Imidazoles-derivatives

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. 96797-15-8, name is 4-Iodo-1-trityl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 96797-15-8

Step 1: Preparation of 2-chloro-5-(1-trityl-H-imidazol-4-yl)pydimidine A 3M solution of ethyl magnesium bromide in diethylether (12.66 mmol) was added to a solution of 4-iodo-1-trityl-1H-imidazole (10.55 mmol) in freshly distilled dry tetrahydrofuran (46.0 mL) in a three necked round bottom flask at room temperature. The reaction mixture was stirred for about 90 minutes and then a 1M solution of zinc chloride (12.66 mmol) was added at room temperature. The solution was stirred for about 90 minutes and then degassed for about 20.0 minutes. Palladium triphenylphosphine (0.61 g, 0.527 mmol) and 5-bromo-2-chloro pyrimidine (11.6 mmol) were added and the reaction mixture was stirred for about 12-14 hrs at about 70 C. The reaction mixture was cooled, diluted with dichloromethane (100.0 mL), washed with aqueous solution of ethylenediaminetetraacetic acid (pH 9), brine, dried over anhydrous sodium sulfate, filtered and concentrated to yield a solid, which was purified by column using ethyl acetate-hexane as eluent to yield the title compound. Yield: 3.0 g (67%).

The synthetic route of 96797-15-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Das, Biswajit; Salman, Mohammad; Kurhade, Santosh Haribhau; Venkataramanan, Ramadass; Kumar, Rajesh; Kapkoti, Gobind Singh; Katoch, Rita; Bandyopadhyay, Anish; Rattan, Ashok; US2009/170790; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 2963-77-1,Some common heterocyclic compound, 2963-77-1, name is 4-(1H-Benzo[d]imidazol-2-yl)aniline, molecular formula is C13H11N3, 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.

General procedure: To a well stirred solution of the corresponding 4-(sub:-1Hbenzo[d]imidazol-2-yl)aniline/4-(3H-imidazo[4,5-b]pyridin-2-yl)aniline (3a-f) (1 equiv) and triethylamine (2.5 equiv) indichloromethane was added the appropriate dicarboxylic acid(1 equiv) followed by propylphosphonic anhydride solution(2.5 equiv; 50% solution in ethyl acetate) at 0 C. The reactionmixture was warmed to room temperature and stirred at roomtemperature for 8h (monitored by TLC and LCMS for completion).The reaction mixture was then washed with water, brine driedover anhydrous sodium sulfate and concentrated under reducedpressure. The residue obtained was then purified by flash chromatographyto afford the desired product in good yield and purity asdescribed below.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(1H-Benzo[d]imidazol-2-yl)aniline, its application will become more common.

Reference:
Article; Janupally, Renuka; Jeankumar, Variam Ullas; Bobesh, Karyakulam Andrews; Soni, Vijay; Devi, Parthiban Brindha; Pulla, Venkat Koushik; Suryadevara, Priyanka; Chennubhotla, Keerthana Sharma; Kulkarni, Pushkar; Yogeeswari, Perumal; Sriram, Dharmarajan; Bioorganic and Medicinal Chemistry; vol. 22; 21; (2014); p. 5970 – 5987;,
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Imidazole | C3H4N2 – PubChem

Reference of 5465-29-2, The chemical industry reduces the impact on the environment during synthesis 5465-29-2, name is 2-Propylbenzimidazole, I believe this compound will play a more active role in future production and life.

2-Propyl-1H-benzo[d]imidazole (Synthetic Communication, 2002, vol. 32, p3703, 246 mg, 1.54 mmol) and (E)-2-[8-(bromomethyl)-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene]propanenitrile (550 mg, 1.54 mmol) obtained in Reference Example 1 were dissolved in DMF (7 mL), potassium carbonate (1.06 g, 7.68 mmol) was added and the mixture was stirred overnight. To the mixture was added water (20 mL), and the precipitated crystals were collected by suction filtration to give the title compound (640 mg, 94%). ESIMS m/z: 438 (M + H)+; 1H NMR (300 MHz, CDCl3,delta): 1.02 (t, J = 7.4 Hz, 3H), 1.77-1.97 (m, 2H), 2.23 (s, 3H), 2.80 (t, J = 7.4 Hz, 2H), 4.73 (d, J = 12.6 Hz, 1H), 5.32-5.48 (m, 3H), 6.51-6.58 (m, 1H), 6.59-6.69 (m, 1H), 6.94-7.07 (m, 3H), 7.11-7.29 (m, 3H), 7.43 (d, J = 7.8 Hz, 1H), 7.78 (d, J = 7.5 Hz, 1H)

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-Propylbenzimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kyowa Hakko Kirin Co., Ltd.; YAMAMOTO, Keisuke; TAMURA, Tomohiro; NAKAMURA, Rina; UENO, Kimihisa; HOSOE, Shintaro; EP2740730; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 71759-89-2, These common heterocyclic compound, 71759-89-2, name is 5-Iodo-1H-imidazole, 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 4-iodoimidazole (50 g, 258 mmoles) in DMF (500 ML) was added triethyl amine (37.7 ml, 270.6 mmoles) and than triphenylmethyl chloride (69.7 g, 250 mmoles). After stirring at room temperature for 48 hours, the solution was poured into ice water (2.5 L). The solid was filtered and pumped on for several hours to yield the crude compound. Ethyl ether (200 ml) was added to the crude compound and the solution was filtered to yield 4-IODO-1-TRITYL-LH-IMIDAZOLE (104.1, 93%) as a white solid. MH+ (437)

Statistics shows that 5-Iodo-1H-imidazole is playing an increasingly important role. we look forward to future research findings about 71759-89-2.

Reference:
Patent; CHIRON CORPORATION; WO2004/96823; (2004); 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. 15965-31-8, name is 5-Chloro-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 5-Chloro-1H-imidazole

A mixture of 4-chloro-lH-imidazole (1.18 g, 11.5 mmol), 1,2,3- trifluoro-5 -nitrobenzene (1.7 g, 9.60 mmol) and potassium carbonate (1.86 g, 13.4 mmol) in DMF (10 mL) was heated at 50 0C for 2 h. The reaction mixture was allowed to cool to rt and was stirred for 16 h. The reaction mixture was diluted with EtOAc (200 mL) and washed with water and brine. The organic layer was dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified using silica gel column chromatography (50% EtOAc/hexane) to afford 4-chloro-l-(2,6-difluoro- 4-nitrophenyl)-lH-imidazole (2.0 gs 80 % yield). LC-MS (M+H)+ = 260.1. 1H NMR (500 MHz, chloroform-^ delta ppm 8.03 – 8.10 (m, 2 H) 7.71 (q, J=1.83 Hz, 1 H) 7.19 (qf J=I.93 Hz, I H).

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 15965-31-8.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MARCIN, Lawrence, R.; THOMPSON, Lorin, A., III; BOY, Kenneth, M.; GUERNON, Jason, M.; HIGGINS, Mendi, A.; SHI, Jianliang; WU, Yong-Jin; ZHANG, Yunhui; MACOR, John, E.; WO2010/83141; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

33529-02-1, name is 1-Decyl-1H-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. category: imidazoles-derivatives

4-Vinylbenzyl chloride (1.00 g, 6.55 mmol) and 1-decylimidazole (1.50 g, 7.20 mmol) were stirred in acetonitrile (40 mL) at reflux for 18 h. Upon cooling, the reaction mixture was concentrated to form a yellow viscous oil and washed with Et2O (3 ¡Á 40 mL). The resulting oil was then dissolved in H2O (40 mL). LiTf2N (2.26 g, 7.87 mmol) was added, and then the resulting mixture stirred at room temperature for 12 h. A yellow oil was then extracted from this aqueous mixture with CH2Cl2 (3 ¡Á 50 mL). The CH2Cl2 layer was then washed with H2O (3 ¡Á 100 mL), dried over anhydrous MgSO4, filtered, and concentrated to give monomer 2c as a light yellow oil (yield: 3.49 g, 88%). 1H NMR (300 MHz, CDCl3): delta8.88 (s, 1H), 7.44 (d, J = 8.2 Hz, 2H), 7.33 (d, J = 8.2 Hz, 2H), 7.24 (dt, J = 12.0, 2.0 Hz, 2H), 6.69 (dd, J = 17.6, 10.9 Hz, 1H), 5.78 (d, J = 17.6, 1H), 5.31 (d, J = 10.8, 1H), 5.31 (s, 2H), 4.16 (t, J = 7.4 Hz, 2H), 1.93-1.76 (m, 2H), 1.39-1.17 (m, 14H), 0.87 (t, J = 7.0 Hz, 3H). 13C NMR (75 MHz, CDCl3): delta139.19, 135.83, 135.58, 131.69, 129.29, 127.41, 122.45, 122.24, 122.08, 117.82, 115.76, 53.46, 50.49, 31.95, 30.18, 29.51, 29.40, 29.34, 28.96, 26.24, 22.77, 14.21. IR (neat): 3146.88, 2927.24, 2856.85, 1560.77, 1456.43, 1348.21, 1182.03, 1133.87, 1053.89, 990.02, 914.86, 830.80, 788.70, 739.55, 653.29. HRMS (ES) calcd. for C24H33F6N3O4S2 (M+ Tf2N-): 605.1817; observed: 605.2435. Since imidazolium-based ionic liquid compounds are known in the literature to have combustion issues for C, H, and N elemental analysis [34], the 1H and 13C NMR spectra for isolated 2c are provided in the Supplementary Data to help confirm its purity.

The synthetic route of 33529-02-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shi, Zhangxing; Newell, Brian S.; Bailey, Travis S.; Gin, Douglas L.; Polymer; vol. 55; 26; (2014); p. 6664 – 6671;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 827320-59-2, name is 1-butylsulfonic-3-methylimidazolium hydrogensulfate, 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 827320-59-2, Formula: C8H16N2O7S2

Synthesis of 1-Sulfobutyl-3-methylimidazole Sulfate Ionic LiquidHydroxylamine Salts: Weigh the 1-sulfobutyl-3-methylimidazolium bisulfate ionic liquidobtained in the second step 5.06 (16.0 mmol) was placed in the reactor. 22.9 ml (32.0mmol of hydroxylamine) was added dropwise to the above ionic liquid in the first step,and the mixture was stirred at a low temperature (? 0 C) for 2 hours, The reactionsolution was evaporated at 70 C to give a white solid product 1-sulfobutyl-3-methylimidazole bisulfate ionic liquid type hydroxylamine salt. After the ionic liquidtype hydroxylamine salt was dried, Weighing 4.25 g, the yield was 69.5%.

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; Hebei University of Technology; WANG, YANJI; LI, ZHIHUI; ZHANG, DONGSHENG; QI, XUDONG; XU, YUANYUAN; YANG, QIUSHENG; ZHAO, XINQIANG; (7 pag.)CN104086474; (2016); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 152628-03-0, 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. 152628-03-0, name is 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 15; PREPARATION OF 2-n-PROPYL-4-METHYL-6-(1-BENZIMIDAZOLE-2-YL) BENZIMIDAZOLE (FORMULA XI); 5 g of 2-n-propyl-4-methyl-benzimiclazoltheta-6-carboxylic acid of Formula III, obtained in Example 1 , and 2.6 g of o-phenylenediamine, were charged into a round bottom flask containing 15 g of polyphosphoric acid (PPA). Reaction mass was heated to 150-155 C and maintained for 4-5 hours. Cooled the reaction mass to 70-80 C and charged 50 ml of water. Stirred for 45-60 minutes at the same temperature and then cooled to 10-15 C. Reaction mass pH was adjusted to 5-6 with 10% aqueous sodium hydroxide solution (200 ml) and stirred for 15-30 minutes. Filtered the solid and washed with 10 ml of water.The wet solid was charged into a flask and 50 ml of water was added. The contents were heated to 70-80 C and stirred for 30-45 minutes. Cooled to 25-35 C and stirred for 30-45 minutes. Filtered the solid and washed with 10 ml of water. Dried the solid at 50-55 C for 4-5 hours to afford 7.2 g of the title compound.

The chemical industry reduces the impact on the environment during synthesis 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; DR. REDDY’S LABORATORIES LTD.; DR. REDDY’S LABORATORIES, INC.; WO2006/44754; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 88427-96-7,Some common heterocyclic compound, 88427-96-7, name is 4-(2-Methyl-1H-imidazol-1-yl)benzaldehyde, molecular formula is C11H10N2O, 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.

Reference example 5-3 2-Methyl-5-(trifluoromethoxy)-1H-indole To the compound of Reference example 5-2 (2.09 g, 5.69 mmol) were added trifluoroacetic acid (22 ml) and thiosalicylic acid (878 mg, 5.69 mmol), and the mixture was stirred for 3 hours at 50¡ãC. The reaction mixture was diluted with ethyl acetate and neutralized with 1N aqueous sodium hydroxide solution and the mixture was separated by a separating funnel. The organic layer was washed with 1N aqueous sodium hydroxide solution and saturated brine, dried over anhydrous sodium sulfate and filtered. The solvent was removed in vacuo and the residue was purified by silica gel column chromatography to give the subject compound (727 mg, 59 percent). 1H NMR (CDCl3, 400 MHz) delta 7.95 (brs, 1H), 7.35 (brs, 1H), 7.24 (d, 1H, J = 8.7 Hz), 6.97 (brd, 1H, J = 8.7 Hz), 6.24-6.22 (m, 1H), 2.45 (s, 3H).

The synthetic route of 88427-96-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dainippon Sumitomo Pharma Co., Ltd.; EP1837329; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 3314-30-5, name is 1H-Benzo[d]imidazole-2-carbaldehyde, 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 3314-30-5, SDS of cas: 3314-30-5

General procedure: The equimolar aldehyde 3a?3d (1 mmol) and substituted phenylhydrazine 5a?5s (1 mmol) weremixed in CH3OH (10 mL) and stirred at room temperature [18]. After about 2 h, the reaction wascompleted (monitored by TLC). The residual crude was purified via silica gel column chromatogramusing a gradient mixture of petroleum ether and ethyl acetate to obtain the pure target compounds6a?6ai (in 45?80percent yield).

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

Reference:
Article; Wang, Xing; Chen, Yong-Fei; Yan, Wei; Cao, Ling-Ling; Ye, Yong-Hao; Molecules; vol. 21; 11; (2016);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem