Tag: M.W=200-300

Application of 937013-66-6, The chemical industry reduces the impact on the environment during synthesis 937013-66-6, name is 2-(3-Bromophenyl)-1H-imidazole, I believe this compound will play a more active role in future production and life.

General procedure: A mixture of 4-bromobenzaldehyde (2.78 g; 15.0 mmol), [3-(aminocarbonyl)-phenyl]boronic acid (2.72 g; 16.5 mmol), PdCl2(dppf).CH2Cl2(0.306 g; 0.38 mmol), DME (25 mL) and Na2CO3(25 mL of a 2M solution) was sparged 20 min with N2and heated under reflux for 90 min (consumption of aryl bromide observed by LC/MS). Upon cooling, the mixture was partitioned between EtOAc/H2O, layers were separated, and the aqueous layer was extracted with EtOAc (¡Á2). Combined organics were washed (H2O, brine), dried over Na2SO4and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording the title compound as a tan solid. Used IV-21 and 4- formylphenyl boronic acid Note 1, 2. Note 1 Used 4:1 v/v PhMe/EtOH as organic cosolvents (instead of DME).Note 2 Used Pd(PPh3)4as catalyst (instead of PdCl2(dppf).CH2Cl2).

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-(3-Bromophenyl)-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SMITHKLINE BEECHAM CORP; COWAN, D. J; LARKIN, A. L.; ZHANG, CUNYU; MUSSO, D. L.; GREEN, G. M.; CADILLA, R.; SPEARING, P.K.; BISHOP, M. J.; SPEAKE, J. D.; (219 pag.)CN102516115; (2016); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 6154-30-9, 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. 6154-30-9, name is 2,5-Dibromo-4-nitro-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

4-nitroimidazole (25 g, 221 mmol), sodium bicarbonate (37.1 g, 442 mmol) and water (600 mL) for dilution and then bromine (30 mL, 620 mmol) the temperature at the dropwise addition and the reaction mixture was at 40 C and reacted for 12 hours. After filtering the solids level of the reaction mixture was washed with toluene three times and dried under reduced pressure to give a yield of 2,5-dibromo-4-nitroimidazole of 39.8 g (67%). Prepared 2,5-di-bromo-4-nitroimidazole (39.8 g, 149 mmol) and water (450 mL) and then diluted to sodium iodide (223 g, 1486 mmol) was added and stirring under reflux was 12 sigan. Lower the temperature to room temperature, then filtered washing the solids in the reaction mixture with water, dried under reduced pressure to yield 2-bromo-5-iodo of 37.6 g (80%) was obtained a 4-nitroimidazole. Prepared 2-bromo-5-iodo-4- nitroimidazole (20 g, 63 mmol) in ethanol (190 mL) and then diluted in triethylamine (26.5 mL, 190 mmol) and platinum oxide (108 mg, 0.47 mmol) to give the applied wave after reacting for 3 hours under a hydrogen pressure of 3 bar in the reactor was concentrated under a reduced pressure after filtration with a silica gel and celite. Yield of the reaction mixture with 2-ethyl acetate 10% washed with hydrochloric acid solution to remove the moisture of the obtained organic layer over anhydrous magnesium sulfate, and then the filtrate was concentrated under reduced pressure and isopropyl alcohol and hexane, to obtain 7.9 g (65%) and then diluted with to give a-bromo-4-nitroimidazole.

The synthetic route of 2,5-Dibromo-4-nitro-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Korea Research Institute of Chemical Technology; Kim, Phill Ho; Lee, Sang Ho; Kim, Soo Hyun; Lee, Ir Young; Yoon, Chang Soo; Oh, Tae Kwon; Cho, Sang Rae; (18 pag.)KR101650716; (2016); B1;,
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. 84946-20-3 name is 2-Chloro-1-(4-fluorobenzyl)-1H-benzo[d]imidazole, 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. 84946-20-3

EXAMPLE 20 To a stirred mixture of 3.5 parts of ethyl 4-hydroxy-1-piperidinecarboxylate and 135 parts of N,N-dimethylformamide was added 1 part of a sodium hydride dispersion 50% and stirring was continued for 2 hours at room temperature. After the addition of 5.2 parts of 2-chloro-1-[(4-fluorophenyl)methyl]-1H-benzimidazole, the whole was further stirred overnight at room temperature. The reaction mixture was poured into ice water and the product was extracted with trichloromethane. The extract was dried, filtered and evaporated. The residue was crystallized from 2,2′-oxybispropane, yielding 2.5 parts (31.5%) of ethyl 4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]oxy]-1-piperidinecarboxylate; mp. 94.0 C. (26).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-1-(4-fluorobenzyl)-1H-benzo[d]imidazole, and friends who are interested can also refer to it.

Reference:
Patent; Janssen Pharmaceutica, N.V.; US4695575; (1987); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

28890-99-5, 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. 28890-99-5, name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

250ml four bottles,In the atmosphere of nitrogen gas,0.01 mol of 5H-benzimidazol [1,2-a] benzimidazole was added,0.015 mol of 13- (4-bromophenyl) -10,10-dimethyl-10,13-dihydrobenzofuran [2,3-c] indole [1,2-g] carbazole,0.03 mol of sodium tert-butoxide,1 x 10-4 mol Pd2 (dba) 3,1 x 10-4 mol tri-tert-butylphosphine,150 ml of toluene,Heated to reflux for 24 hours,Sampling point plate, the reaction is complete, natural cooling, filtration, the filtrate steamed, silica gel column, the target product, purity 99.25, yield 49.00%.

The synthetic route of 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Sanyue Photoelectric Technology Co., Ltd.; Wang, Lichun; Li, Chong; Xu, Kai; Zhang, Zhaochao; Ye, Zhonghua; (39 pag.)CN106467552; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A common compound: 120781-02-4, name is Methyl 2-bromo-1-methyl-1H-imidazole-5-carboxylate, belongs to imidazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 120781-02-4

[0277] In a microwave tube was placed N,N-bis(4-methoxybenzyl)-4-((3-phenyl-1H- pyrazol-4-yl)methyl)benzenesulfonamide (138 mg, 0.25 mmol), methyl 2-bromo-i-methyl- 1 H-imidazole-5-carboxylate (54.8 mg, 0.25 mmol), (1 S,2S)-Ni ,N2-dimethylcyclohexane- 1,2- diamine (14.22 mg, 0.100 mmol), Cul (9.52 mg, 0.050 mmol), and Phosphoric acid, potassium salt (159 mg, 0.750 mmol). The air was removed and re-filled with N2 (3 times). Then Toluene (2 ml) was added and the mixture was stirred at 110 C for overnight. After cooling to rt, the mixture was dilute with EtOAc (3 mL) and filtered through celite and eluted with EtOAc. The filtrate was concentrated and the mixture was purified by silica gel chromatography using 10-25% EtOAc/hexane as the eluent to give methyl 2-(4-(4-(N,N- bis(4-methoxybenzyl)sulfamoyl)benzyl)-3 -phenyl- 1 H-pyrazol- 1 -yl)- i-methyl- 1H-imidazole- 5-carboxylate (57 mg, 0.082 mmol, 33.0 % yield). MS (M+H) = 692.

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, 120781-02-4, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE UNITED STATES OF AMERICA AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; VANDERBILT UNIVERSITY; MALONEY, David J.; JADHAV, Ajit; BANTUKALLU, Ganesha Rai; BRIMACOMBE, Kyle Ryan; MOTT, Bryan T.; YANG, Shyh Ming; URBAN, Daniel Jason; HU, Xin; SIMEONOV, Anton; KOUZNETSOVA, Jennifer L.; WATERSON, Alex Gregory; SULIKOWSKI, Gary Allen; KIM, Kwangho; CHRISTOV, Plamen; JANA, Somnath; (387 pag.)WO2016/109559; (2016); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

101184-08-1, Adding a certain compound to certain chemical reactions, such as: 101184-08-1, name is Methyl 4-(1H-imidazol-1-yl)benzoate, 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 101184-08-1.

EXAMPLE 228 1-(Hydroxymethyl)-4-(1H-imidazol-1-yl)benzene To a mixture of 4-(1H-imidazol-1-yl)benzoic acid methyl ester (prepared as described in U.S. Pat. No. 4,804,662) (1.5 g) in THF (25 ml) at -15 C. was added a solution of 1M LAH/THF (10.4) ml). The mixture was stirred for 1/2 hour and allowed to warm to room temperature. The reaction was quenched by addition of water (0.5 ml), and then diluted with methanol (50 ml) and filtered. Concentration of the filtrate yielded 1.2 g (98%) of 1-(hydroxymethyl)-4-(1H-imidazol-1-yl)-benzene.

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 4-(1H-imidazol-1-yl)benzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Merck & Co., Inc.; US5206240; (1993); A;,
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. 5468-66-6 name is 2-(4-Chlorobenzyl)benzimidazole, 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. 5468-66-6

General procedure: To a 25 mL of Schlenk tube equipped with a Teflon septum were added Imidazoles/Pyrazoles (0.4 mmol, 1.0 equiv) and KF (46.4 mg, 2.0 equiv) under Ar, followed by MeCN (3 mL) with stirring. 2 (0.40 mmol, 1.0 equiv) were added subsequently. After stirring for 12 h, the reaction mixture was concentrated. The residue was purified with silica gel chromatography to provide pure product.

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

Reference:
Article; Mao, Ting; Zhao, Liang; Huang, Yang; Lou, Yue-Guang; Yao, Qiuli; Li, Xiao-Fei; He, Chun-Yang; Tetrahedron Letters; vol. 59; 28; (2018); p. 2752 – 2754;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 145022-45-3, name is 1-Ethyl-3-methylimidazolium Methanesulfonate, molecular formula is C7H14N2O3S, 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. 145022-45-3

For the Emim3[PMo12O40] (from this point forward Emim-Mo)synthesis [30], appropriate quantities of prepared H3PMo12O40(0.9 g) and 1-ethyl-3-methylimidazolium methanesulfonate (Alfa Aesar) were dissolved in distilled water (20 mL) separately. When mixed, a precipitate was formed, then filtered and dried at room temperature. Another two hybrids were analogously prepared by using 1-butyl-3-methylimidazolium methanesulfonate (Sigma Aldrich) to produce the Bmim3[PMo12O40] (Bmim-Mo) and 1-hexyl-3-methylimidazolium chloride (Alfa Aesar) for Hexmim3[PMo12O40] (Hexmim-Mo). All the hybrids were used asprepared and their structures are presented in Fig. 1

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 145022-45-3, its application will become more common.

Reference:
Article; Megias-Sayago; Carrasco; Ivanova; Montilla; Galindo; Odriozola; Catalysis Today; vol. 278; (2016); p. 82 – 90;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

3273-68-5, 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 3273-68-5 as follows.

Preparation 4; 5,6-Dihydroimidazor4.5.1-/7c1f1lbenzazepine-2,7(1H,4H)-dione; To a solution of the compound of Preparation 5 (45.0 g, 0.2 mol) in dichloromethane (150 ml) was added thionyl chloride (30 ml, 0.4 mol) and the reaction mixture was stirred at room temperature for 2 h. The mixture was concentrated in vacuo and to the residue was added dichloromethane (1000 ml) and aluminium chloride (84.0 g, 0.6 mol), added portionwise. After stirring at room temperature overnight, the reaction mixture was heated under reflux for 2 h and then concentrated in vacuo. To the residue was added ice water (2000 ml) and concentrated hydrochloric acid (50 ml), followed by additional ice water(2000 ml). The resulting precipitate was collected by filtration, washed with water (4 x 250 ml) and dissolved in sodium hydroxide solution (1 N, 600 ml). The solution was washed with dichloromethane (2 x 150 ml) and cyclohexane (150 ml) and adjusted to pH 10 by addition of dry ice. The solid material was collected by filtration, washed with water (3 x 50 ml) and dried overnight at 40C to give the title compound (30.0 g).1H-NMR (cfe-DMSO): 2.03 – 2.11 (2H), 2.90 – 3.00 (2H), 3.85 – 3.95 (2H), 7.02 – 7.10 (1 H), 7.17 – 7.24 (1 H), 7.50 – 7.58 (1 H)

According to the analysis of related databases, 4-(2-Oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)butanoic acid, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER LIMITED; WO2008/44127; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 1964-77-8, name is 5-Bromo-2-methyl-1H-benzo[d]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. 1964-77-8

To 5-bromo-2-methylbenzimidazole (38 g, 180 mmol) in TEtaF (400 mL) was added di-tert-buty dicarbonate (39 g, 189 mmol). The reaction mixture was stirred at room temperature for 24 h and then concentrated. Ethyl acetate (400 mL) was added to the residue, and the solution was washed with 10% aqueous citric acid (2 x 100 mL), water (100 mL), and brine (100 mL), dried over sodium sulfate, and concentrated. Column chromatography on silica (gradient 20-30% ethyl acetate in hexane) provided 1,1 -dimethyl 6-bromo-2-methyl-lH-benzimidazole-l-carboxylate (27 g, 48% yield) as a beige solid. MS (EI) for Ci3Hi5BrN2O2: 312 (MH+).

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 1964-77-8.

Reference:
Patent; EXELIXIS, INC.; AAY, Naing; ARCALAS, Arlyn; BOWLES, Owen, Joseph; BUSSENIUS, Joerg; CURTIS, Jeffry, Kimo; DEFINA, Steven, Charles; DUBENKO, Larisa; HARRIS, Jason, R.; JACKSON-UGUETO, Eileen, E.; MANALO, Jean-Claire, Limun; KIM, Angie, Inyoung; PACK, Michael; PETO, Csaba, J.; RICE, Kenneth, D.; TSANG, Tsze, H.; WO2010/138487; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem