Author: Jessica.F

Adding a certain compound to certain chemical reactions, such as: 3012-80-4, name is 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde, 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 3012-80-4, Recommanded Product: 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde

Synthesis Example 6-1: Synthesis of 2-(4-(N-Boc-N-2-picolylamino methyl) benzoyl)-5-((1-methylbenzimidazol-2-ylmethyl) amino) valerate 1-naphthalenemethylamide (Compound XIII-6) 50.3 mg of the compound synthesised in Synthesis Example 1-4 was dissolved in 1 ml of anhydrous methanol, and then 16.1 mg of 1-methyl-2-formylbenzimidazole was added to the solution and the resultant mixture was stirred for 1.5 hours at room temperature. After the solvent was distilled off, 1 ml of anhydrous methanol and a drop of acetic acid were added to the resultant and the resultant mixture was cooled to 0°C. Subsequently, 14.2 mg of sodium borohydride was added thereto and the resultant mixture was stirred for 0.5 hour at room temperature. The residue obtained by concentrating the reaction solution was purified by means of silica gel column chromatography (2.5 g, chloroform/methanol = 15/1), and 31.3 mg of the above-mentioned compound was obtained as a white solid product. MS(FAB,Pos.):m/z=740[M+1]+ 1H-NMR(500MHz,CDCl3):delta=1.43 and 1.44(9H,2s),1.52-1.63(1H,m), 1.65-1.78(1H,m),1.89-2.01(2H,m),2.68-2.83(2H,m),3.58(3H,s),3. 75(1H,d,J=14.6Hz),3.81(1H,d,J=14.6Hz),4.41and4.44(2H,2s),4.52 and 4.55(2H,2s)4.69-4.75(1H,m),4.85(1H,dd,J=14.6,5.1Hz),4.98 (1H,dd,J=14.6,5.6Hz),7.10-7.35(7H),7.36(1H,d,J=6.6Hz),7.43-7. 51(2H,m),7.52-7.60(1H,m),7.69-7.78(7H,m),7.80-7.83(1H,m),7.99 -8.01 (1H,m), 8.53 (1H,ddd,J=4.9,2.0,1.0Hz).

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; Kureha Chemical Industry Co., Ltd.; EP1389460; (2004); 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. 104619-51-4, name is Di(1H-imidazol-1-yl)methanimine, A new synthetic method of this compound is introduced below., Formula: C7H7N5

A solution of Intermediate 32 (260 mg, 0.470 mmol) in DMSO (2 mL) was treated with di(lH-imidazol-l-yl)methanimine (151 mg, 0.939 mmol) and the mixture was stirred until all of the latter had dissolved. Stirring was then continued for a further 3 h and the mixture was allowed to stand at RT overnight. The mixture was diluted with ethyl acetate and the solution was washed with water. The aqueous was further extracted with ethyl acetate and the combined organics were washed with brine, dried (MgS04) and evaporated. The product was purified on a 5 g Si cartridge eluting with 1 : 1 ethyl acetate in DCM to give the desired product (180 mg). LCMS (Method 4): Rt = 1.55 min, m/z 579.5 [M+H]+

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; CHIESI FARMACEUTICI S.P.A.; ACCETTA, Alessandro; RANCATI, Fabio; CLARK, David Edward; EDWARDS, Christine; (113 pag.)WO2019/238628; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 104619-51-4, 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. 104619-51-4, name is Di(1H-imidazol-1-yl)methanimine, This compound has unique chemical properties. The synthetic route is as follows.

Example 28: r4-(5-Amino- H .3.41 oxadiazol-2-yl)-6-ethvnyl-pyridin-3-v?-(2-fluoro-; To a solution of 2-Ethynyl-5- (2-fluoro-4-iodo-phenylamino)-isonicotinic acid hydrazide (124mg, 0.31 mmol, 1eq) in DMSO (2mL) C- (Di-imidazol-i-yl)-methyleneamine (101mg, 0.63mmol, 2eq) was added. The reaction mixture was stirred at RT under argon overnight, and then poured into water. The solid fomed was isolated by filtration and washed with methanol to afford the product (30 mg). LC/MS (Method A) [5.15min; 422(M+1 )]

The chemical industry reduces the impact on the environment during synthesis Di(1H-imidazol-1-yl)methanimine. I believe this compound will play a more active role in future production and life.

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

These common heterocyclic compound, 106429-57-6, name is Methyl 2-oxo-2,3-dihydro-1H-benzo[d]imidazole-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. Product Details of 106429-57-6

2-oxo- 2,3-dihydro-1 /-/-benzoimidazole-5-carboxylic acid methyl ester (3.00 g, 15.6 mmol) and phosphorus oxychloride (30 ml_) were combined and heated to 100 0C for 48 h. The mixture was cooled to 23 0C and concentrated under reduced pressure. The residue was cooled to 0 0C, and cold, saturated aqueous NaHCO3 (60 ml_) was added cautiously. After stirring at 23 0C for 15 min, the mixture was sonicated and the resulting residue was filtered to yield the titled compound (3.13 g, 95%), which was used in the next step without further purification. MS (ESI/CI): mass calcd. for C9H7CIN2O2, 210.02; m/z found, 211.0 [M+H]+.

The synthetic route of Methyl 2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; WO2009/134750; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 17228-38-5, 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. 17228-38-5, name is N-Methyl-1H-benzo[d]imidazol-2-amine, This compound has unique chemical properties. The synthetic route is as follows.

2-((5R,8aS)-3-Chloro-5-methyl-5,6,8a,9-tetrahydro-8H-7, 1 0-dioxa-2,4,4b-triaza-phenanthren-1 -yl)-propan-2-ol (154,51 mg; 0,500 mmol; 100,00 mol%), (1H-benzimidazol-2-yl)-methyl-amine (73,59 mg; 0,500 mmol; 100,00 mol%), tris(dibenzylideneacetone)dipalladium(0) (91,57 mg; 0,100 mmol; 20,00 mol%) and dicyclohexyl-(2?,4?,6?-triisopropyl-biphenyl-2-yl)-phosphane (95,34 mg; 0,200 mmol; 40,00 mol%) were dissolved in dioxane (1,36 ml; 15,845 mmol;31 69,00 mol%), lithium tert-butoxide (1,0 M solution in tetrahydrofuran)(700,00 p1; 0,700 mmol; 140,00 mol%) was added and the mixture was stirredfor 1 h at 80 00. The reaction mixture was purified by column chromatography(petroleum benzene I ethyl acetate) to afford the product as yellow solid(14.8mg, 6.5%); LCMS (method C): 1 .29 mm (purity 89.6%); [MH+] 411 .3 mlz;1H NMR (400 MHz, DMSO-d6)o 13.08 (5, 1H), 7.42 (d, J 7.1 Hz, 1H), 7.37-7.23 (m, 1 H), 7.16-7.00 (m, 2H), 5.37 (5, 1 H), 4.69-4.57 (m, 1 H), 4.35 (dd,J = 10.9, 3.2 Hz, 1 H), 3.97 – 3.84 (m, 2H), 3.81 (d, J = 11 .5 Hz, 1 H), 3.74 -3.71 (m, 1 H), 3.65 (dd, J = 11 .6, 3.3 Hz, 1 H), 3.29 (5, 3H), 3.23 – 3.09 (m, 1 H),1 .52 (5, 3H), 1 .51 (5, 3H), 1 .27 (d, J = 6.8 Hz, 3H).

The chemical industry reduces the impact on the environment during synthesis N-Methyl-1H-benzo[d]imidazol-2-amine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK PATENT GMBH; BURGDORF, Lars; DORSCH, Dieter; TSAKLAKIDIS, Christos; (189 pag.)WO2017/202748; (2017); 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. 57531-37-0, name is 2-Chloro-5-nitroimidazole, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-Chloro-5-nitroimidazole

Example 3 Preparation of 2-chloro-1-(2,3-dihydroxy-2-methylpropyl)-4-nitroimidazole 2-Chloro-4-nitro-1H-imidazole (6.78 g, 46 mmol) and 2-methyloxiran-2-ylmethyl 4-nitrobenzoate (12 g, 51 mmol) were dissolved in ethyl acetate (24 ml), and triethylamine (1.3 ml, 9.2 mmol) was added to the solution. The resulting mixture was stirred under reflux for 14 hours. The reaction mixture was concentrated under reduced pressure, and methylene chloride (40 ml) was added to the residue. The resulting precipitates were filtered off, and dissolved in methanol (120 ml). To the solution, potassium carbonate (318 mg, 2.3 mmol) was added, and the resulting mixture was stirred at room temperature for 1 hour. To the resulting mixture, 6 N hydrochloric acid (0.8 ml) and magnesium sulfate (8 g) were added in this order with cooling on ice-bath, and the resulting mixture was stirred for 30 minutes. Insoluble matters were removed by filtration through Celite, and the filtrate was concentrated under reduced pressure. To the residue, ethyl acetate (6 ml) and toluene (60 ml) were added. The resulting precipitates were filtered off and dried at 50C to afford 2-chloro-1-(2,3-dihydroxy-2-methylpropyl)-4-nitroimidazole (7.88 g, yield 72%) as a white powder. 1H-NMR (DMSO-d6) deltappm: 1.02 (3H, s), 3.25 (2H, d, J = 5.3 Hz), 4.04 (2H, s), 4.98 (1H, s), 5.10 (1H, t, J = 5.4 Hz), 8.29 (1H, s).

According to the analysis of related databases, 57531-37-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; EP1555267; (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. 152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole

To a 100 mL flask was added 2-n-propyl-4-methyl-6- (1′-methylbenzimidazol-2-yl) benzimidazole1.0 g (3.3 mmol), N-methylpyrrolidone4 g of potassium tert-butoxide and 0.4 g (3.6 mmol) of potassium tert-And stirring was started with a magnetic stirrer.While cooling to below 10 C.,A solution of 1.2 g (3.5 mmol) of 4′-bromomethylbiphenyl-2-carboxylic acid tert-butyl ester dissolved in 4.1 g of N-methylpyrrolidone was added dropwise over 2 hours. After the dropwise addition, the mixture was stirred at an internal temperature of 0 to 10 C. for 2 hours. As a result of sampling the reaction solution and conducting liquid chromatography analysis, it was found that 2 – n – propyl – 4 – methyl – 6 – (1 ‘- methylbenzimidazol – 2 – yl) benzimidazole was not detected and 4’ – [[4- Methyl-6- (1-methyl-1 H-benzimidazol-2-yl) -2-propyl- 1 H- benzimidazol- 1 – yl] methyl] biphenyl-2-carboxylic acid tert-butyl ester was 86.0% Area percentage) was generated.

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 152628-02-9.

Reference:
Patent; DNP FINE CHEMICALS UTSUNOMIYA COMPANY LIMITED; MATSUMOTO, TAKAFUMI; IKEDA, SHIN; SUZUKI, YOSHINOBU; (12 pag.)JP5711888; (2015); B2;,
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

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

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