Category: imidazoles-derivatives

Reference of 641571-11-1, 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. 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

5-(4-methyl-1H-imidazol-1-yl)-3-(trifluoromethyl)-benzeneamine 110 g (0.45 moles) of formula (XI) was dissolved in 1 L of chloroform. 4-methyl-3-nitro benzoyl chloride of the formula (IIA) prepared above was added slowly to the reaction mass at 10-15 C. for 60 minutes. Reaction mass was raised to room temperature and maintained for 4 hours. Reaction mass was filtered, washed with chloroform and dried.Yield: 161 g (87%) Purity: 99% (by HPLC) [0059] IR and NMR were consistent with the proposed structure.

The synthetic route of 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Natco Pharma Limited; Kompella, Amala; Bhujanga Rao, Adibhatla Kali Satya; Rachakonda, Sreenivas; Gampa, Venugopala Krishna; Nannapaneni, Venkaiah Chowdary; US2013/210847; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 46006-36-4, name is 1H-Benzimidazole-7-carboxylic acid, 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 46006-36-4, Formula: C8H6N2O2

B. (lH-Benzo[d]imidazol-4-yI)methanol.; lH-Benzo[d]imidazole-4- carboxylic acid (1.04 g, 6.41 mmol) was suspended in anhydrous tetrahydrofuran (80 mL) and cooled to -78 0C. A solution of lithium aluminum hydride in tetrahydrofuran (2.0M, 6.4 mL) was added via syringe. The reaction was allowed to warm to room temperature and stirred overnight. The reaction was quenched with methanol and adsorbed onto silica gel. Flash chromatography (20% MeOH in EtOAc) afforded a white solid (550 mg, 3.72 mmol, 58%). MS (ESI) m/z 149.0 [M+l]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-Benzimidazole-7-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; WO2008/51494; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 57090-88-7, 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. 57090-88-7 name is 1H-Imidazole-4-carbonitrile, 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.

To a round bottom flask was added 1H-imidazole-4-carbonitrile (300 mg, 3.22 mmol), 2- bromopropane (794 mg, 6.44 mmol), and K2CO3 (890 mg, 6.44 mmol) in DMF (9 ml). The reactiom mixture was stirred at room temperature for 18 h. The reaction mixture was filtered. The solvent was concentrated in vacuo. The residue was purified by prepHPLC to afford 310 mg of 1-Isopropyl-lH-imidazole-4-carbonitrile TFA salt and 71 mg of 3- isopropyl-3H-imidazole-4-carbonitrile TFA salt region-isomer.1-Isopropyl-lH-irnidazole-4-carboriitrile TFA salt was dissolved in EtOAc, washed with sat. NaHCO3, brine, dried under anhy. Na2SO4, filtered and concentrated to afford 200 mg of 1-isopropyl-l/Mrnidazole-4-carbonitrile as a colorless oil, m/z 136.5 [M+l]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-Imidazole-4-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2009/70485; (2009); 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 934-32-7 as follows. Recommanded Product: 1H-Benzo[d]imidazol-2-amine

General procedure: A mixture of ethyl acetoacetate and/or acetylacetone (1 mmol) or malononitrile(1.1 mmol), 2-aminobenzimidazole (1 mmol), aldehyde (1 mmol) and [PVPH]ClO (30 mg, 6.84 mol %) was heated at 100 C in an oil bath for the appropriate time.After completion of the reaction [monitored by thin layer chromatography (TLC): nhexane:ethyl acetate (3:1)], the reaction mixture was cooled to room temperatureand EtOH (5 mL) was added to it and filtered to separate the catalyst. Afterevaporation of the solvent from the filtrate, the crude solid product wasrecrystallized from ethanol to obtain pure A or B products.The spectral [IR, proton ( 1H) NMR and 13C NMR] data of new compounds arepresented below.

According to the analysis of related databases, 934-32-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Abedini, Masoumeh; Shirini, Farhad; Mousapour, Maryam; Goli Jolodar, Omid; Research on Chemical Intermediates; vol. 42; 7; (2016); p. 6221 – 6229;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 3034-38-6,Some common heterocyclic compound, 3034-38-6, name is 5-Nitro-1H-imidazole, molecular formula is C3H3N3O2, 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 HNim (0.2 mmol,0.027 g), AgNO3 (0.4 mmol, 0.068 g), ammonia (25%,10.0 mL) was stirred for 30 min in air and then transferred and sealed in a 25-mL Teflon-lined reactor andheated at 120C for 60 h, and then cooled to roomtemperature at a rate of 5C/h. Yellow block crystals of I were obtained in 67% yield based on silver.

The synthetic route of 3034-38-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhou; Lu; Luo; Chen; He; Dong; Russian Journal of Coordination Chemistry; vol. 44; 12; (2018); p. 812 – 817;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 75370-65-9, The chemical industry reduces the impact on the environment during synthesis 75370-65-9, name is 4-Amino-1H-benzo[d]imidazol-2(3H)-one, I believe this compound will play a more active role in future production and life.

To a solution of 3-aminomethyl-6-trifluoromethylpyridine (lg, 4.7 mmol) in THF (30 mL) was added CDI (2.1 mol eq) and the mixture was heated at 70C overnight. The reaction mixture was evaporated, water was added and the aqueous phase was extracted with EtOAc (3×20 mL). The recombined organic phases were anhydrified over Na2SO4 and evaporated at reduced pressure. The oil obtained (0.96g, 3.5 mmol) was dissolved in DMF (20 mL) and the bicyclic amine la was added (0.8 mol eq), then the mixture obtained was heated at 100C overnight. The solvent was removed at reduced pressure and the residue was purified by crystallization from a mixture of MeOH/EtOAc to obtain the product as a pale yellow solid (0.42g, 1.2 mmol, 34% Yield). ‘HNMR (DMSO, 400 MHz) delta 4.43 (bs, 2H), 6.64 (d, 1H, J=6), 6.83 (t, 1H, J=8), 6.96 (d, 2H, J=8), 7.89 (d, 1H), 8.03 (d, 1H), 8.42 (bs, 1H), 8.72 (s, 1H), 10.07 (bs, 1H), 10.59 (bs, 1H). [M+1] 351.80 (C15H12F3N5O2 requires 351.28).

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, 4-Amino-1H-benzo[d]imidazol-2(3H)-one, other downstream synthetic routes, hurry up and to see.

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

Synthetic Route of 930-62-1, These common heterocyclic compound, 930-62-1, name is 2,4-Dimethylimidazole, 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.

A stirred solution of 3-(4-bromophenyl)-1 ,4-diazaspiro[4.4]non-3-en-2-one (D3) (770 mg2,4-dimethyl-1 H-imidazole (379 mg, 3.94 mmol) and copper bis(2,2,6,6-tetramethyl- 3,5-heptanedionate) (337 mg, 0.788 mmol) in DMF (3 ml) at room temperature, under argon was treated with potassium tert-butoxide (1179 mg, 10.51 mmol). After stirring at room temperature for 5 min, the mixture was heated to 12O0C and this temperature was maintained for 16 h. Further batches of the imidazole (379 mg) and copper bis(2, 2,6,6- tetramethyl-3,5-heptanedionate) (337 mg) were added and heating was continued for 7 days. The reaction mixture was cooled and diluted with saturated aqueous sodium bicarbonate solution (100 ml) and ethyl acetate (100 ml). After mixing, the mixture was filtered through Kieselghur. The ethyl acetate layer was separated and the aqueous phase re-extracted with ethyl acetate (50 ml). The combined organics were dried (MgSO4) and evaporated. The residue was applied in MeOH to an SCX column (10 g). After washing with MeOH the product was eluted with 2M NH3-MeOH. Evaporation afforded a brown gum. Chromatography (1 Og isolute column, 0-2% MeOH-DCM) afforded, after solvent removal, material (250 mg) consistent with presence of 2 isomers in approx 9:1 ratio with the major component subsequently confirmed (by 1H NMR nOe studies at the final product stage) as the title compound.Mass Spectrum (Electrospray LC/MS): Found 309 (MH+). Ci8H20N4O requires 308. Ret. time 1.02 min

The synthetic route of 930-62-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/34061; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 583-39-1, 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. 583-39-1, name is 2-Mercaptobenzimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Benzyl chloride or 1-iodopropane, 89.25 mmol, and potassium carbonate, 170.0 mmol, were added to a solution of 85.0 mmol of 1,3-dihydro-2H-benzimidazole-2-thione in 140 mL of acetone. The mixture was refluxed for 3 h with stirring and poured into water with stirring to dissolve inorganic com-ponents. The precipitate was filtered off and washed with water and methanol. Compound 1b was dried and recrystallized from 20 mL of methanol. Compound 1a required no additional purification. Compound 1a. Yield 93%, colorless crystals, mp 180-181C. 1 H NMR spectrum, delta, ppm: 4.56 s (2H, CH 2 ), 7.07 t (2H, H arom , J = 4.0 Hz), 7.21 t (1H, H arom , J = 6.8 Hz), 7.28 t (2H, H arom , J = 7.2 Hz), 7.35-7.45 m (4H, H arom ), 12.04 br.s (1H, NH). Compound 1b. Yield 55%, colorless crystals, mp 151-152C. 1 H NMR spectrum, delta, ppm: 1.07 t (3H, CH 3 , J = 7.2 Hz), 1.80 sext (2H, CH 2 , J = 6.8 Hz), 3.25 t (2H, CH 2 , J = 7.2 Hz), 7.05 s (2H, H arom ), 7.37 s (1H, H arom ), 12.27 s (1H, NH).

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

Reference:
Article; Kharaneko; Russian Journal of Organic Chemistry; vol. 54; 9; (2018); p. 1363 – 1368; Zh. Org. Khim.; vol. 54; 9; (2018); p. 1350 – 1354,5;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 50995-95-4, A common heterocyclic compound, 50995-95-4, name is 2-Propylimidazole, molecular formula is C6H10N2, 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.

In a 1-L round-bottomed flask, 2-propylimidazole (15.0 g, 136 mmol) and I2 (110 g, 435mmol) were suspended in a mixture of CHCl3 (350 mL) and 2 M NaOH aqueous solution (350mL), and the mixture was stirred at room temperature of 45 h. To this mixture, a saturatedNa2S2O3 aqueous solution until the excess amount of I2 was quenched, the mixture was leftstand until the mixture separate to aqueous and CHCl3 layers. The CHCl3 layer was removedby using dropping funnel, then the aqueous layer was neutralized with acetic acid and asaturated NaHCO3 aqueous solution. The resulting precipitate was collected by filtration andwashed with water, then dried in vacuo at 60 C, to give 11 (43.7 g, 85%) as a soft yellowpowder;

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:
Article; Murata, Tsuyoshi; Yamamoto, Yosuke; Yakiyama, Yumi; Nakasuji, Kazuhiro; Morita, Yasushi; Bulletin of the Chemical Society of Japan; vol. 86; 8; (2013); p. 927 – 939;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 760212-58-6, 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. 760212-58-6, name is 1-(4-Bromophenyl)-2-phenyl-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step S101: 2-phenyl-4-N-p-bromophenylbenzimidazole was dissolved in THF (tetrahydrofuran); preferably,In the step, 2-phenyl-4-N-p-bromophenylbenzimidazole was 1. Ommol, THF (tetrahydrofuran)Step S102: cooling to -78 C, adding n-butyllithium, for one hour; preferably, n-butyllithium is 1 · lmmol in this step;Step S103: Diphenylphosphonium chloride is added and the temperature is raised to room temperature for 12 hours. Preferably, diphenylphosphonium chloride is 1.2 mmol in this step;Step S104; adding a methanol quenching reaction while adding 30% H2O2 aqueous solution to give 4- (1-methylbenzimidazolyl) -triphenylphosphine oxide; preferably, 30% H2O2 aqueous solution in this step is 5 ml ; Yield: 70%

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, 1-(4-Bromophenyl)-2-phenyl-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Wuhan Shang Sai Optoelectric Technology Co., Ltd.; Wang Lei; Pan Biao; Wang Bo; Mu Guangyuan; (19 pag.)CN104370964; (2017); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem