Month: February 2021

Synthetic Route of 4857-06-1, 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. 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 2-Chloro-1H-benzoimidazole (3.04 g, 20 mmol) was dissolved in dry DMF (15 mL) at 0 C, to the solution was added NaH (0.91 g, 22.7 mmol), and the mixture was stirred for 1 h at 0 C, then halide (21.6 mmol) was added. The mixture was stirred overnight at room temperature and was poured into water (50 mL) and stirred for 1 h, filtrated, washed with water and dried to afford 4a-d.

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, 2-Chloro-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Luo, Yu; Xiao, Feng; Qian, Shijing; Lu, Wei; Yang, Bo; European Journal of Medicinal Chemistry; vol. 46; 1; (2011); p. 417 – 422;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 492-98-8, name is 1H,1’H-2,2′-Biimidazole, 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. Computed Properties of C6H6N4

General procedure: A mixture of H2ATIBDC (0.084 g, 0.150 mmol) and NaOH (0.3 ml, 0.5 mol/l) was dissolved in water (5 ml) and then an aqueous solution of CdCl2¡¤2.5H2O (0.034 g, 0.150 mmol) in water (5 ml) was added whilst stirring. To this solution biim (0.008 g, 0.050 mmol) in methanol (5 ml) was added and then filtered. The compound was obtained from the filtrate with a 68% yield based on H2ATIBDC.

The synthetic route of 1H,1’H-2,2′-Biimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Lei; Wei, Yan; Zhong, Ya-Qiang; Chang, Yan; Meng, Qing-Hua; Ng, Seik Weng; Zhang, Kou-Lin; Inorganica Chimica Acta; vol. 435; (2015); p. 7 – 15;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 2466-76-4, name is 1-(1H-Imidazol-1-yl)ethanone, 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 2466-76-4, HPLC of Formula: C5H6N2O

General procedure: Nucleoside/nucleotide (2; 100 mM) and N-acetyl imidazole (1a;10 equiv) were dissolved in water (pH 8; adjusted with 4 MNaOH). The solution was incubated at r.t. for 4 h, and NMR spectra were periodically acquired. The product was purified byreverse-phase (C18) flash coumn chromatography (eluted at pH4 with 100 mM NH4HCO2/MeCN = 98:2 to 80:20). The fractions containing 5 were lyophilised to yield a white powder.

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-(1H-Imidazol-1-yl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Fernandez-Garcia, Christian; Powner, Matthew W.; Synlett; vol. 28; 1; (2017); p. 78 – 83;,
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. 2963-77-1, name is 4-(1H-Benzo[d]imidazol-2-yl)aniline, This compound has unique chemical properties. The synthetic route is as follows., name: 4-(1H-Benzo[d]imidazol-2-yl)aniline

General procedure: Using a typical scale of 1.0 mmol, 1 (1.0 mmol) was dissolved inanhydrous pyridine (2 mL) in a small round-bottomed flask and themixture was cooled to 40 C after which the acid chloride(2.0 mmol; purchased or prepared as above) in dry THF or DMF(2 mL) was added dropwise over 20 min with vigorous stirring.After 2-6 h the reaction mixturewaswarmed to room temperatureand the solvent reduced under pressure. Without using a work-upthe crude product was purified by column chromatography directlyusing MeOH/DCM mixtures (1:99 to 2:8).

According to the analysis of related databases, 2963-77-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; L’abbate, Fabrizio P.; Mueller, Ronel; Openshaw, Roxanne; Combrinck, Jill M.; de Villiers, Katherine A.; Hunter, Roger; Egan, Timothy J.; European Journal of Medicinal Chemistry; vol. 159; (2018); p. 243 – 254;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 5955-72-6, A common heterocyclic compound, 5955-72-6, name is 2-Chloro-6-nitro-1H-benzo[d]imidazole, molecular formula is C7H4ClN3O2, 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.

Step 3. NaH (60%) in mineral oil was added portion-wise to a stirred suspension of 2-chloro-5- nitro-lH-benzo[d] imidazole (A/1482/81/1) in dry DMF at 0 C under a nitrogen atmosphere The ice-bath was removed, and the reaction mixture was stirred at RT. After 0.5 h the mixture was cooled to 0 C, and 2-trimethylsilylethyoxymethyl chloride (0.38 mL) was added drop-wise. The ice-bath was removed, and the resulting reaction mixture was stirred at RT. After lh, UPLC showed complete conversion. A saturated ammonium chloride solution and EA were added, the organic phase was separated, washed with water, dried over sodium sulfate and the solvent removed under vacuum. The crude material was purified by FC on silica (Snap 100, eluting with Cy EA from 100/0 to 80/20) to give the desired product A/1482/82/1 as yellow oil. Step 4. To a solution of methyl glycolate in dry THF (8 ml) cooled at 0 C was added NaH (60%) in mineral oil. The reaction was stirred at room temperature for 2h. The suspension was cooled at 0 C and a solution of A/1482/82/1 was added dropwise. The reaction mixture was stirred at room temperature for 16h. UPLC showed ~70% reaction completion, and another 1.1 eq of NaH was added. After stirring for 16h, UPLC showed formation of side products. The reaction was stopped, and S. NH4C1 and EtOAC were added. The organic phase was separated, dried and evaporated to give a crude product, which was then purified by silica column (CyHex to CyHex: EtOAc= 85:15). The product named A/1482/83/1 was recovered with a 50% of purity grade (by NMR), with the UPLC retention time of the impurity that same as that of the desired product. Step 5. To a stirred solution oh the A/1482/83/1 cooled to 0 C in THF, a solution of LiOH in water was added dropwise. The mixture was then stirred at room temperature for 2h. UPLC showed complete conversion. The solvent was evaporated under vacuum. The residue was portioned between water and EtOAc, the organic phase was separated and discarded. The water phase was evaporated to give the desired product as the corresponding lithium salt A/1482/84/1.

The synthetic route of 5955-72-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE GENERAL HOSPITAL CORPORATION; ZAHLER, Robert; WESTER, Ronald Thure; BRICKNER, Steven Joseph; WO2014/176258; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 120781-02-4, 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 120781-02-4 as follows.

To the solution of 1.8 g methyl 2-bromo-3-methyl-imidazole-4-carboxylate in mixture ofTHF:MeOH (20 ml_ : 20 mL) at 0C was added a solution of 0.7 g LiOH in H20 (20 mL). After the addition was completed reaction mixture was stirred at 0C for 1 h. Reaction mixture was concentrated under reduced pressure and was diluted with 20 mL of water, acidified with solid KHSO4 and compound was extracted with EtOAc (20 ml x 2). The combined organic layer was washed with brine, dried over Na2S04and concentrated under reduced pressure to afford the title compound as colorless oil (1.5 g, 89.0% yield).1H NMR (400 MHz DMSO-d6): d 7.61 (s, 1 H), 3.82 (s, 3 H).

According to the analysis of related databases, 120781-02-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BASF SE; GOCKEL, Birgit; SOERGEL, Sebastian; KOERBER, Karsten; (152 pag.)WO2019/137995; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1457-58-5, 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. 1457-58-5, name is 2-Methyl-1H-imidazole-5-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

1-(4-Cyano-2-fluorophenyl)-2-methyl-1H-imidazole-4-carboxylic acid A mixture of 2-methyl-1H-imidazole-4-carboxylic acid (400 mg), 4-fluoro-3-fluorobenzonitrile (0.53 g), and K2CO3 (1.3 g) in N,N-dimethylformamide (6 mL) is heated to 100 C. for 30 minutes in a microwave. The crude product is purified by HPLC. LC (method 20): tR=1.24 min; Mass spectrum (APCI): m/z=246 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 2-Methyl-1H-imidazole-5-carboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NEUROCRINE BIOSCIENCES, INC.; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HECKEL, Armin; HIMMELSBACH, Frank; LANGKOPF, Elke; NOSSE, Bernd; ASHWEEK, Neil J.; HARRIOTT, Nicole; US2013/143892; (2013); 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. 57090-88-7, name is 1H-Imidazole-4-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C4H3N3

b) l-(2-Trimethylsilanyl-ethoxymethyl)-lH-imidazole-4-carbonitrile and 3-(2- trimethylsilanyl-ethoxymethyl)-3H-imidazole-4-carbonitrile; A 22-L, four-neck, round-bottom flask equipped with a mechanical stirrer, a temperature probe, and an addition funnel with a nitrogen inlet was charged with IH- imidazole-4-carbonitrile (830 g, 8.91 mol, as prepared in the previous step), potassium carbonate (2.47 kg, 17.8 mol), and acetone (6.0 L). Agitation was initiated and the mixture was cooled to 10 0C with an ice bath. SEMCl (1.50 kg, 9.00 mol) was added through the addition funnel over 210 min to maintain the internal temperature below 15 ¡ãC. The reaction was then allowed to warm to ambient temperature and stirred at ambient temperature overnight (20 h). The reaction mixture was then cooled in an ice bath to 10 ¡ãC and quenched by the slow addition of water (8.0 L) over 30 min to maintain the internal temperature below 30 ¡ãC. The resulting mixture was transferred to a 22-L separatory funnel and extracted with ethyl acetate (2 x 7.0 L). The combined organics were EPO concentrated under reduced pressure at 35 ¡ãC to give the crude product as a dark brown oil, which was purified through a plug of silica gel (16.5 x 20 cm, 2.4 kg silica gel) using 2:1 heptane/ethyl acetate (15 L) as eluent. The fractions containing the product were combined and concentrated under reduced pressure at 35 ¡ãC to afford a mixture of the title compounds as a light brown oil [1785 g, 90percent). The 1H NMR spectrum was consistent with the assigned structure and indicated the presence of a 64:36 ratio of regioisomers.

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 57090-88-7.

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2006/47504; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 1632-83-3, A common heterocyclic compound, 1632-83-3, name is 1-Methylbenzimidazole, molecular formula is C8H8N2, 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.

1-rnethylbenzimidazole (11) (5.0 g, 37.8 mrnol) and N-bromosuccinimide (20.2 g, 113.5 mmol) in 200 mL of THF was heated under reflux for I h. The solvent was removed in rotary evaporator and the residue was recrystallized from EtOAc yielding 8 (7.4 g, 93%) as a white solid. ?H NMR (DMSO-d6) 6 7.77 (d, 1H), 7.65 (d, IH), 7.39 (m, 2H), 3.86 (s, 3H); ?3C NMR (DMSOd5) 6 138.2, 135.4, 131.5, 124.8,124.7, 117.0, 112.3, 33.0; HRMS (ESIQTOF): ni/z Calcd for C8H7N2Br + H: 210.9871, found: 210.9911.

The synthetic route of 1632-83-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VIRGINIA COMMONWEALTH UNIVERSITY; GUPTON, Frank; MARTIN, Alex; SIAMAKI, Ali; BELECKI, Katherine; (28 pag.)WO2016/89845; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 24134-09-6, 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. 24134-09-6, name is 5-Bromo-1,2-dimethyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows.

Example 76: (4-chloro-2-methoxy-3-(4-(trifluoromethoxy)benzyl)quinolin-6-yl)bis(1,2-dimethyl-1H-imidazol-5-yl)methanol To a 25 mL round bottom flask was added 5-bromo- 1 ,2-dimethyl- IH-imidazole (0.22 g, 1.11 mmol) and dry THE (2 mL). The mixture was cooled to -78 C and -BuLi (2.5 M in THF, 0.4 mL, 0,97 mmoi) was added dropwise over one minute. Stirring was continued for 10 minutes at -78 C and a solution of methyl 4-chloro-2-methoxy-3-(4-(trifluoromethoxy)benzyI)quinoline-6- carboxylate (0.12 g, 0.28 mmol, Intermediate 54: step d) in dry THF (4 mL) was added slowly. Stirring was continued at -78 C for 10 minutes then the mixture was cooled to 0 C in an ice bath. The mixture was sirred for 30 minutes then quenched with saturated aqueous NH4CI solution. Water was added and the mixture was extracted with EtOAc (2 x). The EtOAc extracts were combined, washed with brine, dried over Na?S04, filtered and evaporated in vacuo. The residue was purified by FCC (0 – 10 % MeOH/DCM, gradient) to provide the title compound as a tan solid.JH NMR (400 MHz, CD3OD) delta 8.24 (s, I H), 7.84 (s, I H), 7.59 (s, IH), 7.34 (s, 2H), 7.17 (s, 2H), 6.15 (s, 21 1). 4.35 (s, 2H), 4.09 (s, 3H), 3.50 (s, 6H), 2.36 (s, 6H); MS(ESI) 586

The chemical industry reduces the impact on the environment during synthesis 5-Bromo-1,2-dimethyl-1H-imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; LEONARD, Kristi A.; BARBAY, Kent; EDWARDS, James P.; KREUTTER, Kevin D.; KUMMER, David A.; MAHAROOF, Umar; NISHIMURA, Rachel; URBANSKI, Maud; VENKATESAN, Hariharan; WANG, Aihua; WOLIN, Ronald L.; WOODS, Craig R.; FOURIE, Anne; XUE, Xiaohua; CUMMINGS, Maxwell D.; JONES, William Moore; GOLDBERG, Steven; WO2015/57205; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem