Month: March 2021

Adding a certain compound to certain chemical reactions, such as: 26576-46-5, name is 5-Acetoacetlamino benzimdazolone, 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 26576-46-5, Formula: C11H9N3O3

Into a 250 mL round bottom flask is charged anthranilic acid (6.0 g, available from Sigma-Aldrich, Milwaukee, Wis.), deionized water (80 mL) and 5M HCl aqueous solution (20 mL). The mixture is stirred at room temperature until all solids are dissolved, then cooled to 0 C. A solution of sodium nitrite (3.2 g) is dissolved in deionized water (8 mL) and then is added dropwise into the solution of anthranilic acid at a rate that maintains the internal temperature range in the mixture of 0-5 C. Once diazotization is complete, the solution is stirred an additional 0.5 hr. Prior to coupling reaction, any excess nitrite ion is destroyed using aliquots of dilute aqueous urea solution. A second mixture for the coupling component is prepared by charging deionized water (100 mL) and sodium hydroxide (5.5 g) into a 500-mL vessel, stirring to dissolution, then adding 5-(acetoacetamido)-2-benzimidazolone (10.5 g, available from TCI America, Portland, Oreg.) into this solution while vigorously stirring until all solids dissolved. A separate solution containing glacial acetic acid (15 mL), 5M NaOH solution (30 mL) and deionized water (200 mL) is then added dropwise into the alkaline solution of coupling component while stirring vigorously, after which the coupling component is precipitated as a white suspension of particles, and the mixture is weakly acidic. For coupling reaction, the chilled diazotization mixture is slowly added dropwise into the suspension of coupling component, while stirring vigorously, to produce a reddish-yellow slurry of pigment. The slurry is stirred at room temperature for another 2 hours, after which time the pigment is isolated by vacuum-filtration, is washed with several volumes of deionized water (3 portions of 250 mL), then freeze-dried. Reddish-yellow granules of pigment are obtained, and TEM images show large aggregates of rod-shaped particles having high aspect ratio, with particle diameters ranging from 200 to 500 mm.

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; Xerox Corporation; US7503973; (2009); B1;,
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. 2849-93-6, name is 1H-Benzimidazole-2-carboxylic acid, A new synthetic method of this compound is introduced below., category: imidazoles-derivatives

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.

The synthetic route of 2849-93-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sun Yat-sen University; Qiu Liqin; Jiang Xiaoding; (74 pag.)CN109336887; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 22884-10-2,Some common heterocyclic compound, 22884-10-2, name is 2-(1H-Imidazol-1-yl)acetic acid, molecular formula is C5H6N2O2, 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 of (3- { [(ethylimino)methylidene] amino } propyl)dimethylamine hydrochloride (EDC.HC1) (1.2 mmol), 1-hydroxybenzotriazole (HOBt) (1.2 mmol), N,N-diisopropylethylamine (0.35 ml, 2 mmol), 2-(1H-imidazol-1-yl)acetic acid (1.2 mmol), and 3-methyl-4-phenylaniline (1 mmol) in dimethylformamide (7 mL) was stirred for 36 hours at room temperature. Then the reaction mixture was treated withwater (35 mL), the crude product was filtered and purified by recrystallization from acetonitrile. Yield: 40%.The spectral data for Compound 30 is listed below: Compound 30:?HNMR(DMSO-d6): 5= 10.55 (s, 1H,NI]), 7.65 (s, 1H, CmidH), 7.45 (m, 4H, Cp,J]), 7.37 (m, 3H, CFhH) ,7. 17 (m, 2H, CFhH, CmiciH), 6.9 (d, 1H, CmiciH), 4.9 (s, 2H, CH2), 2.2 (s, 3H, CH3) ppm.LS-MS (m/z): calcd./found for [M+H] 292.16. 1/292.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(1H-Imidazol-1-yl)acetic acid, its application will become more common.

Reference:
Patent; MAYO FOUNDATION FOR MEDICAL EDUCATION AND RESEARCH; SPRINGER, Wolfdieter; FIESEL, Fabienne C.; CAULFIELD, Thomas R.; (172 pag.)WO2018/23029; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 23814-14-4, name is 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylic acid, molecular formula is C8H6N2O3, 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: C8H6N2O3

To a stirred solution of 2-oxo-2,3-dihydro-lH-benzo[d]imidazole-5-carboxylic acid56 150 mg) and methyl indoline-4-carboxylate114 (149 mg) in methanol (5 ml) was added 4-(4,6- dimethoxy-l,3,5-triazin-2-yl)-4-methylmorpholin-4-ium chloride 115 (280 mg, DMTMM). The reaction muxture was stirred for 4 h at room temperature. LC/MS analysis indicated that the reaction was complete. The reaction mixture was concentrated in vacuo and the residue was purified by preparative reverse-phase HPLC (Gemini NX CI 8, 12 nm, 5mu, 100 x 30 mm, flow rate 40 ml/min, eluant: CH3CN/H2O containing formic acid) followed by lyophilisation in vacuo to afford methyl l-(2-oxo-2,3-dihydro-lH-benzo[d]imidazole-5-carbonyl)indoline-4-carboxylate (60 mg, 21%) as a white solid. MS (ISP): 338.1 ([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 23814-14-4, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; GOERGLER, Annick; NORCROSS, Roger; DEY, Fabian; KUSZNIR, Eric Andre; (206 pag.)WO2019/43217; (2019); 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. 17289-25-7, name is (1-Methyl-1H-imidazol-4-yl)methanol, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C5H8N2O

To a solution of intermediate 111 (400mg, 1. [02MMOL)] in DMF [(20ML)] was added portionwise sodium hydride (60percent in mineral oil, 101mg, 2. [55MMOL)] and the mixture was stirred at room temperature for 20 minutes. Intermediate 22 (173mg, 1. [32MMOL)] was then added and the mixture was heated at [60¡ãC] for 3 days and then poured into water. After extraction with [CH2CI2,] the organic phase was dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by chromatography on silica gel eluting with [CH2CI2/MEOH] (90: 10). After trituration with diisopropyl oxide, the title compound was obtained as a yellow solid (130mg, 26percent); m. p. [217¡ãC] ; TOF MS ES + exact mass calculated for [C3OH26N6O] : 487.2246 (MH+). Found: [487. 2247] (MH+).

According to the analysis of related databases, 17289-25-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2004/13135; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 583-39-1, name is 2-Mercaptobenzimidazole, 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: C7H6N2S

General procedure: A mixture of 0.001 mol of chloroethynylphosphonate1a-1c and 0.002 mol of benzimidazole-2-thione 2d in 15 mL of anhydrous acetonitrile was stirred at room temperature for 2-5 h. The precipitate was filtered off. The solvent was removed from the filtrate, the precipitate was combined and recrystallizedfrom ethanol. Yields and melting points of the obtained compounds are given in Table 1.

The synthetic route of 2-Mercaptobenzimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Egorov; Piterskaya, Yu. L.; Kartsev; Polukeev; Krivchun; Dogadina; Russian Journal of General Chemistry; vol. 88; 9; (2018); p. 1824 – 1831; Zh. Obshch. Khim.; vol. 88; 9; (2018); p. 1478 – 1485,8;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, 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. Formula: C4H6N2S

Dithiafulvalenyl compound 1 (0.2 mmol), mercapto-thiazole 2 (2 mmol, 10 equiv.), and I2 (0.6 mmol, 3 equiv., 152.4 mg) were dissolved in DMSO (3 mL). The reaction mixture was stirred at 25 C for 12 h under N2 atomsphere. Then quenched with a saturated solution of Na2S2O3 and stirred for half an hour, the solution was extracted with dichloromethane (CH2Cl2). The organic layer was separated, and dried over Na2SO4. Then the organic solvent was removed in vacuo to afford the respective thiadiazole-based dithiafulvalene (DTF) derivatives (3), which were purified by column chromatography (silica gel, PE / CH2Cl2) to afford pure substances.

The synthetic route of 60-56-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Fu, Huimin; Zhao, Bangtun; Zhu, Weimin; Tetrahedron Letters; vol. 60; 2; (2019); p. 124 – 128;,
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

Preparation of 1-(4-chloro-2-(3-hydroxypyrrolidin-1-yl)benzyl)-3-(2,3-dihydro-2-oxo-1H-benzo[d]imidazol-4-yl)urea 1-(2-(aminomethyl)-5-chlorophenyl)pyrrolidin-3-ol 2ai (1.18 g, 5.2 mmol) was dissolved in 40 ml of AcOEt and at 0C triphosgene (1.4 g, 5.2 mmol) 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 1a (674 mg, 4.52 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt 8 / MeOH 2). The solvent was evaporated and the crude was dissolved in AcOEt (80 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 390mg of a pale pink solid. Yield = 21% 1HNMR (DMSO, 200 MHz) delta 2.20 (2H, m), 3.33 (4H, m), 3.69 (2H, s), 4.29 (1H, b), 5.20 (1H, b), 6.62 (2H, m), 6.90 (4H, m), 7.27 (1H, d, J = 8 Hz), 8.29 (1H, s), 9.95 (1H, bs), 10.60 (1H, bs); [M+1] 402.4 (C19H20ClN5O3 requires 401.85).

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.; EP2377850; (2011); 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. 143722-29-6, name is 1-(4-Bromobenzyl)-2-butyl-4-chloro-1H-imidazole-5-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C15H16BrClN2O

EXAMPLE 15 2-n-Butyl-4-chloro-1-[(2′-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1′-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol A mixture of the oil obtained in Example 14 (0.05 m=17.8 g), 2-(2′-triphenylmethyl-2’H-tetrazol-5′-yl)phenylboronic acid (0.065 m=29.3 g), potassium carbonate (0.1 m=13.8 g), water 11 mL), tetra-n-butylammonium bromide (0.005 m=1.61 g), triphenylphosphine (0.006 m=1.58 g) in 200 mL toluene was evacuated and released to nitrogen three times and maintained under a nitrogen atmosphere. Tris(dibenzylideneacetone)dipalladium (1.5 mm=0.64 g) was charged and the reaction was heated at 75 to 81 C. for 12 hours. The cooled reaction mixture was filtered to remove some grey solid. The toluene layer was stirred with sodium borohydride (0.1 m=3.8 g), tetra-n-butyl ammonium bromide (0.005 m=1.6 g), and 30 mL water for six hours. The mixture was filtered through a Celite cake to remove the black tarry precipitate. The organic layer was washed once with 100 mL water then stirred with a solution of thiourea (7 g) in 100 mL water for 1 hour. Some brown sludge (palladium complex) was formed and precipitated out. The mixture was filtered and the organic layer was separated then treated with a fresh solution of thiourea (7 g) in 100 mL water for 1 hour. The organic layer was separated, washed once with 100 mL water and once with 100 mL saturated sodium chloride solution. The organic layer was stirred with 30 g magnesium sulfate and 15 g charcoal for 1 hour. The solid was removed by filtering through a Celite cake. The filtrate was concentrated to an oil and crystallized from 35 mL of isobutyl acetate in an ice bath. The solid was collected and dried under a stream of nitrogen to a constant weight of 17.17 g.

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 143722-29-6.

Reference:
Patent; E. I. Du Pont de Nemours and Company; Merck & Co., Inc.; US5310928; (1994); A;,
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. 7152-24-1, name is 2-(Methylthio)benzimidazole, This compound has unique chemical properties. The synthetic route is as follows., Safety of 2-(Methylthio)benzimidazole

To a stirred solution of a benzimidazole g (beta.OOmmols) and p- fluoronitrobenzene h (6.00mmols) in 1OmL of anhydrous DMF, was added [potassium t-butoxide (f-BuOK) (7.61 mmols, 1.25eq.), and the reaction mixture was stirred at 80 0C overnight. The reaction mixture was added into 5OmL of water and the product was extracted with ethylacetate (3 x 2OmL). The extracts were washed with brine and concentrated. Column chromatography on silica gel using mixture of hexane:ethylacetate provided compound i in 25-45% yields.To a stirred solution of compound i (1.31 mmols) in 2OmL of 1 :1 CH2CI2IEtOH, was added SnCb (13.06mmols) followed by a few drops of water. The mixture was stirred overnight and concentrated. 2OmL of water was added to the residue, and the solution the brought to pH ~ 8-9 using 2N NaOH. The resulting mixture was extracted with ethylacetate (2OmL x 4), washed with brine (2OmL), dried over Na2SO-I, and concentrated to afforded compound j in 70-97% yields.To a solution of compound j (0.30mmols) in 5mL of CH2CI2, was added an acyl chloride k (0.30mmols), followed by diisopropyl-ethylamine (0.60mmols). The resultant mixture was stirred at room temperature for 30min and eluted through a short pad of silica gel using mixture of hexane:ethylacetate to afford, upon concentration, the product I in 80-96% yields.

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 7152-24-1.

Reference:
Patent; SYNTA PHARMACEUTICALS CORP.; WO2007/112093; (2007); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem