Tag: M.W=200-300

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. 870837-18-6, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, A new synthetic method of this compound is introduced below., Quality Control of 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde

Ethyl diethylphosphonoacetate (5.70 g) and lithium hydroxide monohydrate (1.30 g) were sequentially added to a mixed solution of 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (5.00 g) in THF (20 mL) and ethanol (5.0 mL), and the reaction solution was stirred at room temperature for nine hours. A 2 N sodium hydroxide solution (20 mL) was added to the reaction solution, and the reaction solution was stirred at room temperature for 12 hours. The reaction solution was cooled to 0C, and 2 N hydrochloric acid (20 mL) was added to the reaction solution. The resulting precipitate was collected by filtration. The resulting precipitate was washed with water and ethyl acetate to obtain 5.10 g of the title compound. The property values of the compound are as follows. 1H-NMR (DMSO-d6) delta (ppm): 7.81 (s, 1H), 7.60 (d, J = 16 Hz, 1H), 7.56 (s, 1H), 7.39 (d, J = 8.0 Hz, 1H), 7.35 (d, J = 8.0 Hz, 1H), 7.16 (s, 1H), 6.66 (d, J = 16 Hz, 1H), 3.88 (s, 3H), 2.15 (s, 3H).

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; Eisai R&D Management Co., Ltd.; EP2019093; (2009); A1;,
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. 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: imidazoles-derivatives

Example 5; Preparation of ethyl-4-(1-hydroxy-1-methylethyl)-2-propyl-1-{4-[2-(trityl tetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate4-(1-Hydroxy-1-methylethyl)-2-propyl-1H-imidazole-5-carboxylic acid ethyl ester (100 g), N-(triphenylmethyl)-5-(4′-bromomethyl biphenyl-2-yl)tetrazole (250 g), potassium carbonate (170 g) & tetra butyl ammonium bromide (15 g) in acetone (2.5 L) were refluxed for 10-16 hours. Progress of reaction was monitor by HPLC. After completion of reaction, reaction mass was cooled and filtered to remove the salts. Inorganic salts were washed with acetone (300 mL). Acetone from combine the filtrate and washings was distilled. The residue obtained was crystallized in acetonitrile to get ethyl-4-(1-hydroxy-1-methylethyl)-2-propyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate (280 g).HPLC Purity=98.5%

The synthetic route of 144689-93-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ramanjaneyulu, Gorantla Seeta; Mohan, Bandari; Ray, Purna Chandra; Sethi, Madhuresh Kumar; Rawat, Vijendra Singh; Krishna, Yerramalla Raja; Lakshminarayana, Vemula; Srinivas, Mamidi; US2009/281327; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 28890-99-5, name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]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 28890-99-5, COA of Formula: C13H9N3

d) Compound 8-3 (3.0 g, 8.10 mmol), benzimidazolo[1,2-a]benzimidazole (1.85 g, 8.91mmol), and potassium phosphate (1.96 g, 16.2 mmol) were added to NMP (30 mL). Themixture was stirred at 190 C for 17 h. In addition, potassium phosphate (3.92 g, 32.4 mmol) was added there, and the mixture was stirred at the same temperature for 27 h. Af8-2 ter reaction mixture was cooled at room temperature, it was diluted with water to give asolid. The solid was collected by filtration, and it was washed with 300 mL of MeOH. Thecrude product was purified by by column chromatography on silica gel eluting with CH2CI2to yield 4.7 g (78%) of compound (B-29) as a white solid. LC-MS (m/z) 745.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, and friends who are interested can also refer to it.

Reference:
Patent; IDEMITSU KOSAN CO., LTD.; NISHIMAE, Yuichi; KOHLSTEDT, Julia; SCHAeFER, Thomas; NAGASHIMA, Hideaki; (114 pag.)WO2016/97983; (2016); A1;,
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. 67085-11-4, name is 4-(4-Chlorophenyl)-1-(1H-imidazol-1-yl)butan-2-ol belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 67085-11-4

(1) 3 kg of 1-(2-hydroxy-4-(4-chlorophenyl)butyl)-1-hydro-imidazole was dissolved in 30 kg of methylene chloride.3.5 kg of thionyl chloride was added dropwise at a rate of 1.5 ml/s at 20C and slowly warmed to 33C.The reaction was incubated for 1 hour, then refluxed at 60C for 1 hour, and slowly cooled to below 15C to obtain a reaction liquid;(2) In the reaction liquid obtained in step (1), add 10 C. water at a rate of 0.5 ml/s with stirring, and the volume ratio of the reaction liquid to water is 0.005:1, and then 1.0 to 1.5 kg/L. Add anhydrous sodium carbonate, suction filter, discard the solid,The liquid was concentrated at 55[deg.] C. until no dichloromethane was distilled off, dried and obtained.Upon detection, the yield of the product of this example was 99.18%. The target product and impurity levels were determined using HPLC and standards.The target product, 1-(2-chloro-4-(4-chlorophenyl)butyl)-1H-imidazole, was detected to be 99.17%.The content of 1-(1-chloro-4-(4-chlorophenyl)butan-2-yl)-1-hydro-imidazole is 0.53%.The 1-(2-hydroxy-4-(4-chlorophenyl)butyl)-1H-imidazole content was 0.12%.

The synthetic route of 67085-11-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhuzhou Qianjin Pharmaceutical Co., Ltd.; Peng Kaifeng; Zhang Yingshuai; Wen Fengqiu; Li Sanxin; Gong Yun; Li Fujun; (10 pag.)CN105175338; (2018); B;,
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. 40197-20-4, name is 5-Bromo-1H-benzo[d]imidazole-2-carboxylic acid, A new synthetic method of this compound is introduced below., Product Details of 40197-20-4

N-[3-(dimethylamino)propyl]-N?-ethylcarbodiimide hydrochloride (1.2 g) was added to a mixture of 5-bromo-1H-benzimidazol-2-carboxylic acid (1.0 g), 1-[4-(trifluoromethyl)benzyl]piperazine (1.0 g), 1H-benzotriazol-1-ol (840 mg),and N,N-dimethylformamide (10 ml: hereinafter, abbreviated as DMF), followed by stirring at room temperature overnight.A saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, followed by stirring atroom temperature for 1 hour, and the resulting solid was collected by filtration, followed by drying under reduced pressure.The obtained solid was dissolved in a mixture of chloroform (100 ml) and ethanol (1 ml) while heating to reflux. Themixture was cooled to room temperature and then hexane (100 ml) was added thereto. The resulting solid was collectedby filtration, followed by drying under reduced pressure, thereby obtaining (5-bromo-1H-benzimidazol-2-yl){4-[4-(trifluoromethyl)benzyl]piperazin-1-yl}methanone (1.4 g) as a solid.

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; Astellas Pharma Inc.; NAGASHIMA, Takeyuki; TSUJIMOTO, Susumu; (27 pag.)EP3231425; (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. 13275-42-8, name is 2-(2-Bromophenyl)-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C13H9BrN2

General procedure: 2-(2-Bromophenyl)benzimidazole (1 mmol), substituted aldehyde (1.2 mmol), NaN3 (1.8 mmol), Cu (10mol%), L-proline (20 mol%), and Cs2CO3 (1 mmol) were added to DMF in a 50 mL round bottom flask, and then the mixture was refluxed at 80 C for 16 h under nitrogen atmosphere. TLC was monitored the reaction till completed, and then the reaction mixture was cooled to room temperature. The mixture was poured into the dichloromethane, washed with brine and water. The organic layer was concentrated with evaporator, and the residue was purified by column chromatography on silica gel to give the target compound (A-4 to A-37).

According to the analysis of related databases, 13275-42-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Li, Jun-cai; Wang, Ren-xuan; Sun, Yu; Zhu, Jia-kai; Hu, Guan-fang; Wang, Yu-ling; Zhou, Rui; Zhao, Zhong-min; Liu, Ying-qian; Peng, Jing-wen; Yan, Yin-fang; Shang, Xiao-fei; Bioorganic Chemistry; vol. 92; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 870837-18-6, A common heterocyclic compound, 870837-18-6, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, molecular formula is C12H12N2O2, 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 B8 a) A microwave vessel was charged with intermediate 15 (1 g, 4.63 mmol), l-[3- (trifluoromethyl)phenyl] -propane- 1,2-dione (1 g, 4.63 mmol), NH4(OAc) (3.57 g, 46.3 mmol) and AcOH (10 ml). The r.m. was stirred and heated at 160 0C for 7 min. under microwave irradiation. The r.m. was cooled and poured into a sat. aq. Na2Ctheta3 sol. The mixture was extracted with DCM. The o.l. was washed with H2O and dried (MgStheta4). Filtration and concentration under reduced pressure gave the crude product which was purified by flash chromatography over silicagel (eluent, 100: 0 to 90: 10 DCM/MeOH, gradient elution). The product fractions were collected and evaporated. The residue was purified further by preparative SFC (Chiralpak Diacel AD 20 mm, mobile phase:isocratic 80 % CO2, 20 % MeOH with 0.2 % isopropylamine). The product fractions were collected and worked up to yield 463 mg of compound 12 after trituration with DIPE (24 %).

The synthetic route of 870837-18-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ORTHO-MCNEIL-JANSSEN PHARMACEUTICALS, INC; WU, Tongfei; GIJSEN, Henricus, Jacobus, Maria; ROMBOUTS, Frederik, Jan, Rita; BISCHOFF, Francois, Paul; BERTHELOT, Didier, Jean-Claude; OEHLRICH, Daniel; DE CLEYN, Michel, Anna, Jozef; PIETERS, Serge, Maria, Aloysius; MINNE, Garrett, Berlond; VELTER, Adriana, Ingrid; VAN BRANDT, Sven, Franciscus, Anna; SURKYN, Michel; WO2011/6903; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 28890-99-5, 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.

(3-bromophenyl)(9,9-dimethyl-9H-xanthen-4-yl)diphenylsilane (2, 300 mg, 0.55 mmol), 5H-benzo [d]benzo[4,5]imidazo[1,2-a]imidazole (3, 125 mg, 0.603 mg),cBRIDP (19.3 mg. 0.055 mmol) and tBuONa (132 mg, 1.37mmol) were dissolved in xylene (5 mL). The mixture wasdegassed by bubbling nitrogen through for 15 min. Alkylpalladiumchloride dimer (6 mg, 0.016 mmol) was added,and the mixture was again degassed by bubbling nitrogenthrough for another 15 min before being heated to 120 C.for 2 h. The reaction was quenched with water. The organicphase was separated and the aqueous phase was extractedwith dichloromethane. The combined organics was dried onMgS04 , filtered, and concentrated in vacuo. The crudeproduct was purified using reverse phase chromatography(20:80 to 70:30 THF:water, 1CV, 70:30 to 100:0 THF:water,10 CV, then THF). The crude product was then re-purifiedusing reverse phase chromatography (20:80 to 40:60 THF:water, 1 CV, 40:60 to 70:30 THF:water, 10 CV, then 70:30THF:water). The product was purified using normal phaseflash colunm chromatography (silica, 1:99 to 100:0 dichloromethane:heptane ). It was retained on the silica before 1:1THF:dichloromethane was used. This material was purifiedagain by normal phase chromatography (silica, 50:50 to100:0 dichloromethane:heptane) to afford Compound A aswhite solid.

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, 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Universal Display Corporation; Wolohan, Peter; Feldman, Jerald; (128 pag.)US2018/287079; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

3584-66-5, name is 5-Chloro-2-(trichloromethyl)-1H-benzo[d]imidazole, 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: C8H4Cl4N2

To a suspension [OF 5-CHLORO-2-TRICHLOROMETHYL-1H-BENZOIMIDAZOLE] (100 mg, 0.37 mmol) in acetonitrile (4 mL) was added N-methylpiperazine (0.04 mL, 0.4 [MMOL).] The mixture was stirred for 10 min then ammonium acetate (29 mg, 0.38 [MMOL)] was added. After 18 h the reaction mixture was diluted with satd aq [NAHCO3] (10 mL), and then extracted with [DICHLOROMETHANE] [(3 X 10] mL). The combined extracts were dried [(NA2SO4)] and then concentrated under reduced pressure. The crude product was purified on silica gel (10 g; 0-10% methanol (2 M NH3)/dichloromethane) to afford 23 mg (22%) of the title compound. MS [(ESI)] : mass calculated for [C13H16N40,] 277.11 ; [M/Z] found, 278.2 [M+H] [+. 1H] NMR (400 MHz, CD30D) : 7.79-7. 74 [(M,] 2H), 7.45 (dd, [J =] 8.6, 2.0 Hz, [1H),] 4.23-4. 17 (m, 4H), 3.63-3. 58 (m, 4H), 3.01 (s, 3H).

The synthetic route of 3584-66-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2004/22060; (2004); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

18672-03-2, name is 5,6-Dichloro-1H-benzo[d]imidazol-2-amine, 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. Application In Synthesis of 5,6-Dichloro-1H-benzo[d]imidazol-2-amine

EXAMPLE 25 7,8-Dichloro-1,2-dihydro-2,2,3-trimethyl-1,3,5-triazino[1,2-a]benzimidazol-4(3H)-one Reaction of 2-amino-5,6-dichlorobenzimidazole with acetone and methyl isocyanate according to the procedure of Example 1, first paragraph, provided the title compound. In this case, a 10-N-methylcarbamoyl derivative was not isolated from the reaction mixture. The product was recrystallized from acetone to give a solid, mp 220 C. (dec.). The confirmatory elemental analysis is shown in Table III.

The synthetic route of 18672-03-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Union Carbide Corporation; US4497650; (1985); A;; ; Patent; Union Carbide Corporation; US4498920; (1985); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem