Tag: M.W=100-200

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. 45676-04-8, name is 1-tert-Butylimidazole, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H12N2

General procedure: Liquid 1-methylimidazole (a) or 1-phenylimidazole (b) or 1-tert-butylimidazole (c) (1 mol equiv.) was added to a stirring solutionof compound 3 (1 mol equiv.) in 50 mL of CH3CN. The reactionmixture was heated at refluxing temperature for 48 h. Then,the reaction mixturewas reduced in vacuo and the resulting oil wasstirred in diethyl ether. The diethyl ether layer was decanted awayto give ligand 4a, 4b and 4c. The spectral data for these compoundsare consistent with those reported in the literature [25,26,29].

The synthetic route of 45676-04-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Choo, Kar Bee; Lee, Sui Mae; Lee, Wai Leng; Cheow, Yuen Lin; Journal of Organometallic Chemistry; vol. 898; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 104619-51-4, name is Di(1H-imidazol-1-yl)methanimine, 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 104619-51-4, Safety of Di(1H-imidazol-1-yl)methanimine

To a of solution 5-fluoro-2-nitrophenol (4.77 mmol, 0.75 g) in methanol (50 mL), PtO2 (0.24 mmol, 0.06 g) was added. The reaction was flushed with argon followed by hydrogen for fifteen minutes each with constant magnetic stirring. The reaction was then maintained under hydrogen atmosphere at ordinary pressure (balloon) for fifteen hours. Argon was again flushed through the reaction vessel for 15 minutes. Then the reaction contents were filtered quickly over a thin pad of celite which was then immediately washed with methanol (25 mL). The filtrate was concentrated in vacuo yielding an orange residue. The residue was quickly re-dissolved in acetonitrile (50 mL) and di(imidazole-1-yl)methanimine (11.92 mmol, 1.92 g) was added with constant magnetic stirring. The reaction was then placed under argon atmosphere and gently refluxed for six hours. The reaction was concentrated under reduced pressure and silica gel column chromatography (2:1 hexanes/ethyl acetate) provided a crystalline white solid in a 71% yield. The product of the reduction (2-amino-5-fluorophenol) is air unstable and appropriate measures should be taken to minimize air exposure.

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:
Article; Rynearson, Kevin D.; Charrette, Brian; Gabriel, Christopher; Moreno, Jesus; Boerneke, Mark A.; Dibrov, Sergey M.; Hermann, Thomas; Bioorganic and Medicinal Chemistry Letters; vol. 24; 15; (2014); p. 3521 – 3525;,
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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 1072-84-0 as follows. Safety of 1H-Imidazole-4-carboxylic acid

To a solution containing Intermediate 54 (0. 041g) in N, N-DIMETHYLFORMAMIDE (3ML) were added imidazole-4-carboxylic acid (0. 012g, ALDRICH), (1H-1, 2, 3-benzotriazol-1-yloxy) (TRI-1- pyrrolidinyl) phosphonium hexafluorophosphate (PyBop) (0. 053g) and N, N- diisopropylethylamine (0. 03ML). The solution was stirred under nitrogen at room temperature for 18h and was then concentrated in vacuo. The residual gum was purified using an aminopropyl SPE cartridge eluting with methanol followed by chromatography on silica gel (SPE cartridge), eluting with a gradient of 0% to 8% methanol in chloroform, to give the title compound as a yellow solid (0. 031g). LC/MS Rt 2. 32 min, M/Z 549 [MH+]

According to the analysis of related databases, 1072-84-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2004/103998; (2004); 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 934-22-5 as follows. Recommanded Product: 934-22-5

General procedure: A mixture of compound II-1, II-2 or II-3 (2 mmol),SnCl2·2H2O (10 mmol) in EtOAc (15 mL) was refluxed for12 h. When the reaction was complete according to TLCanalysis, the resulting reaction mixture was cooled to room temperature. Subsequently, the reaction mixture wasadjusted to pH 8-9 with saturated aq. NaHCO3 (50 mL).Then the mixture was extracted with EtOAc (2 × 150 mL).The combined organic phase was washed with brine (200mL), dried over anhydrous Na2SO4, and concentrated toafford compounds III-1, III-2 or III-3, which were useddirectly for the next step without further purification. To amixture of 5-amino-1H-benzimidazole (III-1, III-2 or III-3,2 mmol), water (5 mL) and concentrated HCl (12 mol/L,0.51 mL) at 0C, a solution of sodium nitrite (NaNO2, 2.1mmol) in water (10 mL) was added dropwise whilemaintaining the temperature below 5C. After stirring for 20min, a solution of diazonium chloride was prepared.Subsequently, a solution of diazonium chloride was addedgradually to a mixture of phenols (IV-1-IV-10, 2 mmol),sodium hydroxide (NaOH, 2 mmol), ethanol (15 mL) andwater (25 mL) at 0-5C. After the addition of the abovediazonium solution, the mixture was continued to stir for 3-6h until a lot of precipitate was produced. The solid wascollected, washed with water (3×10 mL), dried and purifiedby PTLC to give the target products V-1~V-28.

According to the analysis of related databases, 934-22-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ke, Yazhen; Zhi, Xiaoyan; Yu, Xiang; Ding, Guodong; Yang, Chun; Xu, Hui; Combinatorial Chemistry and High Throughput Screening; vol. 17; 1; (2014); p. 89 – 95;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 36947-68-9, name is 2-Isopropyl-1H-imidazole, molecular formula is C6H10N2, 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. Application In Synthesis of 2-Isopropyl-1H-imidazole

General procedure: To a stirred solution of indole (1.0 mmol)/Imidazole (1.2 mmol) in DMSO was added 1,3-diyne (1.0 mmol), CuI (0.1 mmol), 1,10-phenanthroline (0.05 mmol) and cesium carbonate (1.5 mmol). The reaction mixture was heated at 100 C for 5-16 h and the completion of the reaction was monitored by TLC. After completion of the reaction, it was cooled down to room temperature and then diluted with H2O (5 mL) followed by extraction of the product with EtOAc (3 × 10 mL). The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and the solvent was removed in vacuo. The crude product was purified on a silica gel column using hexane: ethyl acetate as eluent. The Z isomer was crytalised using DCM/EtOH in indole and EtOH in case of imidazole.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 36947-68-9, its application will become more common.

Reference:
Article; Gupta, Sahaj; Agarwal, Piyush K.; Saifuddin, Mohammad; Kundu, Bijoy; Tetrahedron Letters; vol. 52; 44; (2011); p. 5752 – 5757;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 3034-38-6, The chemical industry reduces the impact on the environment during synthesis 3034-38-6, name is 5-Nitro-1H-imidazole, I believe this compound will play a more active role in future production and life.

To a solution of 4-nitro-1H- imidazole (260 mg, 2.299 mmol) in DMF (5 mL) was added 1.0 M NaHMDS/THF (2.53 mL, 2.53 mmol) dropwise at rt. After stirring at rt for 20 min, 1-bromopropan-2-one (315 mg, 2.299 mmol) was added very slowly. The mixture was stirred at rt for ON. Water was added and extracted with EtOAc (4 x 50 mL). The organic layer was concentrated. The residue was purified via silica gel chromatography (12g, DCM-10%MeOH) to give 1-(4-nitro-1H-imidazol-1-yl)propan-2-one (180 mg, 1.064 mmol, 46 % yield). (2333) MS ESI m/z 170.0 (M+H)+ (2334) 1H NMR (499 MHz, CD3OD) delta 8.06 – 8.04 (m, 1H), 7.66 – 7.62 (m, 1H), 5.17 – 5.12 (m, 1H), 2.28 (s, 3H).

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, 5-Nitro-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WATTERSON, Scott Hunter; ANDAPPAN MURUGAIAH SUBBAIAH, Murugaiah; DZIERBA, Carolyn Diane; GONG, Hua; GUERNON, Jason M.; GUO, Junqing; HART, Amy C.; LUO, Guanglin; MACOR, John E.; PITTS, William J.; SHI, Jianliang; VENABLES, Brian Lee; WEIGELT, Carolyn A.; WU, Yong-Jin; ZHENG, Zhizhen Barbara; SIT, Sing-Yuen; CHEN, Jie; (810 pag.)WO2019/147782; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 670-96-2, name is 2-Phenyl-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 670-96-2, COA of Formula: C9H8N2

General procedure: A mixture of Cu(OAc)2 (3.6 mg, 0.020 mmol), ligand II (21.6 mg, 0.020 mmol), and F-PEG (0.25 g, 0.10 mmol) in MeOH (1 mL) was heated to dissolve all the reagents added completely and MeOH was removed under the reduced pressure. H2O (6 mL) was added to the residue and then 4-methoxyphenylboroic acid (1a, 60.8 mg, 0.40 mmol) and imidazole (2a, 13.6 mg, 0.20 mmol) were added. The whole reaction mixture was stirred under an O2 atmosphere at room temperature for 24 h. The mixture was diluted with brine and extracted with AcOEt (30 mL×3). The organic layer was washed with H2O (10 mL×3) and dried over MgSO4. The solvent was removed under the reduced pressure and the residue was purified by SiO2 column chromatography using AcOEt to give N-(4-methoxyphenyl)imidazole (3aa) (26.4 mg, 78%).

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

Reference:
Article; Inamoto, Kiyofumi; Nozawa, Kanako; Kadokawa, Jun; Kondo, Yoshinori; Tetrahedron; vol. 68; 38; (2012); p. 7794 – 7798;,
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. 16681-59-7, name is 2-Bromo-1-methyl-1H-imidazole, A new synthetic method of this compound is introduced below., Quality Control of 2-Bromo-1-methyl-1H-imidazole

General procedure: A mixture of 4-methyl-3-(4-(pyridin-2-ylmethoxy)benzamido)phenyl boronic acid (50 mg, 0.14 mmol), Cs2CO3 (135 mg, 0.41 mmol), Pd(PPh3)4(23.93 mg, 0.02 mmol) and 4-bromo-1H-imidazole (26 mg, 0.18 mmol) was purged with nitrogen before adding degassed dioxane (690 muL) and water (230 muL) and heating in a microwave for 40 min at 150 C. After cooling, the aqueous layer was removed with a pipette, and the organic layer was diluted with DMSO (1 mL) and filtered through a 0.2 mum filter. The filtrate was concentrated to a volume of 1 mL and purified by Gilson HPLC (20-75% MeCN/10 mM NH4OAc in water). The fractions were concentrated and lyophilized to yield the product (19 mg, 0.049 mmol, 35%). 1H NMR (DMSO-d6) delta ppm 12.11 (s, 1H), 9.76 (s, 1H), 8.59 (d, 1H), 7.97 (d, 2H), 7.85 (td, 1H), 7.70 (s, 1H), 7.67 (s, 1H), 7.56 (m, 2H), 7.36 (dd, 1H), 7.21 (d, 1H), 7.15 (d, 2H), 5.27 (s, 2H), 2.18 (s, 3H). LCMS (M+H) = 385.

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:
Review; Yang, Bin; Hird, Alexander W.; Russell, Daniel John; Fauber, Benjamin P.; Dakin, Les A.; Zheng, Xiaolan; Su, Qibin; Godin, Robert; Brassil, Patrick; Devereaux, Erik; Janetka, James W.; Bioorganic and Medicinal Chemistry Letters; vol. 22; 14; (2012); p. 4907 – 4911;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 52099-72-6, The chemical industry reduces the impact on the environment during synthesis 52099-72-6, name is 1-(Prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one, I believe this compound will play a more active role in future production and life.

To a stirred solution of l-Isopropenyl-l,3-dihydro-benzimidazol-2-one (5g, 28.7mmol) in DMF (20ml) was added methyl acrylate (2.8ml, 31.6mmol) followed by benzyltrimethylammonium hydroxide (Triton B, 40 wt% in MeOH, 3.2ml). The resulting solution was stirred at ambient temperature until the reaction was complete. After this time the reaction was poured into water and ethyl acetate. The layers were separated and the aqueous phase was extracted twice more with ethyl acetate. The combined organic layers were dried (MgSCH), filtered and concentrated to give the crude product which was purified via column chromatography (silica gel, 30% ethyl acetate/hexanes). The product-containing fractions were combined and concentrated to give 4.8g (64%) of the desired product.

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2008/147697; (2008); 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. 24134-09-6, name is 5-Bromo-1,2-dimethyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 5-Bromo-1,2-dimethyl-1H-imidazole

To a 50-mL round-bottom flask containing a solution of 5-bromo-1,2-dimethyl-1H-imidazole (440 mg, 2.51 mmol, Intermediate 24, step a) and THF (20 mL) under nitrogen was added isopropylmagnesium chloride in THF (2.0 M, 1.2 mL, 2.4 mmol) dropwise. The mixture was stirred for 0.5 hours at room temperature, and a solution of 4-chloro-N-methoxy-N-methylbenzamide (500 mg, 2.50 mmol, Intermediate 18, step a) in THF (5 mL) was introduced. After stirring for 7.5 hours at room temperature, the reaction was quenched by addition of 10 mL of EtOH, and concentrated under vacuum. The residue was purified by flash column chromatography (silica gel, 50% EtOAc in petroleum, 0-10% MeOH in CH2Cl2) to give the title compound as a white solid.

According to the analysis of related databases, 24134-09-6, the application of this compound in the production field has become more and more popular.

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; Mirzadegan, Taraneh; Ganamet, Kelly; US2014/107097; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem