Author: Jessica.F

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. 1964-77-8, name is 5-Bromo-2-methyl-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 1964-77-8

1. To a solution of 5-bromo-2-methyl-lH-benzo[d]imidazole (422 mg, 2.00 mmol) in 20 mL of THF, was added 4.1 mL of t-BuLi solution in hexanes (1.6 M) at -78 C. After 1 hr, a solution of 5-methoxy-l-(phenylsulfonyl)-lH-indole-2-carbaldehyde (693 mg, 2.20 mmol) in 10 mL of THF was added slowly. After 2hr, the reaction mixture was allowed to warm up to RT slowly, quenched with saturated ammonium chloride solution, and extracted with EtOAc. The organic layer was washed with brine, dried (MgS04), and concentrated to give impure (5- methoxy-l-(phenylsulfonyl)-lH-indol-2-yl)(2-methyl-lH-benzo[d]imidazol-5-yl)methanol, which was dissolved in 20 mL of dichloromethane and 20 mL of THF, and reacted with Mn02(3.50 g, 40.0 mmol) overnight at RT. The reaction mixture was diluted with EtOAc, filtered through a pad of Celite, and concentrated to give crude product, which was used for the next step without any further purification.

According to the analysis of related databases, 1964-77-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SRI INTERNATIONAL; JONG, Ling; CHANG, Chih-Tsung; PARK, Jaehyeon; (71 pag.)WO2016/114816; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, 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 39070-14-9, Safety of (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol

To a suspension of N,N’-bis(2-bromoethyl)phosphorodiamidic acid (50mg, 0.16mmol), 1-methyl-2-nitroimidazole-5-methanol (50mg, 0.32mmol), and PPh3 (84mg, 0.32mmol) in THF (15mL) was added DIAD (0.13mL, 0.32mmol) at 0C. After the addition of DIAD, the reaction mixture was warmed to room temperature and stirred overnight. The solvent was removed, and the residue was purified by column chromatography on silica gel (DCM: MeOH=50:1) to afford compound 14 (37mg, 51%) as yellow gum. 1H NMR (400MHz, DMSO) delta 7.25 (s, 1H), 5.05-4.99 (m, 2H), 4.98 (d, J=7.6Hz, 2H), 3.94 (s, 3H), 3.42 (t, J=6.9Hz, 4H), 3.17-3.05 (m, 4H). 13C NMR (101MHz, DMSO) delta 146.1, 134.1(d, J=8.0Hz), 128.2, 55.7 (d, J=4.3Hz), 42.7, 34.3, 34.1 (d, J=5.0Hz). HRMS (ESI): m/z Calcd for C9H17Br2N5O4P, [M+H]+: 469.9204, found: 469.9186.

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-Methyl-2-nitro-1H-imidazol-5-yl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Jin, Chen; Zhang, Qiumeng; Lu, Wei; European Journal of Medicinal Chemistry; vol. 132; (2017); p. 135 – 141;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 57531-37-0, 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. 57531-37-0, name is 2-Chloro-5-nitroimidazole, This compound has unique chemical properties. The synthetic route is as follows.

Example 1 Preparation of 2-chloro-1-(3-chloro-2-hydroxypropyl)-4-nitroimidazole Sodium hydrogencarbonate (1.25 g, 14.91 mmol) 5 was added to a solution of 2-chloro-4-nitro-1H-imidazole (2 g, 13.56 mmol) and epichlorohydrin (1.38 g, 14.91 mmol) in acetonitrile (60 ml), and the resulting mixture was stirred under reflux for 4 hours. The reaction mixture was allowed to return to room 10 temperature, and concentrated under reduced pressure. To the residue, water (20 ml) was added, the resulting mixture was extracted with methylene chloride (15 ml) twice, and the extracts were dried over sodium sulfate, and then filtrated. The filtrate was concentrated 15 under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/n-hexane = 1/1) to afford 2-chloro-1-(3-chloro-2-hydroxypropyl)-4-nitroimidazole (2.04 g, yield 63percent) as a light yellow oil. 20 1H-NMR (CDCl3) deltappm: 3.51 – 3.70 (2H, m), 4.02 – 4.35 (4H, m), 7.92 (1H, s).

The chemical industry reduces the impact on the environment during synthesis 2-Chloro-5-nitroimidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; EP1555267; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 1072-62-4,Some common heterocyclic compound, 1072-62-4, name is 2-Ethyl-1H-imidazole, molecular formula is C5H8N2, 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: (bromomethyl)-5-fluorophenyl)(2-fluoro-4,5-dimethoxyphenyl)methanone 4 (0.25 g, 0.68 mmol, 1.0 equiv) and 4-hydroxyl piperidine (150 muL, 1.35 mmol, 2.0 equiv) weredissolved in anhydrous dichloromethane (10 mL) and dryK2CO3 (100 mg, 0.72 mmol, 1.1 equiv) was added, and thenthe mixture was stirred at room temperature for 12 h. Thesolvent was removed by rotary evaporation and the residuewas purified by flash column chromatography over silica gelwith the system (14% ethyl acetate/petroleum ether, adding1.4% ammonia water) to obtain compound (5-fluoro-2-((4-hydroxypiperidin-1-yl)methyl)phenyl) 2-fluoro-4,5-dimethoxyphenyl)methanone 5a (0.2 g, 77%) as a yellow solid.The intermediates 5b-5g, 7a-7k, 9a-9g, 11a-11b wereprepared in a similar manner

The synthetic route of 1072-62-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Feng, Xiu E; Kong, De Peng; Ban, Shu Rong; Ge, Rui; Li, Qing Shan; Medicinal Chemistry Research; vol. 28; 8; (2019); p. 1319 – 1337;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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