Author: Jessica.F

Related Products 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.

[402] To a solution of compound 1.1 (500 mg, 1.2 mmol) and 1-(adamantan-1-yl) ethanone (235 mg, 1.3 mmol) in a mixed solvent of ethanol (5 mL) and THF (5 mL) was added sodium ethoxide (122 mg, 1.8 mmol). The resulted mixture was stirred at room temperature for overnight, then the mixture was added water (30 mL), and extracted with ethyl acetate (60 mLx2). Then the combined organic phase was washed with brine, dried oversodium sulfate, filtered and concentrated. The residue was purified by column chromatography on silica gel (petroleum ether: ethyl acetate= 2:1) to afford compound 1.2 (400 mg, yield: 62%) as a white solid.[403] m/z: [M+H] 575

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; SHANGHAI DE NOVO PHARMATECH CO.,LTD.; LI, Qun; GAO, Daxin; (158 pag.)WO2016/131380; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 822-36-6, 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. 822-36-6, name is 4-Methyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows.

4-Fluoro-3-methoxybenzaldehyde (85 g, 0.55 mol), 4-methyl-1 /-/-imidazole (90.5 g,1.1 mol) and cesium carbonate (268.8 g, 0.82 mol) were combined in dimethylformamide (1.7 L) and stirred at 100 0C for 1 hour. The mixture was cooled to room temperature, filtered, and the filtrate was concentrated in vacuo. The residue was dissolved in water (2 L) and extracted with ethyl acetate (3 x 2 L). The combined organic layers were washed with water and brine, dried over sodium sulfate, and concentrated under reduced pressure. Chromatography on silica (Eluant: 2:1 petroleum ether: ethyl acetate) afforded a yellow solid, which was recrystallized from ethyl acetate (300 mL) to provide the title compound as a white solid. Yield: 17.8 g, 0.082 mol, 15%. 1H NMR (300 MHz, CDCI3) delta 2.31 (d, J=1.0 Hz, 3H), 3.97 (s, 3H), 7.01 (m, 1H), 7.45 (d, J=7.8 Hz, 1 H), 7.54-7.58 (m, 2H), 7.83 (d, J=1.3 Hz, 1 H), 10.01 (s, 1 H).

The chemical industry reduces the impact on the environment during synthesis 4-Methyl-1H-imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; PFIZER INC.; ALLEN, Martin, Patrick; AM ENDE, Christopher, William; BRODNEY, Michael, Aaron; DOUNAY, Amy, Beth; JOHNSON, Douglas, Scott; PETTERSSON, Martin, Youngjin; SCHWARZ, Jacob, Bradley; TRAN, Tuan, Phong; WO2010/100606; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 4856-97-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 4856-97-7 name is (1H-Benzoimidazol-2-yl)methanol, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Starting from the o-phenylenediamine compound (1.0equiv) and glycolic acid (2.0equiv), the reaction was refluxed in the presence of a 4.0 mol/L aqueous hydrochloric acid solution, and the TLC was traced until the reaction of the starting material was complete, and the reaction solution was cooled. To room temperature,Adjusting the pH to 7 with 20% NaOH, standing to precipitate a solid, suction filtration, and drying to obtain compound 5; transferring compound 5 to a round bottom flask,Add NaOH aqueous solution,KMnO4 (2.5 equiv) was added in portions at 80 C with stirring, and the reaction was continued after the addition.After all the raw materials were completely reacted, the reaction solution was cooled to room temperature, and the filtrate was filtered by suction.Adjust the pH to neutral with 20% aqueous HCl solution to precipitate a solid.Drying by suction filtration to obtain compound 6;Compound 6 with DMF(1.0equiv) dissolved, then added 1-hydroxybenzotriazole (HOBt, 1.1equiv)And 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI, 1.1 equiv),The reaction was stirred at room temperature for 30 min, and then compound 4 (1.1 equiv) was added to the reaction solution.Continue to stir the reaction,The TLC traces to the completion of the reaction of the starting material, and the reaction solution is poured into ice water.It was then extracted with ethyl acetate and the organic layer was evaporated.The crude product was purified by column chromatography to give the allyl intermediates Sb.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (1H-Benzoimidazol-2-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; Sun Yat-sen University; Qiu Liqin; Jiang Xiaoding; (74 pag.)CN109336887; (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. 75370-65-9, name is 4-Amino-1H-benzo[d]imidazol-2(3H)-one, A new synthetic method of this compound is introduced below., category: imidazoles-derivatives

Amine 2ah (1.34g, 6mmol) was dissolved in 20 ml of AcOEt and at 0C triphosgene (1.78 g, l equiv.) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 10 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound la (900 mg, 6 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt). The solvent was evaporated and the crude was dissolved in AcOEt (50 ml) and washed with water (1 X 40 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 750 mg of a white solid. Yield = 31% ‘HNMR (DMSO, 200 MHz) delta 1.58 (2H, m), 1.66 (4H, m), 2,78 (4H, M), 4.32 (2H, d, J = 6 Hz), 6.63 (1H, dd), 6.73 (1H, t), 6.94 (1H, t), 6.95 (1H, dd), 7.06 (2H, m), 7.29 (1H, d), 8.35 (1H, bs), 10.05 (1H, bs), 10.60 (1H, bs); [M+1] 400.2 (C20H22CIN5O2 requires 399.87)

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; PHARMESTE S.R.L.; NAPOLETANO, Mauro; TREVISANI, Marcello; PAVANI, Maria Giovanna; FRUTTAROLO, Francesca; WO2011/120604; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 123470-47-3, name is 5,6-Difluoro-1H-benzo[d]imidazole-2(3H)-thione, 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 123470-47-3, Safety of 5,6-Difluoro-1H-benzo[d]imidazole-2(3H)-thione

1-Formyl-4-(2-hydroxyethyl)piperazine (1.11 g, 7.0 mmol), 5,6-difluoro-2-mercaptobenzimidazole (1.30 g, 7.0 mmol), and diisopropylethylamine (3.62 g, 28.0 mmol) were dissolved in propionitrile (50 mL), and cyanomethyltrimethylphosphonium iodide (6.80 g, 28.0 mmol) was added thereto, followed by stirring for one hour at 92 C. under argon. The reaction mixture was allowed to cool and then poured in water (100 mL), followed by extraction with chloroform (100 mL*3). The organic layer was washed with saturated brine and then dried over sodium sulfate anhydrate, and the product was concentrated under reduced pressure. The crude product was crystallized from acetone-ether, to thereby yield 1-[2-(5,6-difluorobenzimidazol-2-ylthio)ethyl]-4-formylpiperazine (1.78 g, yield 78%) as a yellow crystalline powder. mp: 197.0-198.0 C. IR (KBr) cm-1: 3441, 2825, 1648, 1476, 1431, 1363. 1H-NMR (DMSO-d6): delta2.38 (2H, t, J=5.1 Hz), 2.44 (2H, t, J=5.0 Hz), 2.69 (2H, t, J=7.0 Hz), 3.23-3.38 (4H, m), 3.41 (2H, t, J=7.0 Hz), 7,38-7.58 (2H, m), 7.97 (1H, s), 12.8 (1H s). MS (m/z): 326 (M+), 140 (100).

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, 5,6-Difluoro-1H-benzo[d]imidazole-2(3H)-thione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kowa Co., Ltd.; US2005/20606; (2005); 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. 26832-08-6, name is 1H-Imidazole-4-carboxamide, A new synthetic method of this compound is introduced below., Product Details of 26832-08-6

A suspension of imidazole-4-carboxamide (313 mg) in DMF (3.8 ml) was treated with sodium hydride (60% in mineral oil, 129 mg) at ice-bath temperature and the mixture was stirred at room temperature for 20 min. A solution of 2-[(3S,4S)-4-benzyloxy-3-methanesulfonyloxypentyl]thioanisole (0.92 g) in DMF (7.5 ml) was added and the mixture was stirred at 85 C. for 3 days. The mixture was poured into water and extracted with ethyl acetate. The extract was washed with water, dried and concentrated in vacuo. Column chromatography (dichloromethane:methanol 30:1) gave 1-[(2S,3R)-2-benzyloxy-5-(2-(methylthio)phenyl)-3-pentyl]imidazole-4-carboxamide (1) (96.4 mg, 11.6%) as a pale yellow oil. NMR (CDCl3, d): 1.07 (3H, d, J=6 Hz), 2.0-2.4 (2H, m), 2.44(3H,s) 2.5-2.7(2H, m), 3.6-3.8(1H, m),3.9-4.1(1H, m), 4.39(1H, d, J=12 Hz), 4.58 (1H, d, J=12 Hz),5.37 (1H, s),6.9-7.2 (10H, m), 7.50(1H,d,J=1 Hz), 7.69(1H,d,J=1 Hz). MS (APCI, m/z): 410(M+H)+.

The synthetic route of 26832-08-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tsuji, Kiyoshi; Terasaka, Tadashi; Nakamura, Katsuya; US2004/97571; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 103057-10-9, name is 4-(Chloromethyl)-1-trityl-1H-imidazole, 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. Formula: C23H19ClN2

A.1.1.1. triphenyl[[1-(triphenylmethyl)-1H-imidazol-4-yl]methyl]phosphonium chloride 77.7 g (296 mmol) of triphenylphosphine are added to 670 ml of a solution of 105.5 g (294 mmol) of 4-(chloromethyl)-1-(triphenylmethyl)-1H-imidazole in dimethylformamide. The mixture is heated at 80 C. for 3 hours. The solvent is evaporated and the crude product is taken up in ether and triturated. The precipitate is filtered and dried under vacuum over phosphorus pentoxide. 162 g of product are obtained in the form of yellowish crystals. Melting point=210 C. Yield=89%

The synthetic route of 4-(Chloromethyl)-1-trityl-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Synthelabo; US5552410; (1996); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 51605-32-4, name is Ethyl 5-methyl-1H-imidazole-4-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. COA of Formula: C7H10N2O2

A. N-(2-Fluorophenyl)-5-methyl-1H-imidazole-4-carboxamide To ethyl-4-methyl-5-imidazolecarboxylate (5 g, 32.4 mmol) was added 20 mL of 2-fluoroaniline and potassium carbonate (8.9 g, 64.8 mmol). The reaction mixture was heated to reflux for 18 h then cooled to room temperature and concentrated in vacuo. Water and hexane were added and the precipitate filtered to give the crude product.

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

Reference:
Patent; Bristol-Myers Squibb Co.; US6235740; (2001); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 219814-29-6, These common heterocyclic compound, 219814-29-6, name is 2,5-Dibromo-4-methylimidazole, 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.

[Example 6]; While a mixture of 23.9 g (100.0 mmol) of 2,4-dibromo-5-methylimidazole, 29.4 g (300.0 mmol) of cyclohexanone, and 23.9 g (259.4 mmol) of toluene was stirred at ordinary temperature, 22.5 g (150.0 mmol) of sodium iodide was added thereto to prepare a reaction liquid. After the reaction liquid was stirred at 105C for 12 hours under a nitrogen stream, the liquid was stirred under ice cooling for 1 hour. When 2-bromo-4-methylimidazole in the reaction liquid was analyzed by means of HPLC, it was confirmed that the product was formed in an amount of 13.7 g (82.3 mmol, conversion: 85.3%). After the reaction liquid was concentrated under reduced pressure, the product was purified by silica gel chromatography (ethyl acetate/hexane system) and, after volatile matter was further vaporized to solidify the product, crystals of 2-bromo-4-methylimidazole were obtained in an amount of 12.6 g (yield: 78.1%) as a residue. Incidentally, the NMR spectrum of the crystals was measured and was compared with the NMR spectrum of its specimen, whereby it was confirmed that the product is 2-bromo-4-methylimidazole.

Statistics shows that 2,5-Dibromo-4-methylimidazole is playing an increasingly important role. we look forward to future research findings about 219814-29-6.

Reference:
Patent; SHIKOKU CHEMICALS CORPORATION; EP2141151; (2010); 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. 89830-98-8, name is 5-Cyclopropyl-1H-imidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 5-Cyclopropyl-1H-imidazole

[0415] Into a 20-mL microwave tube was added Example 55a (300 mg, 1.339 mmol), Example 55b (173 mg, 1,61 mmol), Cul (100 mg, 0.53mmol), K3P04 (567 mg, 2.68 mmol) and Nu’,Nu2- dimethylcyclohexane-l,2-diamine (75 mg, 0.53mmol) successively. DMF (6 mL) was added by syringe. The mixture was degassed by nitrogen for three times and sealed. The reaction was heated up to 150C by microwave for lh. LC-MS showed reaction completed. The reaction was filtered, washed by MeOH and purified by flash chromatography to afford Example 55c (110 mg, yield: 32.6%, crude) as a yellow solid. LCMS [M+l]+ = 252.0

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; FRONTHERA U.S. PHARMACEUTICALS LLC; JIN, Bohan; DONG, Qing; HUNG, Gene; (227 pag.)WO2018/151830; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem