Author: Jessica.F

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. 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, A new synthetic method of this compound is introduced below., SDS of cas: 33543-78-1

General procedure: A mixture of 0.68 g of imidazole, 2.13 g of oxidant(chloramine-B) in presence of 2.5 cm3 (0.01 mol dm-3) of aqueous perchloric acid was stirred at 303 K for 8?10 h. After completion of the reaction (monitored by TLC), the reaction products were neutralized with alkali and extracted with ether. The organic products were subjected to spottests and chromatographic analysis (TLC technique). Further, the reaction mixture was extracted with ethyl acetate and dried over sodium sulfate. The solvent was evaporated under reduced pressure to obtain crude products. The crude products were purified on silica gel column by using petroleum ether and ethyl acetate as solvents to get the pure products. Above analyses revealed the formation of corresponding imidazolones as the oxidation products of imidazoles. 3,5-Dihydroimidazol-4-one, 2-methyl-3,5-dihydroimidazol-4-one, 2-ethyl-3,5-dihydroimidazol-4-one,3,5-dihydro-4-oxoimidazol-2-carbaldehyde, and 3,5-dihydro-4-oxoimidazol-2-ester are the oxidation products of1H-imidazole, 2-methyl-1H-imidazole, 2-ethyl-1H-imidazole,1H-imidazole-2-carbaldehyde, and 1H-imidazole-2-ester, respectively. The mass spectra showed a molecularion peak at m/z = 84 amu (Fig. 1), 99 amu (M 1,Fig. 2), and 112 amu (Fig. 3), clearly confirming 3,5-dihydroimidazol-4-one, 2-methyl-3,5-dihydroimidazol-4-one, and 2-ethyl-3,5-dihydroimidazol-4-one as oxidation products of 1H-imidazole, 2-methyl-1H-imidazole, and2-ethyl-1H-imidazole, respectively. Further these productswere confirmed by NMR data (supplementary material,Figs. 1s?3s). Furthermore, we have succeeded in estimating the products, imidazolones, in case of all the five imidazoles. In some typical experiments, the weight of imidazolones and their percentage yield obtained are recorded in Table 1. The recovery of imidazolones was 87?93 percent yields. Further no reaction was noticed between oxidation products and CAB under prevailing experimental conditions.

The synthetic route of 33543-78-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Manjunatha; Puttaswamy; Monatshefte fur Chemie; vol. 147; 9; (2016); p. 1517 – 1529;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 5400-75-9, These common heterocyclic compound, 5400-75-9, name is 5-Methyl-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.

5-Methyl-1 ,3-diotahydro-2H-benzimiotadazol-2-one (13.1 g, 88.5 mmol) and phosphorus oxychloride(130 rmL, freshly distillated) was charged into three-neck round-bottom flask. The mixture was heated up to boiling point till homogeneous solution was formed. After that the dried hydrogen chloride was bubbled through inlet gas-pipe into the reaction mixture. The mixture was boiled for 15 hours. Excess of phosphorus oxychloride was distillated in vacuo. Mixture of ice and water (250 ml_) was added to residue. The obtained suspension was cooled to room temperature and filtered. Filtrate was alkalinized by aqueous ammonia solution till pH 8, cooled by cold water and filtered crude 2-chloro-6-methyl-1H- benzimidazole. White powder was crystallized from aqueous methanol (water-methanol: 1.1 , 200 mL), washed by aqueous methanol and dried in desiccator under Phosphorous oxide in vacuo. Yield. 8.17 g (55 percent).

Statistics shows that 5-Methyl-1H-benzo[d]imidazol-2(3H)-one is playing an increasingly important role. we look forward to future research findings about 5400-75-9.

Reference:
Patent; CRYSOPTIX K.K.; WO2009/109782; (2009); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

4887-88-1, name is 5-Bromo-1H-benzo[d]imidazole, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Application In Synthesis of 5-Bromo-1H-benzo[d]imidazole

[00512] A. tert-Butyl S-bromo-lH-benzofcphimidazole-l-carboxylate. 5-Bromo- l H-benzo[d] imidazole (0.300 g, 1.52 mmol), di-tert-butyl dicarbonate (0.397 g, 1.82 mmol), triethyl amine (0.307 g, 3.04 mmol) and tetrahydrofuran (10 mL) were stirred at 25 C for 18 h. The solution was condensed under reduced pressure and the product was isolated using Biotage silica gel chromatography (0-80% ethyl acetate in hexanes). Fractions containing product were concentrated to give (0.398 g, 88% yield). MS (ESI) m/z 298 [M+ 1]+.

The synthetic route of 4887-88-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; WO2008/51493; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 21252-69-7, A common heterocyclic compound, 21252-69-7, name is 1-Octyl-1H-imidazole, molecular formula is C11H20N2, 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.

Synthesis of 1-octyl-3(propyl-3-sulfonyl) imidazolium 1 equivalent of 1 -octyl-imidazole was reacted with 1 equivalent of propanesultone at reflux temperature in 10percent toluene as solvent. After 10 hours, the mixture was cooled down at room temperature and then filtrated. The cake was washed with 3 portions of toluene before drying under high vacuum at 60°C.

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; ECOLE D’INGENIEURS ET D’ARCHITECTES DE FRIBOURG; MARTI, Roger; VANOLI, Ennio; AEBY, Sandrine; FISCHER, Fabian; HAPPE, Manuel; WO2013/8172; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 4238-71-5, 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. 4238-71-5, name is 1-Benzyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a cooled (-500C) suspension of 1 -benzyl- lH-imidazole (1,58 g, 10.0 mmol) in anhydrous diethyl ether (50 mL) under nitrogen was added H-butyl lithium (2.5 M in hexanes, 4.0 mL, 10.0 mmol) dropwise. After being stirred for 20 min at – 500C, dry carbon dioxide (passed through Drierite) was bubbled into the reaction mixture for 10 min before it was allowed to warm up to 25C. The heavy precipitate which formed on addition of carbon dioxide to the reaction mixture was filtered to yield a hygroscopic, white solid which was taken up in water (7 mL), acidified to pH = 3, cooled, and induced to crystallize with scratching. Filtration of this precipitate gave a white solid which was suspended in methanol, treated with IiV HCl/diethyl ether (4 mL) and concentrated in vacuo. Lyophilization of the residue from water (5 mL) afforded the HCl salt of Cap- 136 as a white solid (817 mg, 40%). 1H NMR (300 MHz, DMSO-d6) delta 7.94 (d, J= 1.5 Hz, IH), 7.71 (d, J- 1.5 Hz, IH), 7.50-7.31 (m, 5H), 5.77 (s, 2H); Rt = 0.51 min (Cond. MS-W5); 95% homogenity index; LRMS: Anal. CaIc. for [M+H]+ C11H12N2O2: 203.08; found: 203.11.

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, 1-Benzyl-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LOPEZ, Omar D.; CHEN, Qi; BELEMA, Makonen; WO2010/138368; (2010); 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 150058-27-8 as follows. category: imidazoles-derivatives

To the crude CBME (20 g, 1 eq) obtained in the above-mentioned (3) were added methanol:water [(1:1) (160 mL)] and sodium hydroxide (4.4 g, 3 eq) at 25°C – 30°C, and the reaction mixture was stirred at 75°C – 80°C for 4 hr. Using TLC (TLC: 40percent ethyl acetate/hexane, detection method: UV), complete consumption of CBME was confirmed. The reaction mixture was cooled to 25°C – 30°C, and the organic solvent was evaporated under reduced pressure at 40°C – 45°C. To the concentrated residue was added water (200 mL, 10 vol), and the aqueous layer was washed with t-butyl methyl ether (100 mL, 2×5 vol). The aqueous layer was adjusted to pH 5.5 – 6.5 by adding acetic acid (6 mL, 0.3 vol), the obtained slurry was stirred at 25°C-30°C for 1 hr, and the precipitated solid was filtered. The solid was washed with water (40 mL, 2 vol), dried with suction for 15 min, and further dried at 50°C – 55°C for 4 hr to give crude CBCA (16 g). [0327] To the obtained crude CBCA (16 g) were added ethyl acetate (160 mL, 10 vol) and dicyclohexylamine (DCHA) (8.2 g, 1.5 eq), and the mixture was stirred at 25°C – 30°C for 2 hr. The precipitated solid was filtered, washed with ethyl acetate (80 mL, 5 vol), dried with suction for 15 min, and further blast dried at 50°C – 55°C for 4 hr to give a DCHA salt (16 g) of CBCA. To the salt was added isopropyl alcohol (192 mL, 12 vol) at 25°C – 30°C, and the salt was dissolved by heating to 75°C – 85°C, and the mixture was stirred for 15 min. Thereafter, the reaction mixture was cooled to 25°C – 30°C, and stirred at the same temperature for 2 hr. The precipitated solid was filtered, washed with isopropyl alcohol (32 mL, 2 vol), dried with suction for 15 min, and further blast dried at 50°C – 55°C for 4 hr to give a pure DCHA salt (13 g) of CBCA. To this salt was added 25percent aqueous sodium hydroxide solution (120 mL, 10 vol) at 25°C – 30°C, and the mixture was stirred for 15 min, adjusted to pH 5.5 – 6.5 by adding acetic acid (5.8 mL, 0.48 vol), and extracted with methylene chloride (120 mL, 2×5 vol). The extract was combined with the organic layer, and the mixture was washed with water (120 mL, 2×5 vol) and further with saturated brine (60 mL, 5 vol). The organic layer was dried over sodium sulfate, and concentrated under reduced pressure at 40°C – 45°C to give CBCA (9 g, 47percent from BCL).

According to the analysis of related databases, 150058-27-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; API Corporation; SEKI, Masahiko; EP2891650; (2015); 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. 22884-10-2, name is 2-(1H-Imidazol-1-yl)acetic acid, A new synthetic method of this compound is introduced below., Safety of 2-(1H-Imidazol-1-yl)acetic acid

Step (2): Compound 76 + Compound 77 ? Compound 78; To Compound 76 (126 mg, 1.0 mmol) was added dichloromethane (4 ml), Compound 77 (365 mg, 1.00 mmol), and WSCD·HCl (249 mg, 1.30 mmol), followed by stirring at 0C for 1 hour and then at room temperature for 1 hour. Dimethylformamide (2 ml) was added, subsequently stirring for 1 hour, and then concentrated in vacuo to evaporate dichloromethane. Dimethylformamide (2 ml) was added, and then allowed to stand for 3 days. Dichloromethane and water were then added. The organic layer was washed with water, washed with saturated brine, dried over magnesium sulfate, and then filtrated to yield Compound 78 (390 mg, 58% yield, 70% potency).

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; Shionogi&Co., Ltd.; EP2341053; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 1450-93-7, These common heterocyclic compound, 1450-93-7, name is 1H-imidazol-2-amine sulfate(2:1), 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.

EXAMPLE 1 5-(alpha,alpha,alpha-Trifluoro-m-tolyl)imidazo[1,2-a]pyrimidine A mixture of 2.64 g of 2-aminoimidazole hemisulfate, 1.64 g of anhydrous sodium acetate, 4.86 g of 3-dimethylamino-3′-(trifluoromethyl)-acrylophenone and 50 ml of glacial acetic acid was refluxed for six hours. The solvent was removed in vacuo to yield a crude solid. The solid was dissolved in dichloromethane and this solution was washed with saturated aqueous sodium bicarbonate solution. The organic layer was separated and dried over powdered anhydrous sodium sulfate. This solution was passed through a short column of a hydrous magnesium silicate and the effluent was refluxed on a steam bath with the gradual addition of hexane until turbidity was noted. After cooling the desired compound was collected by filtration and gave 1.20 g of pale yellow crystals, m.p. 160-163 C.

Statistics shows that 1H-imidazol-2-amine sulfate(2:1) is playing an increasingly important role. we look forward to future research findings about 1450-93-7.

Reference:
Patent; American Cyanamid Company; US5037980; (1991); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, 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 60-56-0, SDS of cas: 60-56-0

2-mercapto-1-methylimidazole (400 mg, 3.5 mmol) was mixed with K2CO3 (968 mg, 7 mmol) in N, N-dimethylformamide (N, N-dimethylformamide ) (7 mL), followed by addition of di-tert-butyl dicarbonate (1.1 mL, 5.2 mmol). The resulting mixture was then stirred at 60 C for 30 minutes in a nitrogen atmosphere, followed by partitioning with ethyl acetate (40 mL) and water (20 mL). The ethyl acetate layer was then collected and washed with brine (brine), dried over anhydrous MgSO4, and then concentrated under vacuum. Thereafter, the resulting residue was purified by silica gel column chromatography to give a compound (665 mg, yield 89%) as a pale yellow solid.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; HUNGKUANG UNIVERSITY; Chan, JinFeng; Chen, MingRen; LAI, SHITING; GUO, YIQIN; (36 pag.)TW2016/7932; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 24134-09-6, name is 5-Bromo-1,2-dimethyl-1H-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 24134-09-6, Safety of 5-Bromo-1,2-dimethyl-1H-imidazole

A solution of n-BuLi (2.66 M in hexane, 19.5 mL, 51.9 mmol) in THF (100 mL) was stirred under argon at ?-70 C. while a solution of 5-bromo-1,2-dimethyl-1H-imidazole (9.13 g, 52.2 mmol) in THF [60 mL; containing 3 A molecular sieves (18 g)] was added dropwise over 8 minutes via cannula. After stirring for another 4 minutes at ?-70 C., neat ethyl methoxy(methyl)carbamate (2.96 mL, 22.7 mmol) was added dropwise over 3 minutes. This mixture was stirred at ?-70 C. for an additional 5 minutes, and the cold bath was then removed and the slurry was allowed to warm to room temperature with stirring for 1.5 hours. The reaction was then quenched with 5 M aqueous NH4Cl (15 mL), dried (Na2SO4), filtered, and concentrated under high vacuum at 80 C. The resulting orange gummy residue was triturated with hot heptane (?40 mL) and the decanted supernatant was allowed to crystallize to provide impure title compound. This was recrystallized from toluene (?30 mL) to provide, after washing the off-white crystalline filter cake with toluene (2*?3 mL), the title compound as an off-white crystalline solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-1,2-dimethyl-1H-imidazole, and friends who are interested can also refer to it.

Reference:
Patent; Janssen Pharmaceutica NV; Leonard, Kristi A.; Barbay, Kent; Edwards, James P.; Kreutter, Kevin D.; Kummer, David A.; Maharoof, Umar; Nishimura, Rachel; Urbanski, Maud; Venkatesan, Hariharan; Wang, Aihua; Wolin, Ronald L.; Woods, Craig R.; Fourie, Anne; Xue, Xiaohua; Cummings, Maxwell D.; Jones, William Moore; Goldberg, Steven; US2015/105366; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem