Category: imidazoles-derivatives

Synthetic Route of 1402838-08-7,Some common heterocyclic compound, 1402838-08-7, name is 2-(1-Trityl-4-imidazolyl)benzaldehyde, molecular formula is C29H22N2O, 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.

Dimethyl (2-(6-fluoro-2-(2-hydroxypropan-2-yl)benzofuran-5-yl)-2-oxoethyl)phosphate (0207-60) (400 mg, 1.47 mmol, 3.3 eq),2-(1-trityl-1H-imidazol-4-yl)benzaldehyde (0105-1) (180 mg, 0.44 mmol, 1.0 equiv) andCesium carbonate (958 mg, 2.94 mmol, 2.0 eq.)Added to 40 ml of isopropanol,Stir the reaction overnight at room temperature,Concentrate under reduced pressure, add ethyl acetate and water, separate, dry over anhydrous sodium sulfate, and concentrate under reduced pressure to obtain 1-(6-fluoro-2-(2-hydroxypropan-2-yl)benzofuran-) as a yellow solid. 5-base)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one (540 mg, crude)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(1-Trityl-4-imidazolyl)benzaldehyde, its application will become more common.

Reference:
Patent; Guangzhou Bi Beite Pharmaceutical Co., Ltd.; Cai Xiong; Qian Changgeng; Weng Yunwo; Qing Yuanhui; Liu Bin; Lin Mingsheng; Wang Yanyan; (126 pag.)CN107383024; (2017); A;,
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Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 28890-99-5, name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, molecular formula is C13H9N3, 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. HPLC of Formula: C13H9N3

5/-/-Benzo[c/]benzo[4,5]imidazo[1 ,2-a] imidazole (15.0 g, 72.4 mmol), 4-iodo- 1 ,1 ‘-biphenyl (20.3 g, 72.4 mmol), K3P04 (46.1 g, 217 mmol) and copper(l) iodide (2.76 g, 14.5 mmol) are suspended in 1 ,4-dioxane (750 ml) under argon. The mixture is degassed and heated up to 100 C while stirring. trans- 1 ,2-Diaminocyclohexane (75 ml) is added and stirring at 100 C is continued for four days. Then, the reaction mixture is cooled to room temperature and 5% ammonia in water (600 ml) is added. The precipitate is filtered off. The solid is washed with 5% ammonia in water, pure water, ethanol and heptane. The crude product is dried in vacuo. A grey powder (23 g, 64.0 mmol, 88%) is obtained. (0201) GC-MS (El, 70 eV) = 359 (100%) Synthesized accordingly are the following products using the respective starting materials (SM):

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 28890-99-5, its application will become more common.

Reference:
Patent; MERCK PATENT GMBH; STENGEL, Ilona; MAIER-FLAIG, Florian; HARBACH, Philipp; MONTENEGRO, Elvira; LUDEMANN, Aurelie; (0 pag.)WO2019/170691; (2019); A1;,
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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. 7189-69-7, name is 1,1′-Sulfonyldiimidazole, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 7189-69-7

A solution of 1,1?-sulfonyldiimidazole(119 mg, 0.6 mmol), ethinyl estradiol (9,89 mg, 0.3 mmol), and cesium carbonate (49 mg, 0.15 mmol) in 5 mL of tetrahydrofuran was stirred at 23 C for 18 h, and then was concentrated. The residue was dissolved in 5 mL of ethyl acetate, which was washed sequentially with saturated aqueous ammonia chloride, and brine, dried, concentrated, and then chromatographed on silica with 2:3 ethyl acetate / hexane as the eluant, to provide 116 mg(91%) of 10 as a white solid, mp 168- 170 C : 1H NMR (500 MHz, CDCl3) delta 7.74 (s,1 H), 7.32 (d, 1 H, J = 1.5 Hz), 7.24(d, 1 H, J = 9.5 Hz), 7.17 (s, 1 H), 6.63 (d, 1 H, J = 6.5 Hz),6.60 (d, 1 H, J = 1.5 Hz), 2.80 (d, 2H, J = 4.5 Hz), 2.59 (s, 2 H), 2.39 – 2.28 (m, 2 H), 2.24 – 2.18 (m, 1H), 2.08 – 1.97 (m, 1 H), 1.97 – 1.84 (m, 2 H), 1.84 – 1.59 (m, 3 H), 1.54 -1.22 (m, 4 H), 0.88 (s, 3 H); 13C NMR (126 MHz, CDCl3) delta147.1, 141.2, 139.7, 137.8, 131.4, 127.4, 121.3, 118.6, 118.2, 87.6, 79.9, 74.3, 49.7, 47.2, 43.9, 39.1, 38.9, 32.9, 29.7, 26.9, 26.3,23.0, 12.9; ESI-MS m/z 427.1 MH+.

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 7189-69-7.

Reference:
Article; Yang, Baocheng; Sun, Zhexun; Liu, Changzhi; Cui, Yan; Guo, Zhilei; Ren, Yuwei; Lu, Zhijian; Knapp, Spencer; Tetrahedron Letters; vol. 55; 49; (2014); p. 6658 – 6661;,
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Related Products of 21252-69-7, A common heterocyclic compound, 21252-69-7, name is 1-Octyl-1H-imidazole, molecular formula is C11H20N2, 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.

Synthesis of 1-octyl-3(propyl-3-sulfonyl) imidazolium 1 equivalent of 1 -octyl-imidazole was reacted with 1 equivalent of propanesultone at reflux temperature in 10percent toluene as solvent. After 10 hours, the mixture was cooled down at room temperature and then filtrated. The cake was washed with 3 portions of toluene before drying under high vacuum at 60°C.

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; ECOLE D’INGENIEURS ET D’ARCHITECTES DE FRIBOURG; MARTI, Roger; VANOLI, Ennio; AEBY, Sandrine; FISCHER, Fabian; HAPPE, Manuel; WO2013/8172; (2013); A1;,
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Imidazole | C3H4N2 – PubChem

4887-88-1, name is 5-Bromo-1H-benzo[d]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. Application In Synthesis of 5-Bromo-1H-benzo[d]imidazole

[00512] A. tert-Butyl S-bromo-lH-benzofcphimidazole-l-carboxylate. 5-Bromo- l H-benzo[d] imidazole (0.300 g, 1.52 mmol), di-tert-butyl dicarbonate (0.397 g, 1.82 mmol), triethyl amine (0.307 g, 3.04 mmol) and tetrahydrofuran (10 mL) were stirred at 25 C for 18 h. The solution was condensed under reduced pressure and the product was isolated using Biotage silica gel chromatography (0-80% ethyl acetate in hexanes). Fractions containing product were concentrated to give (0.398 g, 88% yield). MS (ESI) m/z 298 [M+ 1]+.

The synthetic route of 4887-88-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; WO2008/51493; (2008); A2;,
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Imidazole | C3H4N2 – PubChem

Reference of 5400-75-9, These common heterocyclic compound, 5400-75-9, name is 5-Methyl-1H-benzo[d]imidazol-2(3H)-one, 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.

5-Methyl-1 ,3-diotahydro-2H-benzimiotadazol-2-one (13.1 g, 88.5 mmol) and phosphorus oxychloride(130 rmL, freshly distillated) was charged into three-neck round-bottom flask. The mixture was heated up to boiling point till homogeneous solution was formed. After that the dried hydrogen chloride was bubbled through inlet gas-pipe into the reaction mixture. The mixture was boiled for 15 hours. Excess of phosphorus oxychloride was distillated in vacuo. Mixture of ice and water (250 ml_) was added to residue. The obtained suspension was cooled to room temperature and filtered. Filtrate was alkalinized by aqueous ammonia solution till pH 8, cooled by cold water and filtered crude 2-chloro-6-methyl-1H- benzimidazole. White powder was crystallized from aqueous methanol (water-methanol: 1.1 , 200 mL), washed by aqueous methanol and dried in desiccator under Phosphorous oxide in vacuo. Yield. 8.17 g (55 percent).

Statistics shows that 5-Methyl-1H-benzo[d]imidazol-2(3H)-one is playing an increasingly important role. we look forward to future research findings about 5400-75-9.

Reference:
Patent; CRYSOPTIX K.K.; WO2009/109782; (2009); 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. 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, A new synthetic method of this compound is introduced below., SDS of cas: 33543-78-1

General procedure: A mixture of 0.68 g of imidazole, 2.13 g of oxidant(chloramine-B) in presence of 2.5 cm3 (0.01 mol dm-3) of aqueous perchloric acid was stirred at 303 K for 8?10 h. After completion of the reaction (monitored by TLC), the reaction products were neutralized with alkali and extracted with ether. The organic products were subjected to spottests and chromatographic analysis (TLC technique). Further, the reaction mixture was extracted with ethyl acetate and dried over sodium sulfate. The solvent was evaporated under reduced pressure to obtain crude products. The crude products were purified on silica gel column by using petroleum ether and ethyl acetate as solvents to get the pure products. Above analyses revealed the formation of corresponding imidazolones as the oxidation products of imidazoles. 3,5-Dihydroimidazol-4-one, 2-methyl-3,5-dihydroimidazol-4-one, 2-ethyl-3,5-dihydroimidazol-4-one,3,5-dihydro-4-oxoimidazol-2-carbaldehyde, and 3,5-dihydro-4-oxoimidazol-2-ester are the oxidation products of1H-imidazole, 2-methyl-1H-imidazole, 2-ethyl-1H-imidazole,1H-imidazole-2-carbaldehyde, and 1H-imidazole-2-ester, respectively. The mass spectra showed a molecularion peak at m/z = 84 amu (Fig. 1), 99 amu (M 1,Fig. 2), and 112 amu (Fig. 3), clearly confirming 3,5-dihydroimidazol-4-one, 2-methyl-3,5-dihydroimidazol-4-one, and 2-ethyl-3,5-dihydroimidazol-4-one as oxidation products of 1H-imidazole, 2-methyl-1H-imidazole, and2-ethyl-1H-imidazole, respectively. Further these productswere confirmed by NMR data (supplementary material,Figs. 1s?3s). Furthermore, we have succeeded in estimating the products, imidazolones, in case of all the five imidazoles. In some typical experiments, the weight of imidazolones and their percentage yield obtained are recorded in Table 1. The recovery of imidazolones was 87?93 percent yields. Further no reaction was noticed between oxidation products and CAB under prevailing experimental conditions.

The synthetic route of 33543-78-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Manjunatha; Puttaswamy; Monatshefte fur Chemie; vol. 147; 9; (2016); p. 1517 – 1529;,
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Imidazole | C3H4N2 – PubChem

Electric Literature of 616-47-7, 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 616-47-7 as follows.

To a solution of N-methylimidazole (1.64 g, 19.97 mmol) and sodium acetate (25 g, 300 mmol) in acetic acid (180 mL) at room temperature was added bromine (9.6 g, 60.07 mmol) dropwise as a solution in 20 mL acetic acid. The resulting mixture was stirred for 2.5 h at room temperature. Acetic acid was removed in vacuo, the residue was suspended in 500 mL water and stirred at room temperature for 10 minutes. The resultant precipitate was filtered, washed with water and dried under high vacuum to give 2,4,5-tribromo-l-methyl- lH-imidazole (1.82 g, 29% – some product remained in the mother liquor) as a light yellow powder. Used without further characterization. To a suspension of the tribromide (1.82 g, 5.71 mmol) in 45 mL water was added sodium sulfite (13 g, 103 mmol) and the resulting mixture was stirred at rapid reflux for 24 h. After cooling to room temperature, organics were extracted with ether (3 chi 75 mL), dried over magnesium sulfate, filtered and concentrated to give 1.61 g of a mixture of tri-, di- and monobromoimidazoles. This mixture was re-subjected to the reduction conditions (same quantity of sodium sulfite) using 15 mL of 3: 1 water/acetic acid as solvent and heating in a sealed vessel at 130 C for 60 h. After cooling to room temperature, the pH of the reaction mixture was adjusted to 9-10 by addition of 2 N sodium hydroxide. Organics were extracted with ether (3 chi 50 mL), dried over magnesium sulfate, filtered and concentrated to give crude 4-bromo-l -methyl- lH-imidazole (571 mg, ca. 62%). Used without further characterization.. 4-Butyl-l -methyl- lH-imidazole (95 mg, 22 %) was synthesized as in Example 3.1 using 4-bromo-l -methyl- lH-imidazole (571 mg, ca. 3.53 mmol) in place of 5-bromo-2- formylfuran and propylboronic acid (372 mg, 4.24 mmol) in place of hexylboronic acid. Used without further characterization. To a solution of diisopropylamine (0.13 mL, 0.918 mmol) in 2 mL anhydrous tetrahydrofuran at – 0C was added -butyllithium (0.34 mL, 2.5 M in hexanes) dropwise. The solution was stirred while warming to -20 C over 20 minutes. After cooling to -78 C, 4-butyl-l -methyl- lH-imidazole (95 mg, 0.765 mmol) was added dropwise as a solution in 2 mL anhydrous tetrahydrofuran. The resulting solution was stirred for 40 minutes at -78 C. Dimethylformamide (0.24 mL, 3.06 mmol) was added and the solution stirred while warming to room temperature. The reaction mixture was poured into 15 mL of 1 N hydrochloric acid and stirred for 5 minutes. The pH of the reaction mixture was adjusted to 7-8 by careful addition of saturated sodium bicarbonate solution. Organics were extracted with dichloromethane (3 chi 20 mL), dried over magnesium sulfate, filtered and concentrated. The crude residue was subjected to chromatography on silica gel with gradient elution (5-50% ethyl acetate in hexanes) to give l -methyl-4-propyl-lH-imidazole-2-carbaldehyde (9 mg, 8%) as an off-white solid. Used without further characterization

According to the analysis of related databases, 616-47-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY; PROVID PHARMACEUTICALS INC.; EBRIGHT, Richard H.; EBRIGHT, Yon W.; SHEN, Juan; BACCI, James; HIEBEL, Anne-Cecile; SOLVIBILE, William; SELF, Christopher; OLSON, Gary; WO2013/192352; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 98873-55-3, name is 2-(1H-Imidazol-1-yl)acetonitrile, 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. HPLC of Formula: C5H5N3

A 25 mL flask is charged with powdered KOH (211 mg, 3.23 mmol), DMSO (3 mL), purged with Argon and is cooled at 10CC with a water bath. A solution of 2-imidazol-1-ylacetonitrile (166 mg, 1.55 mmol) and CS2 (0.195 mL, 3.23 mmol) in DMSO (3 mL) is then added slowly to give an orange mixture. The cooling bath is removed and the reaction is stirred at room temperature for 30 minutes. A solution of [2-chloro-1-(2,5-dichloro-3-thienyl)ethyl] methanesulfonate (400 mg, 1.29 mmol) in DMSO (2 mL) isthen added dropwise. After 30 minutes, the reaction mixture is poured into H20 (15 mL). The aqueous phase is extracted with dichloromethane, the combined organic phases are washed with brine, dried with Na2504, filtered and evaporated to give a crude pale yellow residue. Purification by chromatography on silica gel (heptanes Iethyl acetate, 5:1-* 1:1 -* 1:3) afford (2E)-2-[4-(2,5-dichloro- 3-thienyl)-1,3-dithiolan-2-ylidene]-2-imidazol-1-yl-acetonitrile (Compound l.h.25) as a white solid. Mp =117-1 19CC. 1H-NMR (400 MHz, CDCI3): oe = 7.63 (s, 1H), 7.18 (s, 1H), 7.05 (t, J = 1.3 Hz, 1H), 6.96 (s,1H), 5.39 (dd, J= 5.2, 8.7 Hz, 1H), 3.74 (dd, J= 5.2, 11.9 Hz, 1H), 3.63 (dd, J= 8.7, 11.9 Hz, 1H). MS (ESI): m/z= 360, 362 (M+1).

The synthetic route of 2-(1H-Imidazol-1-yl)acetonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; GAGNEPAIN, Julien Daniel Henri; MAITY, Pulakesh; JEANMART, Stephane Andre Marie; LAMBERTH, Clemens; WO2015/162269; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 104619-51-4,Some common heterocyclic compound, 104619-51-4, name is Di(1H-imidazol-1-yl)methanimine, molecular formula is C7H7N5, 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.

Example 35: r4-(5-Amino- Pl .3.41 oxadiazol-2-yl)-pyridin-3-vn-f4-bromo-2-chloro- phenvU-amine; To a solution of 3-(4-Bromo-2-chloro-phe?ylamino)-iso?icotinic acid hydrazide (200mg, 0.59mmol, 1eq) in DMSO (2mL) C- (Di-imidazol-i-yl)-methyleneamine (188mg, 1.17mmol, 2eq) was added. The reaction mixture was stirred at RT under argon overnight and then poured into water. A solid precipitated out that was filtered and washed with methanol to give the desired product (125 mg). LC/MS (Method A) [4.77min; 367(M+1)]

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Di(1H-imidazol-1-yl)methanimine, its application will become more common.

Reference:
Patent; APPLIED RESEARCH SYSTEMS ARS HOLDING N.V.; WO2007/123936; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem