Category: imidazoles-derivatives

Adding a certain compound to certain chemical reactions, such as: 693-98-1, name is 2-Methyl-1H-imidazole, 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 693-98-1, HPLC of Formula: C4H6N2

General procedure: Aryl halide (1.0mmol), amine (1.5?2.0mmol), PNP-SSS (0.6molpercent; 0.023g), K2CO3 (2mmol), and DMF (3.0mL) was placed in a 25mL flask equipped with a magnetic stirring bar and heated at 120°C under nitrogen gas. The reaction was then monitored by TLC until the consumption of aryl halide was detected. After completion of the reaction 5mL of water and 5mL of ethyl acetate were added to the reaction mixture. The organic solution was extracted and dried over anhydrous Na2SO4. After removing of organic solvent the crude product was obtained. For further purification the chromatography technique was used.

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

Reference:
Article; Panahi, Farhad; Daneshgar, Fatemeh; Haghighi, Fatemeh; Khalafi-Nezhad, Ali; Journal of Organometallic Chemistry; vol. 851; (2017); p. 210 – 217;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 615-16-7, These common heterocyclic compound, 615-16-7, name is 2-Hydroxybenzimidazole, 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.

To a solution of benzimidazole-2-one (Aldrich, 1.1 g, 7.5 mmol) in DMF (20 ml) was added 3,6-dichlorobenzoisoxazole (1.5 g, 7.5 mmol) and Cs2CO3 (4.8 g, 15 mmol). The suspension was heated to 15O0C in an oil bath and stirred overnight. The mixture was then cooled to room temperature, diluted with water (30 ml) and stirred in a ice bath for 2 hours. The mixture was then filtered. The solid was washed with water and dried under high vacuum to obtain 2.0 g (93%) of a yellow solid as l-(6-chlorobenzisoxazol-3-yl)benzimidazole-2-one. To a solution of the above product (1.0 g, 3.5 mmol) in DMF (15 ml) was added NaOMe solution in methanol (30% wt/wt, 10 ml). The mixture was heated to 8O0C under vacuum to remove residual methanol and then stirred at 11O0C under nitrogen overnight. The mixture was then cooled to room temperature, diluted with water (50 ml), adjusted to pH 6 with 10% aqueous HCl. The resulting suspension was stirred in an ice bath for 2 hours and filtered. The solid was washed with water and dried in an oven (900C) for 2 hours and then under high vacuum at room temperature for 3 hours to obtain a slightly yellow solid. LC-MS m/e: (M+ 1) = 282

Statistics shows that 2-Hydroxybenzimidazole is playing an increasingly important role. we look forward to future research findings about 615-16-7.

Reference:
Patent; MERCK & CO., INC.; WO2006/22954; (2006); A2;,
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. 116343-89-6, name is Methyl 1-phenyl-1H-imidazole-4-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Methyl 1-phenyl-1H-imidazole-4-carboxylate

Step 3 Synthesis of 1-Phenyl-1H-imidazole-4-carboxylic acid To a stirred solution of 1-phenyl-1H-imidazole-4-carboxylic acid methyl ester (200 mg, 0.98 mmol) in a mixture of THF (3 mL), MeOH (3 mL), H2O (2 mL) was added, LiOH.H2O (249 mg, 5.9 mmol) and stirring was continued at ambient temperature for 2 hr. The reaction mixture was concentrated under reduced pressure. Cold water was then added to the residue which was then acidified with 10% aqueous HCl. The product was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure to afford 105 mg (56%) of 1-phenyl-1H-imidazole-4-carboxylic acid.

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 116343-89-6.

Reference:
Patent; Bischoff, Alexander; Subramanya, Hosahalli; Sundaresan, Kumar; Sammeta, Srinivasa Raju; Vaka, Anil Kumar; US2010/160323; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 78581-99-4, 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. 78581-99-4, name is 5,6-Difluorobenzimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of (lR,3S,5S,6r)-6-(((S)-l,l-dimethylethylsulfinamido)methyl) bicyclo[3.1.0]hexan-3-yl methanesulfonate (1.42 g, 4.59 mmol) in THF (15.30 mL) was added cesium carbonate (4.49 g, 13.77 mmol) and 5,6-difluoro-lH-benzo[d]imidazole (0.849 g, 5.51 mmol) and the resulting mixture was stirred at 85C for 16 h. The reaction was cooled to RT, concentrated, diluted with water and extracted twice with EtOAc. The organics were washed with brine, combined, dried over MgS04, concentrated and purified by flash chromatography (5 to 40% of 80:20:2 EA:EtOH:NH40H in hexanes) to give (S)-N- (((lR,3R,5S,6r)-3-(5,6-difluoro-lH-benzo[d]imidazol-l-yl)bicyclo[3.1.0]hexan-6-yl)methyl)- 2-methylpropane-2-sulfinamide (1.03 g, 2.80 mmol, 61.1 % yield) as a white solid. MS (ES+) C18H23F2N3OS requires: 367, found: 368 [M+H]+.

The synthetic route of 5,6-Difluorobenzimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TESARO, INC.; LEWIS, Richard, T.; HAMILTON, Matthew; JONES, Philip; PETROCCHI, Alessia; REYNA, Naphtali; CROSS, Jason; HAN, Michele; SOTH, Michael; MCAFOOS, Timothy; TREMBLAY, Martin; (356 pag.)WO2018/136437; (2018); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 583-39-1, 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 583-39-1 as follows.

Sodium hydroxide (1.60 g, 40 mmol) was dissolved in 2-PrOH (70 ml), benzimidazole-2-thione 1 (6.00 g, 40 mmol) was added followed by portionwise addition of chloroacetamide (3.75 g, 40 mmol). The reaction mixture was refluxed for 3 h, cooled, the precipitate was filtered off, washed with water, and dried. Yield 6.75 g (81%), colorless crystals

According to the analysis of related databases, 583-39-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Bespalov; Gorchakova; Ivanov; Kuznetsov; Kuznetsova; Pankova; Prokopenko; Avdontceva; Chemistry of Heterocyclic Compounds; vol. 50; 11; (2015); p. 1547 – 1558;,
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. 28890-99-5, name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 28890-99-5

A.) 20.0 g (87.3 mmol) 3-bromo-benzonitrile, 16.6 g (80.0 mmol) 6H-benzimidazolo[1 ,2- a]benzimidazole, 67.9 g (320 mmol) potassium phosphate tribasic, 1.5 g (7.88 mmol) cupper(l) iodide and 100 g (875 mmol) DACH ((±)-trans-1 ,2-diaminocyclohexane) in 240 ml dioxane are stirred at 100 C under nitrogen for 7 h. The reaction mixture is filtered hot and the solids are washed with dioxane. The reaction mixture is cooled to 50 C and the crystalized product is filtered of and is washed with methanol. Yield 1 1 .2 g (46 %) 1H-NMR (300 MHz, CDCI3): delta 7.33-7.49 (m, 4H), 7.59 – 7.63 (d, 1 H), 7.72-7.83 (m, 3H), 7.86- 7.90 (d, 2H), 8.22-8.26 (m, 2H),

The synthetic route of 28890-99-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IDEMITSU KOSAN CO., LTD.; RAIMANN, Thomas; SCHAeFER, Thomas; SAITO, Masatoshi; WOLLEB, Heinz; BENEDITO, Flavio Luiz; NISHIMAE, Yuichi; NAKANO, Yuki; NAGASHIMA, Hideaki; (111 pag.)WO2016/157113; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 75370-65-9, 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. 75370-65-9, name is 4-Amino-1H-benzo[d]imidazol-2(3H)-one belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Commercially available (6-chloropyridin-3-yl)methanamine (1 g, 7 mmol) was dissolved in 40 ml of AcOEt and at OC triphosgene (1.93 g,7 mmol) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 10ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10ml) of compound la (1 g, 6.7 mmol) and the mixture was warmed at 80C for8 hours. (TLC AcOEt 9.5 / MeOH 0.5). 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 450 mg of a pale yellow solid. Yield = 21% ‘HNMR (DMSO, 200 MHz) delta 4.32 (2H, d, J = 5.8 Hz), 6.62 (1H, d, J = 7.2 Hz), 6.85 (3H, m), 7.48 (1H, d, J = 8.4 Hz), 7.81 (1H, dd, J = 8.2 Hz, J’ = 2.4 Hz), 8.33 (2H, m), 10.02 (1H, bs), 10.60 (1H, bs); [M+1] 317.8 (C14H12ClN5O2 requires 317.73).

The synthetic route of 4-Amino-1H-benzo[d]imidazol-2(3H)-one has been constantly updated, and we look forward to future research findings.

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

Reference of 39513-26-3,Some common heterocyclic compound, 39513-26-3, name is 5-Bromo-1,3-dihydrobenzoimidazol-2-one, molecular formula is C7H5BrN2O, 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.

To a stirred solution of 5-bromo-1H-benzo[d]imidazol-2(3H)-one (1.0 g,4.69 mmol)inTHF (10 mL)at 0 oc was added NaH (469 mg,11.74 mmol,60%)and the mixture was stirred10 for 30 min. Methyliodide (0.88 mL,14.08 mmol)was added dropwise and the mixture stirred atroom temperature for an additional 16 h. The mixture was quenched with saturated NH4Cl (20mL)and extracted with EtOAc (20 mL x 2). The combined organic layers were dried overanhydrous Na2S04,filtered and concentrated in vacuo. The crude residue was purified by silicagel chromatography (petroleum ether I EtOAc = 5: 1)to give the title compound (630 mg,56%)15 as a white solid. 1HNMR (400 MHz,CDCl3)8 7.23 (d,J= 8.4 Hz,1H),7.12 (d,J= 2.0 Hz,1H),6.84 (d,J= 8.4 Hz,1H),3.41 (s,6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-1,3-dihydrobenzoimidazol-2-one, its application will become more common.

Reference:
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; CYR, Patrick; BRONNER, Sarah; ROMERO, F. Anthony; MAGNUSON, Steven; TSUI, Vickie Hsiao-Wei; WAI, John; LAI, Kwong Wah; WANG, Fei; (251 pag.)WO2017/205536; (2017); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 137049-00-4, A common heterocyclic compound, 137049-00-4, name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, molecular formula is C4H5ClN2O2S, 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.

To a precooled (0 C) solution of intermediate 2.55 (20. mg, 0.078 mmol) in dichloromethane (0.5 mL) was added triethylamine (30 muL, 0.2 mmol) and 1-methyl-1H- imidazole-4-sulfonyl chloride (21 mg, 0.12 mmol). The resulting mixture was allowed to warm to room temperature and stirred for 15 h, then diluted with wet DMSO (0.5 mL), filtered through Celite and purified via mass-directed isolation using ultra-performance liquid chromatography (14 mg, 45% yield).1H NMR (500 MHz, Acetonitrile-d3) d 7.63 (d, J = 1.4 Hz, 1H), 7.56 (d, J = 1.4 Hz, 1H), 7.51 (t, J = 8.6 Hz, 1H), 7.11 (dd, J = 9.9, 2.6 Hz, 1H), 7.01- 6.95 (m, 1H), 3.75- 3.72 (m, 1H), 3.71 (s, 3H), 3.40 (dd, J = 12.3, 5.1 Hz, 1H), 3.10 (dd, J = 12.1, 9.1 Hz, 1H), 2.92 (tt, J = 9.0, 4.0 Hz, 1H), 2.81 (ddd, J = 12.9, 9.6, 3.4 Hz, 1H), 2.05- 1.97 (m, 1H), 1.87- 1.78 (m, 1H), 1.70- 1.56 (m, 2H); AMM 402.0697 (ESI) m/z [calc for C16H18ClFN3O4S (M+H)+ 402.0691].

The synthetic route of 137049-00-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE TRUSTEES OF THE UNIVERSITY OF PENNSYLVANIA; VAL-CHUM, LIMITED PARTNERSHIP; GRENIER, Melissa Carey; SMITH, Amos B., III; FINZI, Andres; DING, Shilei; CHAPLEAU, Jean-Philippe; (240 pag.)WO2020/28482; (2020); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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 3034-50-2 as follows. Application In Synthesis of Imidazole-4-carbaldehyde

Example 63; (3H-Imidazol-4-ylmethyl)-(2-methoxy-phenyl)-amine; To a solution of 2-methoxyaniline (0.62 g, 5 mmol) in methanol (5 ml) was added 4- formylimidazole (0.48 g, 5 mmol). After stirring the mixture overnight at 600C the solution was cooled and sodium borohydride (0.28 g, 7.5 mmol) were added. The reaction mixture was stirred at room temperature for 4 hours. Then water was added and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with water, dried over magnesium sulfate and evaporated. The residue was purified by recrystallisation from heptane/ethyl acetate to yield off-white crystals (0.85 mg, 84%); MS (ISP): 204.3 ((M+H)+’).

According to the analysis of related databases, 3034-50-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2008/46757; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem