Tag: M.W=200-300

Application of 641571-11-1, 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. 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of chloroanhydride in dry CHCl3 was addedamine R2NH2 (one equivalent) and Et3N (1.5 equivalents). The reaction mixture was stirred atroom temperature. The reaction progress was monitored by TLC. Cold water was added to thereaction mixture. The organic layer was separated from the water. The combined organic layers weredried over Na2SO4, filtered, and concentrated under vacuum. The product was purified by columnchromatography on silica gel.

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, 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kalinichenko, Elena; Faryna, Aliaksandr; Kondrateva, Viktoria; Vlasova, Alena; Shevchenko, Valentina; Melnik, Alla; Avdoshko, Olga; Belko, Alla; Molecules; vol. 24; 19; (2019);,
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. 37067-95-1, name is 2-Iodo-1-methyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., category: imidazoles-derivatives

A suspension of compound 38 (1.38g; 3.46mmol), 2-iodo-1 -methyl-1 H-imidazole (0.45g; 2.16mmol) and Et3N (3.0mL; 21.6mmol) in DMSO (25ml_) was degassed under N2. Dichlorobis(triphenylphosphine)-palladium (304mg; 0.43mmol) and copper(l) iodide (41 mg; 0.22mmol) were added and the reaction mixture was stirred at 90C for 1 .5 hours. The reaction mixture was cooled to room temperature, poured onto waterand extracted with EtOAc. The organic layer was decanted, washed with brine, dried (MgS04), filtered and evaporated to dryness. The residue was purified bychromatography over silica gel (Irregular SiOH, 15-40mueta”, 300g MERCK; mobile phase, 0.4% NH4OH, 96% DCM, 4% MeOH). The pure fractions were collected and evaporated to dryness. The residue (780mg) was then purified by achiral super critical fluid chromatography on (2 AMINO 6muetaiota 150×21 .2mm; mobile phase, 0.3% 2-propylamine, 80% C02, 20% MeOH). The pure fractions were collected and evaporated to dryness, yielding 430mg (41 %) of compound 300. This fraction was taken up with CH3CN. The precipitate was filtered off and dried yielding 377mg (36%) of compound 300. MP=192C (DSC).

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 37067-95-1.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; SAXTY, Gordon; MURRAY, Christopher William; BERDINI, Valerio; BESONG, Gilbert Ebai; HAMLETT, Christopher Charles Frederick; JOHNSON, Christopher Norbert; WOODHEAD, Steven John; READER, Michael; REES, David Charles; MEVELLEC, Laurence Anne; ANGIBAUD, Patrick Rene; FREYNE, Eddy Jean Edgard; GOVAERTS, Tom Cornelis Hortense; WEERTS, Johan Erwin Edmond; PERERA, Timothy Pietro Suren; GILISSEN, Ronaldus Arnodus Hendrika Joseph; WROBLOWSKI, Berthold; LACRAMPE, Jean Fernand Armand; PAPANIKOS, Alexandra; QUEROLLE, Oliver Alexis Georges; PASQUIER, Elisabeth Therese Jeanne; PILATTE, Isabelle Noelle Constance; BONNET, Pascal Ghislain Andre; EMBRECHTS, Werner Constant Johan; AKKARI, Rhalid; MEERPOEL, Lieven; WO2011/135376; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 152628-03-0, 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. 152628-03-0, name is 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 15; PREPARATION OF 2-n-PROPYL-4-METHYL-6-(1-BENZIMIDAZOLE-2-YL) BENZIMIDAZOLE (FORMULA XI); 5 g of 2-n-propyl-4-methyl-benzimiclazoltheta-6-carboxylic acid of Formula III, obtained in Example 1 , and 2.6 g of o-phenylenediamine, were charged into a round bottom flask containing 15 g of polyphosphoric acid (PPA). Reaction mass was heated to 150-155 C and maintained for 4-5 hours. Cooled the reaction mass to 70-80 C and charged 50 ml of water. Stirred for 45-60 minutes at the same temperature and then cooled to 10-15 C. Reaction mass pH was adjusted to 5-6 with 10% aqueous sodium hydroxide solution (200 ml) and stirred for 15-30 minutes. Filtered the solid and washed with 10 ml of water.The wet solid was charged into a flask and 50 ml of water was added. The contents were heated to 70-80 C and stirred for 30-45 minutes. Cooled to 25-35 C and stirred for 30-45 minutes. Filtered the solid and washed with 10 ml of water. Dried the solid at 50-55 C for 4-5 hours to afford 7.2 g of the title compound.

The chemical industry reduces the impact on the environment during synthesis 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; DR. REDDY’S LABORATORIES LTD.; DR. REDDY’S LABORATORIES, INC.; WO2006/44754; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

33529-02-1, name is 1-Decyl-1H-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. category: imidazoles-derivatives

4-Vinylbenzyl chloride (1.00 g, 6.55 mmol) and 1-decylimidazole (1.50 g, 7.20 mmol) were stirred in acetonitrile (40 mL) at reflux for 18 h. Upon cooling, the reaction mixture was concentrated to form a yellow viscous oil and washed with Et2O (3 ¡Á 40 mL). The resulting oil was then dissolved in H2O (40 mL). LiTf2N (2.26 g, 7.87 mmol) was added, and then the resulting mixture stirred at room temperature for 12 h. A yellow oil was then extracted from this aqueous mixture with CH2Cl2 (3 ¡Á 50 mL). The CH2Cl2 layer was then washed with H2O (3 ¡Á 100 mL), dried over anhydrous MgSO4, filtered, and concentrated to give monomer 2c as a light yellow oil (yield: 3.49 g, 88%). 1H NMR (300 MHz, CDCl3): delta8.88 (s, 1H), 7.44 (d, J = 8.2 Hz, 2H), 7.33 (d, J = 8.2 Hz, 2H), 7.24 (dt, J = 12.0, 2.0 Hz, 2H), 6.69 (dd, J = 17.6, 10.9 Hz, 1H), 5.78 (d, J = 17.6, 1H), 5.31 (d, J = 10.8, 1H), 5.31 (s, 2H), 4.16 (t, J = 7.4 Hz, 2H), 1.93-1.76 (m, 2H), 1.39-1.17 (m, 14H), 0.87 (t, J = 7.0 Hz, 3H). 13C NMR (75 MHz, CDCl3): delta139.19, 135.83, 135.58, 131.69, 129.29, 127.41, 122.45, 122.24, 122.08, 117.82, 115.76, 53.46, 50.49, 31.95, 30.18, 29.51, 29.40, 29.34, 28.96, 26.24, 22.77, 14.21. IR (neat): 3146.88, 2927.24, 2856.85, 1560.77, 1456.43, 1348.21, 1182.03, 1133.87, 1053.89, 990.02, 914.86, 830.80, 788.70, 739.55, 653.29. HRMS (ES) calcd. for C24H33F6N3O4S2 (M+ Tf2N-): 605.1817; observed: 605.2435. Since imidazolium-based ionic liquid compounds are known in the literature to have combustion issues for C, H, and N elemental analysis [34], the 1H and 13C NMR spectra for isolated 2c are provided in the Supplementary Data to help confirm its purity.

The synthetic route of 33529-02-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shi, Zhangxing; Newell, Brian S.; Bailey, Travis S.; Gin, Douglas L.; Polymer; vol. 55; 26; (2014); p. 6664 – 6671;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 144689-93-0, These common heterocyclic compound, 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-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.

18(a) Ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate 48 mg of sodium hydride (as a 55% w/w dispersion in mineral oil) were added to a solution of 0.26 g of ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate (prepared as described in Preparation 9) in 5 ml of N,N-dimethylformamide, and the resulting mixture was stirred at room temperature for 30 minutes. A solution of 0.72 g of 4-[2-(trityltetrazol-5-yl)phenyl]benzyl bromide in 5 ml of N,N-dimethylformamide was then added, and the reaction mixture was stirred at room temperature for 2 hours and then at 60 C. for 4 hours. At the end of this time, it was dissolved in ethyl acetate and the solution was washed three times with water. The solution was then dried over anhydrous sodium sulfate, after which it was freed from the solvent by distillation. The residue was purified by column chromatography through silica gel, using a 1:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 0.62 g of the title compound as an amorphous solid. This was crystallized from diisopropyl ether, to give the title compound as crystals, melting at 167-168 C. (with decomposition). Nuclear Magnetic Resonance Spectrum (CDCl3) delta ppm: 0.88 (3H, triplet, J=7 Hz); 1.08 (3H, triplet, J=7 Hz); 1.5-1.8 (2H, multiplet); 1.64 (6H, singlet); 2.52 (2H, triplet, J=8 Hz); 4.12 (2H, quartet, J=7 Hz); 5.38 (2H, singlet); 5.78 (1H, singlet); 6.7-7.6 (22H, multiplet); 7.8-8.1 (1H, multiplet).

The synthetic route of 144689-93-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sankyo Company, Limited; US5616599; (1997); 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. 870837-18-6, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde

Synthesis of (Z)-2-[1-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]methylidene]-4-(3,4,5-trifluorobenzyl)morpholin-3-one Thionyl chloride (16.1 mL) was added to a solution of 2-hydroxy-4-(3,4,5-trifluorobenzyl)morpholin-3-one (3.94 g) in methylene chloride, and the reaction solution was stirred at 50 C. for one hour. The reaction solution was concentrated under reduced pressure, and the residue was diluted with methylene chloride. Then, triphenylphosphine (5.2 g) was added under ice-cooling, and the reaction solution was stirred at room temperature for 4.5 hours. The reaction solution was concentrated under reduced pressure. Ethanol (64.6 mL), TEA (4.2 mL), and 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (2.72 g) were added to the residue, and the reaction solution was heated under reflux for two hours. The reaction solution was concentrated under reduced pressure, and the residue was diluted with 2 N aqueous hydrochloric acid and ethyl acetate. Then, the aqueous layer was separated. The organic layer was washed with 2 N aqueous hydrochloric acid. Then, the total aqueous layers were combined and made alkaline with a concentrated sodium hydroxide solution. The organic layer was separated by extraction from the alkaline solution with chloroform, and then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography using NH silica gel (heptane:ethyl acetate=1:1 to 0:100) to obtain 1.92 g of the title compound. 1H-NMR (CDCl3) delta (ppm): 2.34(s,3H), 3.56(t,J=4.8 Hz,2H), 3.87(s,3H), 4.28(t,J=4.8 Hz,2H), 4.66(s,2H), 6.93(s,1H), 6.95-6.99(m,3H), 7.23(d,J=8.0 Hz,1H), 7.40(dd,J=8.0,1.2 Hz,1H), 7.42(d,J=1.2 Hz,1H), 7.85(s,1H).

The synthetic route of 870837-18-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eisai R&D Management Co., Ltd.; US2007/117798; (2007); 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. 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, A new synthetic method of this compound is introduced below., HPLC of Formula: C12H20N2O3

Weigh 24.0 g of compound 1, 55.7 g of compound 2, And add 124g of potassium carbonate, Then 200 mL of butanone was added, Warmed to 60 C, Stir for two hours, Cool to 45 , The composite catalyst (a mixture of polyethylene glycol 400 and N, N-dimethylacetamide in a mass ratio of 5: 1) Continue stirring for 4 hours, TLC detection, Show two kinds of raw materials are not left. The reaction is over, filter, The filtrate was collected, concentrate, Get oil, A mixture of 50 mL of ethanol and water (2: 1 by volume) Stirring, A large number of solid precipitation, filter, Collect the solid, Washed with 50mL n-hexane beating, The target compound 67.3g, Yield 93.8% The HPLC purity was 99.3%.

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; Disha Pharmaceutical Group Co., Ltd.; Zhang Zhaoxing; Zhang Hongqiang; Qin Litai; Li Wei; Li Zongwen; Xia Haijian; (6 pag.)CN103012382; (2016); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 5993-91-9, name is (1H-Benzo[d]imidazol-2-yl)methanamine dihydrochloride, 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 5993-91-9, name: (1H-Benzo[d]imidazol-2-yl)methanamine dihydrochloride

Preparation 1 2-(Aminomethyl)benzimidazole; Add 2-(aminomethyl)bcnzimidazole, dihydrochloride, hydrate (18.50 g) to a solution of potassium hydroxide (9.50 g) in methanol (400 mL). Stir the resulting mixture at room temperature for 30 minutes, filter, and concentrate the filtrate in vacuo. Extract the residue with EtOAc (5 x 500 mL) and filter. Concentrate the filtrate in vacuo to give the title compound as a white solid (9.60 g).

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, (1H-Benzo[d]imidazol-2-yl)methanamine dihydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SCHERING CORPORATION; EP1135374; (2006); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 6154-30-9,Some common heterocyclic compound, 6154-30-9, name is 2,5-Dibromo-4-nitro-1H-imidazole, molecular formula is C3HBr2N3O2, 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 mixture consisting of 2, 5-dibromo-4- nitroimidazole (27.1 g, 100 mmol) and concentrated hydrochloric acid (434 ml) was stirred under heating (77C to 80C, 16 hours). The reaction mixture was left to cool, and then stirred under cooling on ice (5C to 10C, 2 hours). Thereafter, the precipitated crystals were collected by filtration and air-dried (50C, 5 hours). The yield of the dried product was 8.26 g. The filtrate was further extracted with ethyl acetate (300 ml) and then dried (MgSO4), followed by vacuum concentration and exsiccation. The yield of the exsiccated product was 9.63 g. Thus, 17.9 g (in total) of 2, 5-dichloro-4-nitroimidazole was obtained (yield: 98. 3%). IR (KBr) : 1566,1475, 1403,1366, 1332,1272, 1190, 1091,996, 834,679 cm-l. MS (70 eV) m/z (relative intensity): 183 (15, M+), 181 (25), 108 (28), 74 (42), 62 (100).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,5-Dibromo-4-nitro-1H-imidazole, its application will become more common.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; WO2005/77913; (2005); A1;,
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. 3543-73-5, name is Ethyl 4-(5-amino-1-methyl-1H-benzo[d]imidazol-2-yl)butanoate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C14H19N3O2

[0079] To a solution of 81.3 g (650.6 mmol) 2-bromoethanol, 1 g potassium iodide and 100 g water was added 17.0g (65 mmol) compound (6). The reaction mixture was heated to 65-70 C and held at this temperature for 8 h to 12 h.The pH value of the solution was held between 4.2-5.5 during this period by dropwise addition of a solution of 20.0 g(151.4 mmol) diammonium hydrogen phosphate in 35 g water. The control of pH over the duration of the reaction waseffected through use of a pH electrode. The conversion was followed by HPLC. The reaction was continued until thefraction of compound (7A) was ? 1.5 %. Thereby ca. 8% of compound (7B) had formed and the proportion of compound(7) was ca. 87%. The reaction mixture was subsequently concentrated to dryness at ca. 55-60 C under vacuum. Tothe residue was added 150 g water and, preferably with an alkali metal carbonate, the pH value adjusted to ca. 8.5. Thedesired product (7) was extracted with 200 g methylene chloride or 225 g chloroform, and the organic phase subsequentlywashed with 60 – 80 g water. The organic phase was then concentrated to dryness and the remaining oil or alreadycrystalline residue dissolved in 200 g ethyl acetate or alternatively in 60 g actetonitrile. Compound (7) crystallised at ca.5 C and was filtered under suction, washed with 20 g cold ethyl acetate or alternatively with 15 g cold acetonitrile anddried at 60 -70 C. The yield of compound (7) was 18.3 g (52.4 mmol) with a content of ? 98.2% (80.5 % of theory). Thecrude product contained ?0.6% compound (7A) and compound (7B) respectively as well as <0.15% of compound (7C).0082] Analogous to Example 4 but with use of 9.0 g (65 mmol) potassium carbonate dissolved in 12 g water to holdthe pH value between 4.2 - 5.5. Identical results in terms of yield and quality.[0084] This example is a scaled-up analogue of Example 6 with use of 340 g (1.3 mol) compound (6), 2000 ml waterand 1625 g (13 mol) 2-bromoethanol. The reaction was performed without potassium iodide at 69 - 70C.. The pH valuewas held between 4.2 - 5.5 using a solution of 138 g sodium carbonate (1.3 mol) in 500 g water. Until a content ofcompound (7A) of ?1.5% was reached, the duration of the reaction was 13.5 h. The yield of compound (7) was 365 gcrude and 343.5 g after recrystallisation from acetonitrile (75.6% of theory). According to the analysis of related databases, 3543-73-5, the application of this compound in the production field has become more and more popular. Reference:
Patent; HEYL Chemisch-Pharmazeutische Fabrik GmbH und Co. KG; Frey, Michael; Walther, Dirk-Detlef; EP2690096; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem