Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 101184-08-1, name is Methyl 4-(1H-imidazol-1-yl)benzoate, 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 101184-08-1, Quality Control of Methyl 4-(1H-imidazol-1-yl)benzoate

EXAMPLE 228 1-(Hydroxymethyl)-4-(1H-imidazol-1-yl)benzene To a mixture of 4-(1H-imidazol-1-yl)benzoic acid methyl ester (prepared as described in U.S. Pat. No. 4,804,662) (1.5 g) in THF (25 ml) at -15 C. was added a solution of 1M LAH/THF (10.4) ml). The mixture was stirred for 1/2 hour and allowed to warm to room temperature. The reaction was quenched by addition of water (0.5 ml), and then diluted with methanol (50 ml) and filtered. Concentration of the filtrate yielded 1.2 g (98%) of 1-(hydroxymethyl)-4-(1H-imidazol-1-yl)-benzene.

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; Merck & Co., Inc.; US5206240; (1993); A;,
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 13275-42-8 as follows. Recommanded Product: 2-(2-Bromophenyl)-1H-benzo[d]imidazole

General procedure: Equimolar quantity of 2-(2-bromophenyl)-1H-benzo[d] imidazole (2) and aniline derivatives in 45 ml of 1,4-dioxan was refluxed for 14 hr with continuous stirring at 80. The completion of reaction was checked by TLC. The reaction mixture was kept overnight in a refrigerator. The solvent was evaporated and a gummy solid mass was obtained. The gummy solid was then washed with cold water and recrystallized from ethanol and water (4:6) to obtain the compounds (3a-3h).

According to the analysis of related databases, 13275-42-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Singh, Aruna Chandra; Mittal, Nitin; Pathak, Devender; Indian Journal of Heterocyclic Chemistry; vol. 23; 3; (2014); p. 225 – 232;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 28890-99-5, name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]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 28890-99-5, Quality Control of 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole

9-fluorodibenzofuran-2-carbonitrile (1.6 g, 7.58 mmol), 6H-benzimidazolo[1 ,2-a]benzimidazole (1 .65 g, 7.96 mmol), and potassium phosphate (3.38 g, 15.91 mmol) are suspended in 39 mL of NMP, and the mixture is stirred at 185 C for 14 h. After the reaction mixture is cooled at room temperature, it is diluted with 76 mL of water and 38 mL of EtOH. The solid is collected by filtration, and dried in vacuum oven at 50 C. The crude product is purified by column chromatography on silica gel eluting with chloroform to yield 2.21 g (73%) of 9-(benzimidazolo[1 ,2- a]benzimidazol-5-yl)dibenzofuran-2-carbonitrileas a white solid. 1H-NMR (300 MHz, DMSO-afe): delta 8.36-8.26 (m, 2H), 8.08-7.83 (m, 5H), 7.61 -7.54 (m, 2H), 7.48 (td, .7 =1.1 , 7.8 Hz, 4H), 7.36-7.30 (m, 3H), 7.19 (d, J = 7.8 Hz, 1 H)

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; IDEMITSU KOSAN CO., LTD.; RAIMANN, Thomas; SCHAeFER, Thomas; SAITO, Masatoshi; WOLLEB, Heinz; BENEDITO, Flavio Luiz; NISHIMAE, Yuichi; NAKANO, Yuki; NAGASHIMA, Hideaki; (111 pag.)WO2016/157113; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 39513-26-3, 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. 39513-26-3, name is 5-Bromo-1,3-dihydrobenzoimidazol-2-one belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a souUon of (2,3-dmethypheny)boronc add (85 mg, 0.56 mmd) and 5-bromo1 Hbenzo[d] mdazo-2(3H)-.one (100 mg, 0.45 mmd) n 4:1 doxane:water (2.0 mL) were added potassurn phosphate (199 mg, 0.94 mmo) and PdC2(dppf)CH2C2 (19 mg, 0.02 mmofl. The mixture was degassed wfth n[trogen and then heated at 100 C for 16 h. After coong to rt, the reacUon mixture was dUuted wth water and extracted w[th DCM (2X). The combined organic extracts were dried (Na2SO4), fUtered, and concentrated. Purification(FCC, Si02 0 – 50% EtOAc/hexanes) afforded the tifle compound as a white sod (71 mg,63%yied). MS(ES): mass cacd. for C15H14N20, 238.1; m/zfound, 239.1 [M-FH]4. 1HNMR (400 MHz, DMSO-d6) 5 10.64 (s, 2H), 7.20 7.07 (m, 2H), 6.98 (dd, J = 16.2, 7.3Hz, 2H), 6.88 -6.73 (m, 2H), 2.28 (5, 3H), 2.10 (5, 3H).

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, 5-Bromo-1,3-dihydrobenzoimidazol-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; RAVULA, Suchitra; SWANSON, Devin M.; SAVALL, Bradley M.; AMERIKS, Michael K.; (250 pag.)WO2016/176449; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, 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. Quality Control of 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline

4-Methyl-3- { [4-(pyridin-3 -yl)pyrimidin-2-yl] amino } berizoic acid (1 Og), carbonyl diimidazole (6.9 g) and imidazole hydrochloride (5.1 g) was added to N-methylpyrrolidin-2-one (200 mL) in a round bottom flask under nitrogen atmosphere at room temperature and stirred for 60 nuns. The reaction mass was heated to 50-55C and stirred for an hour. 5-trifluoromethyl-3-[4-methyl-H1-imidazolyl] aniline (11.8 g) was added to the reaction mass at 50-55C under nitrogen atmosphere. The reaction mass was further heated to 95-105C ad stirred for 24 hrs. After completion of reaction, thereaction mass was cooled to 25-35C, 5% sodium hydroxide solution was added to it and stirred for 1.5 hrs. The precipitated solid was filtered, washed with water followed by acetone and then dried under vacuum at 50-55C to get the title compound (9.1 g).Purity by HPLC: 99.84%; Amine impurity: 0.04%; Acid impurity: 0.03%

The synthetic route of 641571-11-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LAURUS LABS PRIVATE LIMITED; CHAVA, Satyanarayana; GORANTLA, Seeta Rama Anjaneyulu; INDUKURI, Venkata Sunil Kumar; MOTURU, Venkata Rama Krishna Murthy; JAMJANAM, Srivardhana Rao; SELA, Venkata Purushottama Siva Prasad; WO2015/87343; (2015); A2;,
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. 87233-54-3, name is 2-Chloro-1-(2-ethoxyethyl)-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., name: 2-Chloro-1-(2-ethoxyethyl)-1H-benzo[d]imidazole

c) Intermediate (23) (15.1 g), 2-chloro-1-(2-ethoxyethyl)-1H-benzimidazol (13.5 g) and copper (3.84 g) were stirred at 150 C. for 4 hours. The mixture was taken up in CH2 Cl2 and filtered. The filtrate was washed with a NH4 OH solution and with water. The organic layer was dried, filtered and the solvent evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2 Cl2 /CH3 OH 97/3). The pure fractions were collected and the solvent evaporated, yielding 20 g (77%) of (+-)-ethyl cis-4-[[1-(2-ethoxyethyl)-1H-benzimidazol-2-yl]amino]-2-(phenylmethyl)-1-piperidinecarboxylate (interm. 24).

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; Janssen Pharmaceutica N.V.; US6110939; (2000); 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. 124750-59-0, name is 2-Propyl-1H-imidazole-4,5-dicarboxylic acid dimethyl ester belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 2-Propyl-1H-imidazole-4,5-dicarboxylic acid dimethyl ester

A mixture of dimethyl-2-propylimidazole-4,5-dicarboxylate compound of formula-2a (100 grams), 4-[2-(trityltetrazol-5-yl)phenyl]benzyl bromide compound of formula-3 (296 grams), potassium carbonate (119 grams) in dimethyl formamide (100 ml) and acetone (500 ml) was heated to reflux temperature. The reaction mixture was stirred up to reaction completion and solvent was distilled off completely from the reaction mixture under reduced pressure at below 50C. The reaction mixture was cooled to 25-300C, acetone (150 ml) and water (1000 ml) were added to it then stirred for 60 minutes. The obtained solid was filtered, washed with water and then the wet solid was recrystallized from acetone to provide the title compound.Yield: 285 grams;Purity by HPLC: 98.15%

The synthetic route of 124750-59-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MSN LABORATORIES LIMITED; SATYANARAYANA REDDY, Manne; NAGARAJU, Chakilam; THIRUMALAI RAJAN, Srinivasan; KODANDA RAMPRASAD, Achampeta; RAMA SUBBA REDDY, Karamala; WO2011/21224; (2011); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, molecular formula is C11H10F3N3, 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. Application In Synthesis of 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline

To a solution of 2- (5-ethoxy-6- ( (4-methoxybenzyl) oxy) pyridin-3-yl) -4-ethylpyrimidine-5-carboxylic acid (150 mg 0.366 mmol) 3- (4-methyl-1H-imidazol-1-yl) -5- (trifluoromethyl) aniline (88 mg 0.366 mmol) and Et3N (55.6 mg 0.550 mmol) in 1 4-dioxane (10 mL) stirred under N2at 20 was added DPPA (121 mg 0.440 mmol) in one charge. The reaction mixture was stirred at 80 for 2 h. Then the solution was concentrated. The residue was purified by preparative TLC (DCM/MeOH 101 Rf 0.5) to yield a off white solid of 1- (2- (5-ethoxy-6- ( (4-methoxybenzyl) oxy) pyridin-3-yl) -4-ethylpyrimidin-5-yl) -3- (3- (4-methyl-1H-imidazol-1-yl) -5- (trifluoromethyl) phenyl) urea (50 mg 0.077 mmol 21.07yield) . TLC (DCM/MeOH 101 Rf 0.4) 1HNMR(400 MHz CD3OD) delta9.07 (s 1H) 8.74-8.72 (m 1H) 8.12 (d J 9.3 Hz 2H) 7.98 (br. s. 1H) 7.77-7.75 (m 1H) 7.50 (br. s. 1H) 7.41 (d J 8.6 Hz 2H) 7.35 (s 1H) 6.92 (d J 8.8 Hz 2H) 5.40 (s 2H) 4.17 (d J 7.1 Hz 2H) 3.79 (s 3H) 2.91 (d J 7.5 Hz 2H) 2.26 (s 3H) 1.42 (td J 7.3 14.6 Hz 6H) ES-LCMS m/z 648.3 (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 641571-11-1, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; GLAXOSMITHKLINE (CHINA) R & D COMPANY LIMITED; CHEUNG, Mui; DEMARTINO, Michael P.; EIDAM, Hilary Schenck; GUAN, Huiping Amy; QIN, Donghui; WU, Chengde; GONG, Zhen; YANG, Haiying; YU, Haiyu; ZHANG, Zhiliu; (391 pag.)WO2016/37578; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 39861-21-7, 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 39861-21-7 as follows.

(c) N-[4-(5-Chloro-1H-benzoimidazol-2-yl)phenyl]-2-cyclohexylmethyl-succinamic acid This compound was prepared by the procedure described in Example 1 part (a) from 4-(5-Chloro-1H-benzoimidazol-2-yl) phenylamine and (R)-2-(Cyclohexylmethyl) succinic acid 1-methyl ester to give the crude product (2.0 g, 51%), which was used in the next step without further purification.

According to the analysis of related databases, 39861-21-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Boehringer Ingelheim Pharmaceuticals, Inc.; US6313117; (2001); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 6154-30-9, 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. 6154-30-9, name is 2,5-Dibromo-4-nitro-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A mixture consisting of 2,5-dibromo-4- nitroimidazole (108.3 g, 400 mmol), ethanol (184 ml), sodium iodide (120 g, 800 mmol) was heated to reflux in an argon stream (65-70C, 26 hours). The reaction mixture was cooled to room temperature and the precipitated inorganic salt was removed by filtration. 78% (234 ml) of the filtrate (300 ml) was concentrated and exsiccated under reduced pressure (25-50C). The residue (brown oil, 172 g) was suspended in chilled water (422 ml), and concentrated hydrochloric acid (10 ml) was added thereto such that the pH of the solution became 1 to 2. The thus obtained solution was further stirred under cooling on ice for 2 hours. Thereafter, the precipitated crystals were collected by filtration and then dried at 50C for 24 hours. Yield: 89.2 g (Yield: 89.9 %), pale yellow crystal IR (KBr): 3218, 1537, 1456, 1386, 1336, 1288, 1250, 1156,1048, 969, 829, 756,731, 665 cm~l MS (70 eV) m/z (relative intensity): 319 (80, M+), 317 (82), 154 (100), 106 (78).

The synthetic route of 2,5-Dibromo-4-nitro-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; WO2005/77913; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem