Month: September 2021

17289-25-7, name is (1-Methyl-1H-imidazol-4-yl)methanol, 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. Recommanded Product: (1-Methyl-1H-imidazol-4-yl)methanol

190b) 1 -Methyl-1 H-imidazole-4-carbal A solution of (1 -methyl-1 H-imidazol-4-yl)methanol (5 g, 44.6 mmol) in acetone (50 mL) was added manganese(IV) oxide (19.38 g, 223 mmol) slowly under nitrogen at room temperature. The reaction mixture was stirred at 60 C for 12 h. The solid was filtered and the liquid was concentrated to obtain the title compound 1 -methyl-1 H-imidazole-4- carbaldehyde (4.12 g, 34.4 mmol, 77 % yield) which was used in next step without further purification. LC-MS m/z 1 1 1 .2 (M+H)+, 0.49 min (ret. time).

The synthetic route of 17289-25-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ASTEX THERAPEUTICS LIMITED; CALLAHAN, James Francis; KERNS, Jeffrey K.; LI, Peng; LI, Tindy; MCCLELAND, Brent W.; NIE, Hong; PERO, Joseph E.; DAVIES, Thomas Glanmor; GRAZIA CARR, Maria; GRIFFITHS-JONES, Charlotte Mary; HEIGHTMAN, Thomas Daniel; NORTON, David; VERDONK, Marinus Leendert; WOOLFORD, Alison Jo-Anne; WILLEMS, Hendrika Maria Gerarda; (664 pag.)WO2017/60854; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 60-56-0,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.

To a solution of 7-[4-(2-butoxyethoxy)phenyl]-N-[4-(hydroxymethyl)phenyl]-1-isobutyl-2,3-dihydro-1-benzazepine-4-carboxamide (500 mg) in THF (10 ml) was added 1 droplet of pyridine, and thionyl chloride (0.09 ml) was added to the mixture at 0C. The mixture was allowed to be at room temperature under nitrogen atmosphere, and stirred for 1 hour. The solvent and excess thionyl chloride were distilled off under reduced pressure, and the residue was dissolved in THF (10 ml). This solution was added to a solution of 2-mercapto-1-methylimidazole (137 mg) and triethylamine (1.67 ml) in THF (10 ml) at 0C, and the mixture was heated overnight under nitrogen atmosphere at 50C. The mixture was allowed to be cooled, water was added to the mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure. The obtained residue was separated and purified by silica gel column chromatography (hexane:ethyl acetate = 1:2), to give 7-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-N-[4-[[(1-methylimidazol-2-yl)sulfanyl]methyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide (437 mg) (Compound 358) as yellow amorphous. 1H-NMR (200 MHz, CDCl3) delta 0.90 to 0.99 (9H, m), 1.30 to 1.45 (2H, m), 1.50 to 1.70 (2H, m), 1.95 to 2.20 (1H, m), 2.90 to 2.97 (2H, m), 3.19 (2H, d, J = 7.4 Hz), 3.28 (3H, s), 3.30 to 3.40 (2H, m), 3.55 (2H, t, J = 6.6 Hz), 3.80 (2H, t, J = 4.6 Hz), 4.13 to 4.18 (4H, m), 6.87 to 7.11 (7H, m), 7.37 to 7.56 (8H, m). Elemental Analysis for C38H46N4O3S·0.3H2O Calcd. C, 70.84; H, 7.29; N, 8.70; Found. C, 70.62; H, 7.49; N, 8.91.

The synthetic route of 60-56-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1422228; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 1219741-21-5, name is 5-Chloro-6-iodo-1H-benzo[d]imidazole-2(3H)-thione, 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. COA of Formula: C7H4ClIN2S

Next, a solution of 5-chloro-6-iodo-2,3-dihydro-1H-1,3-benzodiazole-2-thione (600 mg, 1.93 mmol, 1.00 equiv) in N,N-dimethylformamide (50 mL) and potassium hydroxide (325 mg, 5.80 mmol, 3.00 equiv) was placed into a 100-mL sealed tube. CF3I(g) was then introduced. The resulting solution was stirred overnight at 80 C. The resulting solution was diluted with 250 mL of H2O. The resulting solution was extracted with 3×300 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 100 mL of brine. The mixture was dried over sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1/1). This resulted in 240 mg (33%) of 5-chloro-6-iodo-2-[(trifluoromethyl)sulfanyl]-1H-1,3-benzodiazole as a yellow solid.

The synthetic route of 5-Chloro-6-iodo-1H-benzo[d]imidazole-2(3H)-thione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERIAL LIMITED; Meng, Charles Q.; US2013/281392; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

3543-72-4, name is Ethyl 4-(1-methyl-5-nitro-1H-benzo[d]imidazol-2-yl)butanoate, 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. Safety of Ethyl 4-(1-methyl-5-nitro-1H-benzo[d]imidazol-2-yl)butanoate

In the hydrogenation reaction kettle by adding 50 g 1 – methyl -5 – nitro – 1H – benzimidazole -2 – butyric acid ethyl ester (compound of formula II), 2.5 g 5% palladium/carbon, 1.3 L methanol, 475 ml ethyl acetate, hydrogen pressure control in the 0.1 – 0.2 mpa, reaction solution is 25 C reaction 15 hours, TLC monitoring end point of the reaction to the reaction is complete.Responds the fluid in 35 C decompression filter, collecting the filtrate, the filtrate concentrated under reduced pressure to dry after, adding 75 ml ethyl acetate, 70 C stirring 0.5 hours, cooling to 5 C stirring 0.5 hours, for 5 C standing crystallization 2 hours, filtering, washing the filter cake with acetic acid ethyl ester, filtration cake 50 C decompression drying 5 hours, formula I compound 35 g, yield 77.8%.

The synthetic route of 3543-72-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhengda Tianqing Pharmaceutical Group Co., Ltd.; Wang Hua; Zhang Aiming; Xia Chunguang; Zhang Xiquan; Yi Yan; (6 pag.)CN109694353; (2019); 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. 3752-24-7, name is 4,5,6,7-Tetrahydro-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., Application In Synthesis of 4,5,6,7-Tetrahydro-1H-benzo[d]imidazole

EXAMPLE 7 1-[1-(3,4-Dichloro-phenyl)-1H-imidazol-4-yl-methyl]-4,5,6,7-tetrahydro-1H-benzoimidazole-, Hydrochloride (1:2) Reaction of 4,5,6,7-tetrahydrobenzimidazole with sodium hydride followed by treatment with 4-chloromethyl-1-(3,4-dichloro-phenyl)-1H-imidazole led after extractive workup and chromatography to the free base of the title compound which was converted into its white hydrochloride salt. Mp.>250 C. (MeOH/Et2O), MS: m/e=346 (M+).

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; Alanine, Alexander; Buettelmann, Bernd; Heitz Neidhart, Marie-Paule; Jaeschke, Georg; Pinard, Emmanuel; Wyler, Rene; US2002/151715; (2002); 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. 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, A new synthetic method of this compound is introduced below., HPLC of Formula: C5H6N2O2

c) 3-{[(2-Bromo-benzyl)-methyl-carbamoyl]-methyl}-3H-imidazole-4-carboxylic acid methyl ester; To a solution of N-(2-bromo-benzyl)-2-hydroxy-N-methyl-acetamide (1.02 g, 3.95 mmol) in THF (40 mL) at 0 0C is added triphenylphosphine (1.15 g, 4.36 mmol), methyl 4- imidazolecarboxylate (CASNo. 17325-26-7, 0.50 g, 3.96 mmol) and diisopropyl azodicarboxylate ( 0.85 mL, 4.36 mmol). The reaction is permitted to warm to room temperature and allowed to stir 18 hours. The reaction is then adsorbed directly onto silica gel and submitted to silica gel flash chromatography (diethylamine-methanol- dichloromethane, 1 :3:96) to provide 3-{[(2-bomo-benzyl)-methyl-carbamoyl]-methyl}-3H- imidazole-4-carboxylic acid methyl ester; MS: (ESI) m/z 366.2, 368.2 (M+H)+.

The synthetic route of 17325-26-7 has been constantly updated, and we look forward to future research findings.

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. 10040-98-9, name is 4-Imidazol-1-yl-benzaldehyde, This compound has unique chemical properties. The synthetic route is as follows., Formula: C10H8N2O

General procedure: The 4-alkyl(aryl)aminobenzaldehyde (1 mmol) was added to(RMe2Si)3CLi, R=H,Me (1 mmol) in THF under argon. The mixturewas reacted according to Tables 1 and 2. The reaction was quenchedwith H2O, extracted with CH2Cl2 and dried over Na2SO4. The solventwas evaporated under reduced pressure and the residue was purifiedby preparative column chromatography (n-hexane/ethylacetate) andthe corresponding products were obtained.

According to the analysis of related databases, 10040-98-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Safa, Kazem Dindar; Nadimi, Sanaz; Alyari, Maryam; Journal of Chemical Research; vol. 38; 8; (2014); p. 498 – 501;,
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. 89830-98-8, name is 5-Cyclopropyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 5-Cyclopropyl-1H-imidazole

Into a 50-mL round-bottom flask purged with nitrogen, was placed a solution of 2,4- dichloro-5-(trifluoromethyl)pyridine (800 mg, 3.7 mmol) in DMF (2 mL), 4-cyclopropyl-1H- imidazole (482 mg, 4.4 mmol) and K2C03 (1.53 g, 11.1 mmol). The resulting mixture was stirred at 70°C overnight. Solvent was removed in vacuo. Purification of the crude product on a silica gel column with 30percent EtOAc/PE afforded 360 mg (38percent) of 2-chloro-4-(4-cyclopropyl- 1 H-imidazol- 1 -yl)-5 -(trifluoromethyl)pyridine as a yellow solid.

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 89830-98-8.

Reference:
Patent; ENANTA PHARMACEUTICALS, INC.; WANG, Guoqiang; SHEN, Ruichao; LONG, Jiang; MA, Jun; XING, Xuechao; HE, Yong; GRANGER, Brett; HE, Jing; WANG, Bin; OR, Yat, Sun; (125 pag.)WO2018/209354; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 33543-78-1,Some common heterocyclic compound, 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, molecular formula is C6H8N2O2, 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.

The ethyl 1-(4-cyanomethyl-1-oxoindan-2yl)imidazole-2-carboxylate can be obtained in the following manner: a solution of 1.8 g of ethyl imidazole-2-carboxylate in 30 ml of acetone is supplemented with 8.6 g of potassium carbonate. This suspension is heated at reflux for 15 minutes and then a solution of 3.22 g of 2-bromo-4-(cyanomethyl)indan-1-one in 30 ml of acetone is added. After stirring for 4 hours at reflux temperature, the reaction medium is brought to a temperature close to 20° C. and filtered on sintered glass. The filtrate is evaporated and 2.7 g of a black solid are obtained. The purification by flash chromatography on a silica column (eluent: dichloromethane-ethyl acetate (50-50 by volume)) of this solid gives 0.62 g of ethyl 1-(4-cyanomethyl-1-oxoindan-2-yl)imidazole-2-carboxylate in the form of a brown solid [mass spectrum m/z 309 (M+), 236 ((M-CO2 Et), +), 141 ((C6 H9 N2)+), 68((C3 H4)+)].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 1H-imidazole-2-carboxylate, its application will become more common.

Reference:
Patent; Rhone Poulenc Rorer S.A.; US5990108; (1999); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 288-32-4, name is 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 288-32-4, COA of Formula: C3H4N2

General procedure: A THF solution of imidazole (1 equivalent) is added to a suspension of NaH (1.1 equivalents) (60 % in paraffin oil) previously stirred in n-hexane for 15 min. The imidazole solution is added dropwise over a period of 25-30 min at 5-10 C to avoid vigorous liberation of H2 gas. Once H2 gas evolution ceased, the suspension of imidazole sodium is stirred at RT for 2-3 h to favor complete formation of NaIm salt. To this suspension, corresponding R-Br (0.90 equivalents), was added dropwise over a period of 30 min and further stirred for 3 h or longer to achieve uniform mixing indicated by vertex formation. The thoroughly stirred reaction mixture then was refluxed overnight at 60-65 C. The reaction mass was then allowed to cool and filtered to remove NaBr salt. THF is removed under a rotary evaporator and DCM is added to the resultant brownish liquid followed by the addition of activated charcoal and anhydrous Na2SO4, stirred for 2-3 h and filtered over Celite. A Celite bed was washed with DCM and DCM removed under vacuum leading to a pale yellowish liquid. The NMR spectra checked in CDCl3 and matches with literature reports [20].

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:
Article; Aher, Sainath Babaji; Bhagat, Pundlik Rambhau; Research on Chemical Intermediates; vol. 42; 6; (2016); p. 5587 – 5596;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem