Tag: M.W=100-200

Application of 17325-26-7,Some common heterocyclic compound, 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, 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.

d) 3-(2,2-Dimethyl-4-oxo-1 ,2,3,4-tetrahydro-naphthalen-1 -yl)-3H-imidazole-4-carboxylic acid methyl ester; To a solution of 4-hydroxy-3,3-dimethyl-3,4-dihydro-2H-naphthalen-1-one (2.87 g, 13.88 mmol) and methyl 4-imidazolecarboxylate (CASNo. 17325-26-7, 1.25 g, 9.72 mmol) in THF (80 ml.) at 0 0C is added triphenylphosphine (3.68 g, 13.88 mmol) and dimethyl azodicarboxylate (40% in toluene, 5.14 ml_, 13.88 mmol) and the cooling bath is removed. After 15 hours, the mixture is concentrated and the resulting residue is dissolved in ethyl acetate (250 ml.) and is extracted five times with 1 M aqueous HCI (40 mL portions). The acidic aqueous phases are cooled to 0 0C and the pH is adjusted to ca. 12 with 4M aqueous NaOH at 0 0C. The aqueous phase is then extracted three times with dichloromethane. The combined organic layers are dried over MgSO4 and filtered, and concentrated. The resulting residue is purified by silica gel flash chromatography (dichloromethane-methanol, 49:1) to give 3-(2,2-dimethyl-4-oxo-1,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4- carboxylic acid methyl ester; MS: (ESI) m/z 299.0 (M+H)+; 1H NMR (400 MHz, CDCI3) delta ppm 0.97 (S, 3 H), 1.15 (s, 3 H), 2.63 (d, J=16.8 Hz, 1 H), 2.74 (d, J=16.8 Hz, 1 H), 3.93 (s, 3 H), 6.79 (s, 1 H), 7.02 (d, J=7.6 Hz, 1 H), 7.35 (s, 1 H), 7.47 (t, J=7.6 Hz, 1 H), 7.55 (td, J=7.6, 1.5 Hz, 1 H), 7.86 (s, 1 H), 8.13 (dd, J=7.6, 1.5 Hz, 1 H);

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 1H-imidazole-5-carboxylate, its application will become more common.

Reference:
Patent; NOVARTIS AG; WO2008/76336; (2008); A2;,
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. 36947-68-9, name is 2-Isopropyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2-Isopropyl-1H-imidazole

43-a : Synthesis of 1-(4-chloro-2-nitrophenyl)-2-isopropyl-1H-imidazole A mixture of 1.01 g of 4-chloro-1-fluoro-2-nitrobenzene, 634 mg of 2-isopropylimidazole, 1.46 mL of N,N-diisopropylethylamine and 12 mL of acetonitrile was heated under reflux for 15 hours. The solvent was distilled off, water was added, and the reaction liquid was rendered acidic with diluted hydrochloric acid, followed by washing with diethyl ether. The aqueous layer was rendered alkaline with aqueous sodium hydroxide solution, and extracted twice with chloroform. The organic layer was washed with water, dried over magnesium sulfate, and removed of the solvent by distillation to provide 0.98 g of the title compound. 1H-NMR(CDCls,delta):1.22(6H,d,J=6.9Hz),2.5-2.8(1H,m), 6.81(1H,d,J=1.2Hz),7.09(1H,d,J=1.5Hz),7.39(1H,d,J=8.5Hz), 7.71(1H,dd,J=2.3,8.5Hz),8.05(1H,d,J=2.7Hz) MS(m/z):267(M++2), 265(M+)

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 36947-68-9.

Reference:
Patent; ASKA Pharmaceutical Co., Ltd.; EP2123301; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 33468-67-6, name is 2-Methyl-4-(trifluoromethyl)-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 33468-67-6, Quality Control of 2-Methyl-4-(trifluoromethyl)-1H-imidazole

Compound 16.3. 2-Methyl-lH-imidazole-4-carbonitrile. Into a 100-mL round- bottom flask, was placed a solution of 2-methyl-4-(trifluoromethyl)- lH-imidazole (compound 16.2, 300 mg, 2.00 mmol) in 5% ammonium hydroxide (35 mL). The resulting solution was stirred for 4 days at room temperature, then the pH of the solution was adjusted to 7 with acetic acid. The aqueous phase was extracted with of ethyl acetate (3 x 10 mL) and the combined organic layers were dried ( a2S04), filtered, and concentrated under reduced pressur ompound as a light yellow solid.

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-Methyl-4-(trifluoromethyl)-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; 3-V BIOSCIENCES, INC.; HEUER, Timothy Sean; OSLOB, Johan D.; MCDOWELL, Robert S.; JOHNSON, Russell; YANG, Hanbiao; EVANCHIK, Marc; ZAHARIA, Cristiana A.; CAI, Haiying; HU, Lily W.; WO2015/95767; (2015); 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 39070-14-9 as follows. Safety of (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol

General procedure: To a solution of (1-methyl-2-nitro-1H-imidazol-5-yl)methanol (6) (1 eq.) in freshly distilled anhydrous THF (10?mL for 3?mmol of alcohol 6) was added dropwise lithium bis(trimethylsilyl)amide (1?M in THF, 1.1 eq.) at -78?C under an inert atmosphere. The reaction mixture was stirred around 5?min?at -78?C, and a solution of bis(2-chloroethyl)phosphoramidic dichloride (8) (1.1 eq.) in THF (3.3?mmol in 10?mL), previously cooled at -78?C, was added all at once at the same temperature (T0). The reaction mixture was stirred for 15-80?min, before the addition of a solution of the appropriate amine 18-22 (2-2.2 eq.) in THF (3?mL for 5?mmol of amine) and stirring was maintained at -78?C for 5?min to 75?min. These reaction times were determined by 31P NMR monitoring for each compound. The reaction was stopped by addition of water (20?mL for 3?mmol of alcohol 6), concentrated in vacuum and then extracted with EtOAc (3?*?50?mL for 3?mmol of alcohol 6). The combined organic extracts were dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using an eluent gradient (EtOAc/EtOH with TEA or NH4OH) to afford compounds 23-27 as yellow to orange oils.

According to the analysis of related databases, 39070-14-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ghedira, Donia; Voissiere, Aurelien; Peyrode, Caroline; Kraiem, Jamil; Gerard, Yvain; Maubert, Elise; Vivier, Magali; Miot-Noirault, Elisabeth; Chezal, Jean-Michel; Farhat, Farhat; Weber, Valerie; European Journal of Medicinal Chemistry; vol. 158; (2018); p. 51 – 67;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 1122-28-7, 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. 1122-28-7, name is 4,5-Dicyanoimidazole, This compound has unique chemical properties. The synthetic route is as follows.

Example 34 16-(4,5-Bis(5-tetrazolyl)imidazol-1 -yl)hexadecanoic acidA mixture of 16-bromohexadecanoic acid methyl ester (3.50 g, 10.02 mmol), 4,5- dicyanoimidazole (1.52 g, 12.87 mmol), MeCN (30 ml), and K2CO3 (1.95 g, 14.1 mmol) was stirred at 80 0C for 66 h. Water (100 ml) and 1 N HCI (40 ml) were added, and the product was extracted twice with AcOEt. The combined extracts were washed with brine, dried over MgSO4, and concentrated under reduced pressure. Recrystallization from MeOH (10 ml) yielded 3.41 g (88%) of 16-(4,5-dicyanoimidazol-1 -yl)hexadecanoic acid methyl ester as a colorless solid.

The chemical industry reduces the impact on the environment during synthesis 4,5-Dicyanoimidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVO NORDISK A/S; WO2006/5667; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 33543-78-1, These common heterocyclic compound, 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, 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.

Reference example 1 2-hydrazinocarbonylimidazole 2-ethoxycarbonylimidazole was prepared according to the method given in the literature, J. Org. Chem., Vol.43, No.22, 4381 Kenneth L. kirk. 80percent hydrazine hydrate (4.6g, 75mmol) was added dropwise to a solution of 2-ethoxycarbonylimidazole (2.1g, 15mmol) in ethanol (20ml) at room temperature and stirring was continued for 2 h. The precipitate was filtered, washed with water and dried to give the title compound (1.7g, 90.0percent).

Statistics shows that Ethyl 1H-imidazole-2-carboxylate is playing an increasingly important role. we look forward to future research findings about 33543-78-1.

Reference:
Patent; Wakamoto Pharmaceutical Co., Ltd.; EP713876; (1996); 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. 1467-16-9, name is 1H-Imidazole hydrochloride, A new synthetic method of this compound is introduced below., Application In Synthesis of 1H-Imidazole hydrochloride

EXAMPLE 12 N-Cyano-N’-[2-(4-imidazolylmethoxy)ethyl]-N”-methylguanidine A stirred suspension of 4-(2-chloroethoxymethyl(imidazole hydrochloride (14.7 g.) and sodium azide (9.8 g.) in dry dimethylformamide (103 ml.) was maintained at 95 for 5 hours and then set aside overnight at room temperature. Following dilution with water and filtration, the filtrate was concentrated and the residue purified by chromatography on a dry column of alumina using ethanol. The product was basified with potassium carbonate (6.5 g.) in water (3 ml.) and the anhydrous residue was extracted with isopropyl alcohol (3 * 50 ml.). Concentration of the extracts afforded 4-(2-azidoethoxymethyl)imidazole (7.2 g.).

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; Smith Kline & French Laboratories Limited; US3950333; (1976); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 53316-51-1,Some common heterocyclic compound, 53316-51-1, name is 4,5-Dimethyl-1H-imidazole hydrochloride, molecular formula is C5H9ClN2, 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.

A solution of 4,5-dimethyl-1H-imidazole hydrochloride (2.0 g, 15.08 mmol) in DMF (20 mL) was added NaH (60 wt %, 908 mg, 22.63 mmol) in portions at 0 C. under N2. The resulting mixture was stirred for 0.5 h at 0 C. under N2, To the above mixture was added SEM-Cl (3.77 g, 22.63 mmol) dropwise at 0 C. The resulting mixture was stirred for additional 1 h. The reaction was quenched with water (50 mL) at 0 C., then extracted with EtOAc (100 mL¡Á2), washed with brine (50 mL¡Á2), dried and concentrated. The crude residue was purified by reverse phase C18 column chromatography (MeCN/H2O) to give the desired compound (5.12 g, 81.1%) as a yellow oil. ESI-MS m/z 227.10 [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 4,5-Dimethyl-1H-imidazole hydrochloride, its application will become more common.

Reference:
Patent; Enanta Pharmaceuticals, Inc.; Yu, Jianming; Negretti-Emmanuelli, Solymar; Kim, In Jong; Or, Yat Sun; (89 pag.)US2019/315766; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 2466-76-4, 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. 2466-76-4 name is 1-(1H-Imidazol-1-yl)ethanone, 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.

General procedure: To a solution of N -acetylimidazole 7a (1 mmol) and a suitable Baylis-Hillman acetate 1 (1 mmol) in DMF (1 mL), K2CO3 (1 mmol) was added and the resulting mixture was stirred at room temperature until complete consumption of N -acetylimidazole 7a. The reaction mixture was then diluted with water (20 mL) and extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine and dried over anhydrous Na2SO4 . After removal of the solvent under reduced pressure, the residue was puried by flash chromatography over silica gel with EtOAc and hexane (1:1).

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

Reference:
Article; Koeseceli Oezenc, Ay?en; Celik, Ilhami; Koekten, ?ule; Turkish Journal of Chemistry; vol. 41; 3; (2017); p. 323 – 334;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 39021-62-0,Some common heterocyclic compound, 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde, molecular formula is C5H6N2O, 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.

-78 in N2under a 100 mL 3-neck round bottom flask in then-BuLi(hexane of 2.5 M, 0.52 mL, 1.3 mmol) to dry THF (10 mL) of 6-bromo-2,4-dichloro- 3- (2-chlorophenyl) quinolone (387.5 mg, 1 mmol, intermediate 2: step c) was added dropwise to a solution of.30 bungan continuous stirring, and then the, -78 in dry THF (10 mL) of 1-methyl -1H-imidazole-5-carbaldehyde(110 mg, 1 mmol) was added to the solution.The cooling bath was removed and was gradually The mixture was warmed to RT, stirred for 2 hours.The mixture H2next quenched by the addition of O (10 mL), CH2Cl2and extracted with (2 ¡Á 50 mL).The combined organic phases Na2SO4dried and concentrated dry, prep-TLC (CH3OH / CH2Cl2to give evolves to 1:40) to give the title compound as a white solid.

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-5-carbaldehyde, its application will become more common.

Reference:
Patent; Janssen Pharmaceuticals N.V; Leonardo, Christi.A.; Barvei, Kent; Edward, James P.; Gloita, Kevin D.; Kummer, David .A.; Maharoof, Umar; Nishimura, Rachael; Urbanski, Mode; Venkatesan, Hariharan; Wang, Ai Hua; Olin, Ronald L.; Woods, Craig; Fourier, Anne; Shu, Jih; Cumings, Maxwell D.; (86 pag.)KR2016/68948; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem