Category: imidazoles-derivatives

Synthetic Route of 51605-32-4,Some common heterocyclic compound, 51605-32-4, name is Ethyl 5-methyl-1H-imidazole-4-carboxylate, molecular formula is C7H10N2O2, 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.

and also, starting from 4-methylimidazole-5-carboxylic acid ethyl ester, 1-(2,6-difluorobenzyl)-4-methylimidazole-5-carboxylic acid ethyl ester, m.p. 59°-61° (from hexane) and 1-(2,6-difluorobenzyl)-5-methylimidazole-4-carboxylic acid ethyl ester, m.p. 107°-108° (from toluene/ether), 1-(o-chlorobenzyl)-4-methylimidazole-5-carboxylic acid ethyl ester, m.p. 74°-76°, and 1-(o-chlorobenzyl)-5-methylimidazole-4-carboxylic acid ethyl ester, m.p. 100°-104°; and also, starting from imidazole-4,5-dicarboxylic acid diethyl ester, 1-(2,6-difluorobenzyl)-imidazole-4,5-dicarboxylic acid diethyl ester, m.p. 71°-73° (from petroleum ether), 1-(o-chlorobenzyl)-imidazole-4,5-dicarboxylic acid diethyl ester, m.p. 69°-70° (from ether/hexane) and 1-(o-methylbenzyl)-imidazole-4,5-dicarboxylic acid diethyl ester (oil); and also, starting from 2-methylimidazole-4,5-dicarboxylic acid diethyl ester, 1-(2,6-difluorobenzyl)-2-methylimidazole-4,5-dicarboxylic acid diethyl ester, m.p. 63°-64° (from ether/hexane).

The synthetic route of 51605-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ciba-Geigy Corporation; US4851424; (1989); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 33468-69-8, 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. 33468-69-8, name is 4-(Trifluoromethyl)-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 0.28 g of 2-(3-fluoropyridin-4-yl)-5-(trifluoromethyl)benzoxazole, 0.18 g of 4-(trifluoromethyl)-lH-imidazole, 0.55 g of potassium carbonate and 2 ml of DMF was stirred while heating at 50C for 1.5 hours. Then, the reaction mixture was cooled to room temperature. Water was added to the reaction mixture, followed by extraction with ethyl acetate twice. The combined organic layers were washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.40 g of 2- { 3- [4-(trifluoromethyl)imidazole- 1 -yl]pyridin-4-yl } -5 -(trifluoromethyl)benzoxazole hereinafter, referred to as “active compound 57”).Active compound 57-NMR (CDC13) delta: 9.00 (d, J=5.2 Hz, 1H), 8.84 (s, 1H), 8.31 (d, J=5.1 Hz, 1H), 8.06-8.04 (m, 1H), 7.77-7.75 (m, 1H), 7.74-7.70 (m, 1H), 7.62 (d, J=8.6 Hz, 1H), 7.52-7.50 (m, 1H)

The chemical industry reduces the impact on the environment during synthesis 4-(Trifluoromethyl)-1H-imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; OTSUKI, Junko; WO2011/49221; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 3097-21-0, These common heterocyclic compound, 3097-21-0, name is 1,3-Dimethyl-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.

Take 1,3-dimethyl-1,3-dihydro-2H-benzo [d] imidazol-2-one (1.0 g, 6.1 mmol),Add to chlorosulfonic acid and react at room temperature for 5 hours;After the reaction is completed, water is added to precipitate a solid, which is filtered with suction, recrystallized, and filtered with suction, and the filter cake is dried under infrared.A gray solid was obtained with a yield of 88%.

The synthetic route of 3097-21-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; China Pharmaceutical University; Sun Haopeng; Mo Jun; Li Qihang; Yang Hongyu; Chen Yao; Chen Tingkai; Li Qi; Guo Yan; Liu Zongliang; Feng Feng; Liu Wenyuan; (19 pag.)CN110776494; (2020); 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. 16265-04-6, name is 2-Chloro-1H-imidazole, A new synthetic method of this compound is introduced below., Quality Control of 2-Chloro-1H-imidazole

A reaction vessel A’-1 (1.74g, 17.0mmol), A’-2 (2.07g, 17.0mmol), Tetrakis (triphenylphosphine) palladium (0.7g, 1.08mmol), Potassium carbonate (5.3 g, 38.3mmol), toluene (60 mL), ethanol (20 mL) and distilled water (20 mL) were added, followed by stirring at 60 C for 3 hours.After the reaction was completed, the reaction mixture was cooled to room temperature, extracted with ethyl acetate, dried over MgSO 4, and then the organic solvent was removed, and A-1 (1.67 g, 68%) was obtained by silica column method

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; Choi Don-su; Choi Jin-sol; (70 pag.)KR2019/35043; (2019); 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. 570-22-9, name is 1H-Imidazole-4,5-dicarboxylic acid belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 1H-Imidazole-4,5-dicarboxylic acid

General procedure: 10 mL ethanol solution of 2.0 mmol metal salt was added into 10 mL ethanol solution of 2.0 mmol 4,5-imidazole dicarboxylic acid. Having blended the mixture under reflux for 1 h, methanol solution of 1.0 mmol NaOH was put into hot mixture drop by drop. After 5 h under reflux, solvent of the solution was removed, precipitate was filtered. The precipitates were washed with methanol 3 times and dried in 105 C. Molecular structures of complexes obtained from the reaction of 4,5-imidazole dicarboxylic acid ligand with metal salts were summarized in Fig. 2.1.

The synthetic route of 570-22-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Erdem, Ozlem; Yildiz, Emel; Inorganica Chimica Acta; vol. 438; (2015); p. 1 – 4;,
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. 32673-41-9, name is 4-Imidazolemethanol hydrochloride, A new synthetic method of this compound is introduced below., Recommanded Product: 4-Imidazolemethanol hydrochloride

Referential Example 8 4-(Dichloromethyl)-2-(4-(hydroxymethyl)imidazole-1-yl)-5-nitro-benzotrifluoride To a solution of the compound of Referential example 7 (5.31 g, 18.2 mmol) in tetrahydrofuran (40 ml) were added 4-(hydroxymethyl)imidazole hydrochloride (4.90 g, 36.4 mmol) and triethylamine (7.37 g, 72.8 mmol), and the mixture was refluxed for 1.5 hours. After cooling, ethyl acetate was added to the reaction mixture, washed with brine, then dried over anhydrous magnesium sulfate and solvent was distilled off. The residue obtained was submitted to silica gel column chromatography [ethyl acetate-hexane(3:1)?ethyl acetate] to obtain 5.15 g of title compound as pale yellow powder. Yield 76%. 1H-NMR(DMSO-d6, delta): 4.44(2H,d,J=4.4 Hz), 5.09(1H,t,J=4.4 Hz), 7.39 (1H,s), 7.78(1H,s), 7.92(1H,s), 8.19(1H,s), 8.59(1H,s).

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; Kyorin Pharmaceutical Co., Ltd.; US6562839; (2003); B1;,
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. 2302-25-2, name is 4-Bromo-1H-imidazole, A new synthetic method of this compound is introduced below., Quality Control of 4-Bromo-1H-imidazole

Into a 3 L,4-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen,was placed a solution of sodium hydride (53 g,1.32 mol) in dmf (500 mL),4-bromo-1H-imidazole (172 g,1.17 mol). After stirring for 30 mm at 40 C,a solution of(1-methylcyclopentyl)methyl methanesulfonate (150 g,780 mmol) in dmf (1 L) was addedportionwise. The resulting solution was stined overnight at 90 C. The reaction mixture was cooled to 20C with a water/ice bath and was quenched by the addition of water (3 L). The organic was extracted with ethyl acetate (1 Lx 3) and the combined organic layers were washed with brine (1 L),dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column (1:15 ethyl acetate:petroleum ether) to provide the title compound.

The synthetic route of 2302-25-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO., LTD.; ACTON, John J.; BAO, Jianming; EGBERTSON, Melissa; GAO, Xiaolei; HARRISON, Scott Timothy; KNOWLES, Sandra Lee; LI, Chunsing; LO, Michael Man-Chu; MAZZOLA, Robert D., Jr.; MENG, Zhaoyang; RUDD, Michael T.; SELYUTIN, Oleg; TELLERS, David M.; TONG, Ling; WAI, Jenny Miu-Chun; (125 pag.)WO2017/107089; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 162356-38-9, These common heterocyclic compound, 162356-38-9, name is 2-(2-Bromophenyl)-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.

General procedure: First, 100 mmol 2-phenylimidazole derivative introduced 400 ml of triethylamine. And continuously added with stirring 200 ml alkynyl, 6 mmol triphenylphosphine, 6 mmol of copper iodide (I) and 3 mmol of palladium acetate (II). The reaction mixture was then stirred for 20 hours at 80 . After cooling, the reaction mixture was diluted with 400 ml of methylene chloride, to separate a solid via filtration through a bed of salt C The filtrate was evaporated to dryness. The residue was dissolved in 300 ml of methylene chloride, 100 ml of concentrated aqueous ammonia with individual cleaning solution three times, and then washed three times with 100 ml of water, and dried over magnesium sulfate. After the solvent was removed in vacuo, the crude product was adsorbed onto silica gel (5 grams per gram of crude product silicone), and loaded into a silica gel column. First with dichloromethane to remove byproducts, but will be converted to THF solvent to elute the product. With spherical fractionating tube distillation or sublimation, resulting in the manipulation of the vacuum pump oil / solids release low-boiling components.

The synthetic route of 162356-38-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; STOESSEL, PHILIPP; HEIL, HOLGER; JOOSTEN, DOMINIK; PFLUMM, CHRISTOF; GERHARD, ANJA; BREUNING, ESTHER; (214 pag.)TWI520958; (2016); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 33529-02-1, 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. 33529-02-1, name is 1-Decyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows.

1-Decylimidazole was synthesized according to previous literature. 1-Decylimidazole (5.49 g, 26.3 mmol) and 3-bromopropene (3.1 g, 26.3 mmol) were added to a 100 mL round-bottom flask containing 30 mL ethanol with condenser. The reaction mixture was stirred for 24 h. Solvent was then removed under reduced pressure. The crude product was washed three times with ether and dried in a vacuum oven at 50 C for 24 h to give the 1-allyl-3-decylimidazolium bromide (ADIm). 1-Allyl-3-decylimidazolium bromide: This compound was obtained in 97% as a yellow viscous oil. 1H NMR (DMSO-d6, 400 MHz): delta 9.30 (s, 1H, -N-CH-N-), 7.87 (s, 1H, -N-CH-CH-N-), 7.78 (s, 1H, -N-CH-CH-N-), 6.07 (m, 1H, -CH=CH2), 5.32 (dd, 2H, =CH2), 4.87 (d, 2H, -CH2-CH=CH2), 4.19 (t, 2H, -N-CH2-), 1.79 (m, 2H, -CH2-CH2-), 1.24 (broad, 14H, -CH2-CH3), 0.85 (t, 3H, -CH3).

The chemical industry reduces the impact on the environment during synthesis 1-Decyl-1H-imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zhou, Chuan; Li, Yi-He; Jiang, Zhen-Hua; Ahn, Kwang-Duk; Hu, Tian-Jiao; Wang, Qing-Hua; Wang, Chun-Hua; Chinese Chemical Letters; vol. 27; 5; (2016); p. 685 – 688;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 41806-40-0, name is 1-Methylimidazole-5-carboxylic Acid, molecular formula is C5H6N2O2, 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. Computed Properties of C5H6N2O2

[2514] Take crude (881) from Step A, and dissolve in DMF (60 ml), and add NH(OMe)Me(3.14 g), DEC(6.14 g), HOBT(2.16 g), NMM(11 ml), and stir at room temperature over night. Add 1.0 N HCL until acetic (pH=2), wash with diethyl ether. Add, while stirring, K2CO3 until basic pH=8, saturate with NaCl, and extract with (4×).CH2Cl2. Dry with MgSO4, filter and evaporate to obtain product (882) (3.23 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 41806-40-0, its application will become more common.

Reference:
Patent; Schering Corporation; US2004/122018; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem