600 ml of methylene chloride. The extract is washed with water, dried over potassium carbonate and evaporated. The thus-obtained product is chromatographed on 500 g of silica gel with methylene chloride and 0-5% isopropanol as the elution agent, whereby there are obtained 26.8 g (63%) of 1-(1-methylvinyl)-3-[2-(N-benzyl-N-methylamino)ethyl]-2-benzimidazolinone as an oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(Prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one, and friends who are interested can also refer to it.

Reference:
Patent; Hoffmann-La Roche Inc.; US4808605; (1989); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 33468-69-8,Some common heterocyclic compound, 33468-69-8, name is 4-(Trifluoromethyl)-1H-imidazole, molecular formula is C4H3F3N2, 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.

4-(Trifluoromethyl)-1 /-/-imidazole (640 mg, 4.7 mmol) was stirred in dry THF (30 ml_) at room temperature under nitrogen. Lithium hexamethyldisilazide (1 M in THF, 4.2 ml_, 4.2 mmol) was added. After 45 minutes, a solution of Intermediate (1-13b) (1.42 g, 4.7 mmol) in dry THF (20 ml_) was added. The reaction was stirred for 12 hours. The reaction was quenched with saturated ammonium chloride and diluted with brine and ethyl acetate. Enough water was added to dissolve the precipitated salts. The aqueous layer was extracted with ethyl acetate, and the combined organics were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with 100% heptane gradient to 80% ethyl acetate/heptane. The appropriate fractions were combined, evaporated, and dried under high vacuum to afford (1-13c) as a yellow oil (689 mg, 2.39 mmol, 57%). m/z 289.2 (M+H)+.

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

Reference:
Patent; PFIZER INC.; BENBOW, John William; LOU, Jihong; PFEFFERKORN, Jeffrey Allen; TU, Meihua Mike; WO2010/29461; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 60-56-0,Some common heterocyclic compound, 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, molecular formula is C4H6N2S, 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 mixing of thiols (1 mmol), sodium hydroxide(1.1 mmol), water (0.5 mL) and methanol (3 mL) were stirred in room temperature. After 30 min,compound 2 (1.1 mmol) in 5 mL CH2Cl2 was added dropwise to the mixture for 36 h-42 h. The mixturewas concentrated in vacuo. The residue was dissolved by CH2Cl2. The solution was extracted threetimes with water. The organic phase was dried overnight with anhydrous sodium sulfate. The solventwas concentrated in vacuo to give crude products. The crude product was purified by silica gelcolumn chromatography.

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-2(3H)-thione, its application will become more common.

Reference:
Article; Yi, Yunpeng; Fu, Yunxing; Dong, Pengcheng; Qin, Wenwen; Liu, Yu; Liang, Jiangping; Shang, Ruofeng; Molecules; vol. 22; 6; (2017);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 496-46-8, 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. 496-46-8, name is Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A mixture of cucurbiturils was prepared by preparing a solution of glycoluril (111 g, 0.781 moles) in water (123 ml, 6.833 moles) under stirring. Sulphuric acid (125 mL, 2.34 moles) and formalin (116 mL, 1.56 moles) were added to the solution of glycoluril and the mixture heated to 100C and held under stirring for 14 hours. The reaction mixture was then cooled to room temperature over a 3 hour time period and the cooled reaction mixture precipitated into methanol (1000 ml). The precipitate was filtered, slurried with methanol (1000 ml), filtered again and dried. (0047) The mixture was determined using nuclear magnetic resonance (1H NMR) imaging to be 20- 25 percent by weight CB[5], 45-55 percent by weight CB[6], 20-25 percent by weight of CB[7], 5-8 percent by weight of CB[8], and less than 1 percent by weight CB[9] and higher cucurbiturils, based on the total weight of cucurbituril in the mixture

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, Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AQDOT LIMITED; COULSTON, Roger; CHEESMAN, Ben; ZHANG, Jing; (20 pag.)WO2018/178647; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 137049-00-4, A common heterocyclic compound, 137049-00-4, name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, molecular formula is C4H5ClN2O2S, 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.

To a solution of tert-butyl (6-(3-((6-amino-,3-dimethyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)oxy)-5-propoxyphenoxy)hexyl)carbamate (67 mg, 0.12 mmol) in DCM (2 ml) were added 1-methyl-1H-imidazole-4-sulfonyl chloride (46 mg, 0.26 mmol) and pyridine (100 muL, 1.24 mmol), the sulfonyl chloride was not fully soluble, so dioxanes (2 mL) was added and the resulting mixture was stirred at 60 C. for 21 h. The resulting suspension was concentrated, then purified by silica-gel chromatography (1:5-1:1 EtOAc/hexanes then 100% EtOAc) and dried to give tert-butyl (6-(3-((1,3-dimethyl-6-(1-methyl-1H-imidazole-4-sulfonamido)-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)oxy)-5-propoxyphenoxy)hexyl)carbamate as a red-colored amorphous solid (58 mg, 68%). MS (ES+) C33H46N6O8S requires: 686. found 687 [M+H]+. 1H NMR (600 MHz, CDCl3) delta: 7.97 (br-s, 1H), 7.60 (s, 1H, overlapped with CHCl3), 7.35 (s, 1H), 7.31 (s, 1H), 7.20 (s, 1H), 6.57 (s, 1H), 6.14 (s, 1H), 5.77 (br-s, 1H), 5.72 (br-s, 1H), 3.86 (t, J=6.4 Hz, 2H), 3.83 (t, J=6.5 Hz, 2H), 3.62 (s, 3H), 3.45 (s, 3H), 3.31 (s, 3H), 3.12 (br-t, J=6.3 Hz, 2H), 1.76 (m, 4H), 1.51 (m, 2H), 1.46 (m, 2H), 1.44 (s, 9H), 1.37 (m, 2H), 1.01 (t, J=7.3 Hz, 3H).

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; Board of Regents, The University of Texas System; Palmer, Wylie; Jones, Philip; Liu, Gang; Petrocchi, Alessia; Reyna, Naphtali; Subrumanian, Govindan; Theroff, Jay; Yau, Anne; (114 pag.)US2016/60260; (2016); 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. 1544-75-8, name is 5-Fluoro-1H-benzo[d]imidazol-2(3H)-one, A new synthetic method of this compound is introduced below., Recommanded Product: 1544-75-8

Obtained through a method the N- acetyl benzylamine piperazine (II) intermediate (19. 6mmol), an alcoholic solution of formaldehyde (16. 3mmol), 5- fluoro-1,3-dihydro-benzimidazol-2-one (16. 3mmol) into 30ml of absolute ethanol, at room temperature for 15h. The reaction was concentrated under reduced pressure to give a crude oil. The crude product was purified by silica gel column chromatography to obtain the free base of N- benzyl-2- {4 – [(5-fluoro-2-oxo-2,3-dihydro-benzo -111- [(1] imidazol-1 yl) methyl] piperazin-1-yl} acetamide (V_19), 4.67g, yield 72.1%.

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; Shanghai Pharmaceutical Industry Research Academy; China State Institute of Pharmaceutical Industry; Li, Jiangqi; Weng, Zhije; Cui, Ning; Jie, Peng; Ma, Xiao; (25 pag.)CN105418506; (2016); 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. 104619-51-4, name is Di(1H-imidazol-1-yl)methanimine, A new synthetic method of this compound is introduced below., COA of Formula: C7H7N5

To a stirred solution of 2-amino-4- (pentafluorosulfanyl) phenol (40) (70 mg, 0.30 mmol) in CH 3CN (1 mL) was added di (1H-imidazol-1-yl) methanimine (96 mg, 0.60 mmol) in one portion at 20 . The reaction mixture was stirred at 80 for 6 h. The solvent was evaporated and the residue was purified by column chromatography (silica gel, petroleum ether/EtOAc 10: 1-2: 1) to afford the titled compound IV (56 mg, 72) as a white solid. [0347] 1H NMR (400MHz, DMSO-d6) delta 7.85 (s, 2 H) , 7.68 (s, 1 H) , 7.52 (s, 1 H) [0348] MS (ESI) : [M+H +] 260.8.

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; XW LABORATORIES INC.; XW LABORATORIES, INC.; XIANG, Jia-Ning; XU, Xuesong; ZHOU, Wei; (123 pag.)WO2018/176343; (2018); 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. 17228-38-5, name is N-Methyl-1H-benzo[d]imidazol-2-amine, A new synthetic method of this compound is introduced below., Product Details of 17228-38-5

To a solution of N-methyl-1H-benzimidazol-2-amine (1.36 g, 9.24 mmol, 1.00) in acetonitrile (40 mL) was added cesium carbonate (12 g, 37.0 mmol, 4 equiv) followed by methyl 4-bromobutanoate (1.40 mL, 2.01 g, 11.1 mmol, 1.0 equiv). The reaction mixture was stirred overnight at RT, then was filtered through Celite and concentrated to dryness in vacuo. The residue was purified by flash column chromatography (silica gel, 100-200 mesh, 0 to 10% methanol in dichloromethane) to afford methyl 4-[2-(methylamino)benzimidazol-1-yl]butanoate (0.65 g, 28%) as an orange oil. LCMS (5 to 95% acetonitrile in water + 0.1% formic acid over 2 mins) retention time 0.88 min, ESI+ found [M+H]

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; GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG; PATEL, Snahel; HAMILTON, Gregory; STIVALA, Craig; CHEN, Huifen; ZHAO, Guiling; (1236 pag.)WO2017/4500; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem