Category: imidazoles-derivatives

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. 96797-15-8, name is 4-Iodo-1-trityl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C22H17IN2

To a suspension of 4-iodo-1 -trityl-imidazole (3.00g, 6.88mmol) in THF (55 ml_) at 0C was slowly added isopropylmagnesium chloride (8.6ml_, 17.19mmol), the clear solution was then left to stir for 10 minutes. Trimethyl borate (3.83ml_, 34.38mmol) was added portion wise and the reaction mixture was left to stir for 10 minutes at 0C before being allowed to reach room temperature and stir for a further 10 minutes. 1 M HCI (30 ml_) was then added and the reaction was stirred for 10 minutes. The reaction was quenched by pouring it slowly in to a saturated solution of NaHC03 solution (100 ml_) which was then extracted with EtOAc (3 x 50 ml_). The combined organic phases were then dired over Na2S04 and concentrated in vacuo to give the crude product (1 -tritylimidazol-4-yl)boronic acid (2.53g, 7.15mmol, 103.92% yield) as an off white solid. MS Method 2: RT 1 .47 min, ES+ m/z 355 [M+H]+ H NMR (400MHz, DMSO) delta/ppm: 7.20-7.45 (m, 10H), 6.95-7.10 (m, 7H).

According to the analysis of related databases, 96797-15-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; REDX PHARMA PLC; BHAMRA, Inder; BINGHAM, Matilda; TESTAR, Richard; SARGENT, Louise; DONOGHUE, Craig; (128 pag.)WO2016/55786; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 152628-03-0, The chemical industry reduces the impact on the environment during synthesis 152628-03-0, name is 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid, I believe this compound will play a more active role in future production and life.

7-methyl-2-propyl-3H-benzoimidazole-5-carboxylic acid (10.000 g, 0.045 M) was dissolved in ethanol (50 mL) using a stir bar in a two neck round bottom flask connected to a Liebig condenser. By maintaining the flask at 0-5C thionyl chloride (26.700 g, 0.225 M) was added via dropping funnel. Then the reaction was allowed to reflux for 3-3.5 h. The progress of the reaction was monitored by TLC (using 9.5:0.5 ethyl acetate & methanol mobile phase). After TLC analysis revealed the completion of reaction, excess ethanol and thionyl chloride was stripped under vacuum at 60C. Further reaction mixture was washed with 20 mL of toluene to remove traces of thionyl chloride. Furthermore, 50 mL of toluene was added and reaction mixture was maintained at 0-5 C to get off white precipitate. Then later, the precipitate was stirred for 0.5 h, filtered and washed with toluene (50 mL). Then solid (HCl salt) was dissolved in dichloromethane (60 mL) and pH was adjusted to 7 by addition of 20 % NaHCO3 (12 grams in 60 mL demineralized water). Then dichloromethane layer was washed with 20 mL demineralized water. Dichloromethane was removed under vacuum to get oil which upon cooling afforded the solid. Yield = 8.000 g (71%).

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, 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Mallandur, Bhargava K.; Rangaiah, Gururaja; Harohally, Nanishankar V.; Synthetic Communications; vol. 47; 11; (2017); p. 1065 – 1070;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. Recommanded Product: 1-Methyl-1H-imidazole-2(3H)-thione

Dithiafulvalenyl compound 1 (0.2 mmol), mercapto-thiazole 2 (2 mmol, 10 equiv.), and I2 (0.6 mmol, 3 equiv., 152.4 mg) were dissolved in DMSO (3 mL). The reaction mixture was stirred at 25 C for 12 h under N2 atomsphere. Then quenched with a saturated solution of Na2S2O3 and stirred for half an hour, the solution was extracted with dichloromethane (CH2Cl2). The organic layer was separated, and dried over Na2SO4. Then the organic solvent was removed in vacuo to afford the respective thiadiazole-based dithiafulvalene (DTF) derivatives (3), which were purified by column chromatography (silica gel, PE / CH2Cl2) to afford pure substances.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 60-56-0, its application will become more common.

Reference:
Article; Fu, Huimin; Zhao, Bangtun; Zhu, Weimin; Tetrahedron Letters; vol. 60; 2; (2019); p. 124 – 128;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 288-32-4, 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. 288-32-4 name is 1H-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.

This compound was prepared following a literature procedure.22 To a solution of imidazole 19 (1.11 g, 16 mmol) in NaOH (4 M, 60 mL) wasadded a solution of KI (13.3 g, 80 mmol) and I2 (8.88 g, 35 mmol) inH2O (50 mL) dropwise. The resulting mixture stirred at RT for 10 h.After completion monitored by TLC, the mixture was reduced to pH=8with acetic acid, and the resulting white precipitate was filtered andwashed with cold water. The remaining solid was air dried to afford theproduct 20 as a white creamy solid (4.1 g, 80%). m.p. 188-190 C; Rf(hexane/ethyl acetate 1:1): 0.15; 1H NMR (300 MHz, d6-DMSO): delta 7.77(1H, s); 13C NMR (75 MHz, d6-DMSO): delta 141.8, 86.9. The spectroscopicdata matched that reported in the literature.43

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

Reference:
Article; Zhou, Qingqing; Reekie, Tristan A.; Abbassi, Ramzi H.; Indurthi Venkata, Dinesh; Font, Josep S.; Ryan, Renae M.; Munoz, Lenka; Kassiou, Michael; Bioorganic and Medicinal Chemistry; vol. 26; 22; (2018); p. 5852 – 5869;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 3012-80-4, name is 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde, 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. Product Details of 3012-80-4

1.00 Mmol of n-methyl benzimidazole-2-formaldehyde (a,0.1700g) adding into a reaction kettle of 15 ml of polytetrafluoroethylene, adding 10 ml of methanol to dissolve, and then adding 0.5 mmol of ferrous chloride (0.0811g), wherein 0.25 mmol of 2-aminomethyl pyridine (b and 26 mu l) is added under the condition of stirring), continuously stirring for 3 minutes, sealing, and putting into a baking oven at the temperature of 140 DEG c for heat preservation for 48 hours, and then slowly cooling to obtain a red blocky crystal (about 10 hours to be reduced to the room temperature)), wherein the yield is 71percent (based on b).

The synthetic route of 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangxi Normal University; Zeng Minghua; Zhu Zhonghong; (18 pag.)CN108164566; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 641571-11-1, 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. 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of chloroanhydride in dry CHCl3 was addedamine R2NH2 (one equivalent) and Et3N (1.5 equivalents). The reaction mixture was stirred atroom temperature. The reaction progress was monitored by TLC. Cold water was added to thereaction mixture. The organic layer was separated from the water. The combined organic layers weredried over Na2SO4, filtered, and concentrated under vacuum. The product was purified by columnchromatography on silica gel.

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, 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kalinichenko, Elena; Faryna, Aliaksandr; Kondrateva, Viktoria; Vlasova, Alena; Shevchenko, Valentina; Melnik, Alla; Avdoshko, Olga; Belko, Alla; Molecules; vol. 24; 19; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 52099-72-6, These common heterocyclic compound, 52099-72-6, name is 1-(Prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one, 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.

(3-Isopropenyl-2-oxo-2,3-dihydro-benzoimidazol-1-yl)-acetic acid methyl ester N-isopropenyl-2-benzimidazolone (15.0 g, 86.10 mmol), methyl bromoacetate (13.2 g, 86.1 mmol) and potassium carbonate (14.25 g, 103.26 mmol) were stirred in acetonitrile (300 ml) at room temperature overnight. The next day the reaction mixture was filtered and concentrated to give 21.0 g (99% yield) of (3-isopropenyl-2-oxo-2,3-dihydro-benzoimidazol-1-yl)-acetic acid methyl ester as a clear oil: 1H NMR (DMSO-d6) delta 2.13 (s, 3H), 3.69 (s, 3H), 4.74 (s, 2H), 5.17 (s, 1H), 5.38 (s, 1H), 7.05-7.23 (m, 4H); IR (KBr, cm-1) 2955, 1755, 1714, 1493, 757; MS m/e 247 (MH+).

Statistics shows that 1-(Prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one is playing an increasingly important role. we look forward to future research findings about 52099-72-6.

Reference:
Patent; Yu, Kuo-Long; Wang, Xiangdong; Sun, Yaxiong; Cianci, Christopher; Thuring, Jan Willem; Combrink, Keith; Meanwell, Nicholas; Zhang, Yi; Civiello, Rita L.; US2003/207868; (2003); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 930-62-1, The chemical industry reduces the impact on the environment during synthesis 930-62-1, name is 2,4-Dimethylimidazole, I believe this compound will play a more active role in future production and life.

EXAMPLE 42 1-Acetyl-2,4-dimethylimidazole A solution of 9.6 g (0.10 M) of 2,4-dimethylimidazole in 50 ml of chloroform and 50 ml of toluene was stirred at room temperature and 3.6 ml (0.05 M) of acetyl chloride was added via syringe over 1 minute. The mixture was stirred at room temperature for 2 hours, then the mixture was filtered to remove insoluble solids, and the filtrate concentrated leaving 6.9 g (100%) of 1-acetyl-2,4-dimethylimidazole as a white crystalline solid: nmr (CDCl3) (delta): 7.00 (s, 1H); 2.68 (s, 3H); 2.57 (s, 3H); 2.21 (s, 3H).

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, 2,4-Dimethylimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pfizer Inc.; US4374843; (1983); 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. 37067-95-1, name is 2-Iodo-1-methyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., category: imidazoles-derivatives

A suspension of compound 38 (1.38g; 3.46mmol), 2-iodo-1 -methyl-1 H-imidazole (0.45g; 2.16mmol) and Et3N (3.0mL; 21.6mmol) in DMSO (25ml_) was degassed under N2. Dichlorobis(triphenylphosphine)-palladium (304mg; 0.43mmol) and copper(l) iodide (41 mg; 0.22mmol) were added and the reaction mixture was stirred at 90C for 1 .5 hours. The reaction mixture was cooled to room temperature, poured onto waterand extracted with EtOAc. The organic layer was decanted, washed with brine, dried (MgS04), filtered and evaporated to dryness. The residue was purified bychromatography over silica gel (Irregular SiOH, 15-40mueta”, 300g MERCK; mobile phase, 0.4% NH4OH, 96% DCM, 4% MeOH). The pure fractions were collected and evaporated to dryness. The residue (780mg) was then purified by achiral super critical fluid chromatography on (2 AMINO 6muetaiota 150×21 .2mm; mobile phase, 0.3% 2-propylamine, 80% C02, 20% MeOH). The pure fractions were collected and evaporated to dryness, yielding 430mg (41 %) of compound 300. This fraction was taken up with CH3CN. The precipitate was filtered off and dried yielding 377mg (36%) of compound 300. MP=192C (DSC).

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 37067-95-1.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; SAXTY, Gordon; MURRAY, Christopher William; BERDINI, Valerio; BESONG, Gilbert Ebai; HAMLETT, Christopher Charles Frederick; JOHNSON, Christopher Norbert; WOODHEAD, Steven John; READER, Michael; REES, David Charles; MEVELLEC, Laurence Anne; ANGIBAUD, Patrick Rene; FREYNE, Eddy Jean Edgard; GOVAERTS, Tom Cornelis Hortense; WEERTS, Johan Erwin Edmond; PERERA, Timothy Pietro Suren; GILISSEN, Ronaldus Arnodus Hendrika Joseph; WROBLOWSKI, Berthold; LACRAMPE, Jean Fernand Armand; PAPANIKOS, Alexandra; QUEROLLE, Oliver Alexis Georges; PASQUIER, Elisabeth Therese Jeanne; PILATTE, Isabelle Noelle Constance; BONNET, Pascal Ghislain Andre; EMBRECHTS, Werner Constant Johan; AKKARI, Rhalid; MEERPOEL, Lieven; WO2011/135376; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 33543-78-1, 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. 33543-78-1 name is Ethyl 1H-imidazole-2-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.

a mixture of 3.92 g of ethyl imidazole-2-carboxylate and 3.4 g of 2-bromo-4-cyano-1-indanone is heated at 130¡ã C. for 20 minutes, cooled to 20¡ã C. and dissolved in 20 ml of dichloromethane. The mixture is then concentrated to dryness under reduced pressure (15 mm Hg; 2 kPa) at 40¡ã C. The residue thus obtained is purified by flash chromatography on a silica column, under a nitrogen stream at medium pressure (0.5 bar), with a dichloromethane/methanol (95/5 by volume) mixture as eluent. 1.5 g of ethyl 1-[(4-cyano-1-oxoindan-2-yl)]imidazole-2-carboxylate are thus obtained, which product melts at 159¡ã C. 2-Bromo-4-cyano-1-indanone can be obtained in the following way:

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

Reference:
Patent; Rhone-Poulenc Rorer S.A.; US5902803; (1999); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem