Tag: M.W=100-200

Electric Literature 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.

Step A: To a mixture of 4-nitro-lH-imidazole (1.5 g, 13.27 mmol) and TEA (2 mL, 14.59 mmol) in DMF (12 mL) at 0 C was added trityl chloride (3.7 g, 13.27 mmol). The mixture was allowed to warm to rt and was stirred for 1 h. The mixture was poured onto ice and 1 N aq NaOH (2 mL) was added. The solid was collected by filtration washing with water to afford 4-nitro-l -trityl- lH-imidazole as a solid (4.58 g, 96%).

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

Reference:
Patent; AMBIT BOISCIENCES CORPORATION; HADD, Michael, J.; WO2012/30914; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 36947-68-9, name is 2-Isopropyl-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. SDS of cas: 36947-68-9

EXAMPLE 11 2-Isopropyl-1-(6-methylergolin-8beta-ylmethyl)imidazole 0.9 g of 50% sodium hydride in an oil was added to a mixture of 4.0 g of 2-isopropylimidazole and 40 ml of dimethylformamide, and the mixture was stirred for 30 minutes. 2.0 g of 6-methylergolin-8beta-ylmethyl tosylate was added to the mixture which was then heated on a water bath for 2 hours. The solvent was distilled off under reduced pressure, and water was added to the residue. The precipitated crystals were filtered, washed with water and purified by silica gel column chromatography (eluted with acetone). The crystals thus obtained were dissolved in methanol, and isopropyl alcohol was added thereto. The mixture was concentrated and allowed to cool to obtain 0.6 g of the titled compound as colorless needles having a melting point of 283-288 C. (with decomposition). NMR (CDCl3) delta: 1.18 (1H, q, J=11.7 Hz), 1.34 (3H, d, J=6.7 Hz), 1.35 (3H, d, J=6.7 Hz), 1.80-3.09 (7H, m), 2.43 (3H, s), 3.37 (1H, dd, J=14.3, 4.4 Hz), 3.80 (2H, d, J=6.8 Hz), 6.65-7.25 (6H, m). Elementary Analysis for C22 H28 N4: Calc’d: C. 75.82; H, 8.10; N, 16.03. Found: C, 76.15; H, 8.39; N, 16.25.

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

Reference:
Patent; Maruko Seiyaku Co., Ltd.; US4713457; (1987); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 46006-36-4, name is 1H-Benzimidazole-7-carboxylic acid, molecular formula is C8H6N2O2, 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. SDS of cas: 46006-36-4

Step 1: (lH-Benzo[d]imidazol-4-yl)(l-methyl-lH-spiro[chromeno[4,3- c] pyrazole-4,4 ‘-piperidine] -1 ‘-yl)methanone To a solution of l-methylspiro[chromeno[4,3-c]pyrazole-4,4′-piperidine] (211 mg, 0.830 mmol), lH-benzimidazole-4-carboxylic acid (134 mg, 0.830 mmol) and triethylamine (346 mu?, 2.50 mmol) in dichloromethane (2 mL) was added HATU (314 mg, 0.830 mmol) in one portion and the mixture was stirred for 12 hours. The reaction mixture was treated with 1M NaOH (1 mL) for 10 minutes. Dichloromethane (5 mL) was added. The two layers were separated and the aqueous layer was extracted with dichloromethane (2 5 mL). The organic layers were combined, washed with brine, dried over MgS04, filtered and evaporated to yield a residue that was purified on silica using a gradient of 0.5-30% MeOH in dichloromethane to yield (1 H-benzo[d]imidazol-4-yl)(l -methyl- 1 H-spiro[chromeno[4,3-c]pyrazole-4,4’- piperidine]- -yl)methanone. ESI-MS m/z calc. 399.5, found 400.5 (M+l)+. Retention time: 1.12 minutes (4 min run).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 46006-36-4, its application will become more common.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; HADIDA-RUAH, Sara, Sabina; GROOTENHUIS, Peter, Diederik, Jan; MILLER, Mark, Thomas; ANDERSON, Corey; PONTILLO, Joseph; KALLEL, Edward, Adam; NUMA, Mehdi, Michael, Djamel; FRIEMAN, Bryan, A.; McCARTNEY, Jason; WORLEY, Jennings, Franklin; ARUMUGAM, Vijayalaksmi; UY, Johnny; HILGRAF, Nicole; BEAR, Brian, Richard; WO2013/67248; (2013); 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.

A solution of 2-mercaptobenzimidazole (0.15 g, 1.0 mmol) in methanol(10 mL) was added to a solution of BiI3 (0,294 g, 0.5 mmol) inacetonitrile (10 mL). The resulting solution was stirred for 3 h at 50 C.The solution obtained was filtered and slowly evaporated until the redcrystals were isolated. Yield: % 79.5; mp, 234-238 C; mw, 1780, 19 g/mol. Elemental Anal. Calc. for C28H24Bi2I6N8S4: C, 18.89; H, 1.36; N,6.29; S, 7.20. Found: C, 18.92; H, 1.38; N, 6.32; S, 7.29. UV-Vis(DMSO): lambdamax (logepsilon): 312.50 (5.28), 257.00 (4.90). IR (cm-1): 3198 m,2361m, 1620m, 1491s, 1450s, 1396m, 1344m, 1252w, 1165m, 1149w,1009m, 974m, 926w, 810w, 742s, 671m, 596s, 567w, 410m. 13C NMR[400 MHz, DMSO-d6, delta(ppm)]: 168.71 (C]S), 133.17 (C4, C5), 123.34(C7, C8), 110.49 (C6, C9). Soluble in methanol, acetonitrile, acetone,tetrahydrofuran, dimethylsulfoxide. LambdaM=45.2 Omega-1·cm2·mol-1.

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

Reference:
Article; Ozturk; Banti; Hadjikakou; Panagiotou; Tasiopoulos; Inorganica Chimica Acta; vol. 497; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 3034-38-6, name is 5-Nitro-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 3034-38-6, SDS of cas: 3034-38-6

Preparative Example 23. A mixture of commercially available 4-nitroimidazole (5 g) and Pd/C (10wt%, 500 mg) in a premixed solution of acetyl chloride (4 mL) in MeOH (100 mL) was hydrogenated in a Parr shaker at 35 psi for 5 h. The mixture was filtered through celite and concentrated to give a black oil. [MH]+ = 115. This oil and methyl acetylpyruvate (6.4 g) were stirred in AcOH (7O mL) and MeOH (7O mL) at 65C for 18 h. The resulting mixture was absorbed on silica and purified by chromatography (silica, CH2Cl2/MeOH). Further purification of the resulting residue by chromatography (silica, EtOAc) afforded 2-methyl- imidazo[l,5-a]pyrimidine-4-carboxylic acid methyl ester as an orange solid (120 mg, 1.4%). [MH]+ = 192.

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; ALANTOS PHARMACEUTICALS HOLDING, INC.; WO2008/63671; (2008); 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. 4856-97-7, name is (1H-Benzoimidazol-2-yl)methanol, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H8N2O

Preparation of (1-allyl-1H-benzoimidazol-2-yl)-methanol: To a solution of (1H-benzoimidazol-2-yl)-methanol (501 mg, 3.38 mmol) and allyl bromide (0.29 mL, 3.38 mmol) in DMF (15 mL) was added N,N-diisopropylethylamine (0.71 mL, 4.06 mmol). The reaction mixture was stirred at 60° C. overnight. Then the mixture was cooled to room temperature and quenched with saturated NaHCO3 (25 mL). Then it was extracted with CH2Cl2 (3*25 mL). The combined organic layer was washed with brine (2*25 mL), dried (MgSO4), filtered, concentrated, and dried in vacuo to afford a brown oil. Purification by flash column chromatography on silica gel using 2percent CH3OH/CH2Cl2 afforded the product as a yellow oil (180 mg, 28percent). 1H NMR (CDCl3) delta 4.85 (br s, 5H), 4.98 (d, 1H, J=17.1 Hz), 5.17 (d, 1H, J=10.5 Hz), 5.88-6.01 (in, 1H), 7.20-7.26 (m, 3H), 7.66 (t, 1H, J=3.9 Hz).

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 4856-97-7.

Reference:
Patent; Bridger, Gary; Kaller, Al; Harwig, Curtis; Skerlj, Renato; Bogucki, David; Wilson, Trevor R.; Crawford, Jason; McEachern, Ernest J.; Atsma, Bem; Nan, Siqiao; Zhou, Yuanxi; Schols, Dominique; Smith, Christopher D.; Di Fluri, Maria R.; US2004/19058; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 35203-44-2, 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 35203-44-2 as follows.

General procedure: All of the imidazolium salts were synthesized with good yields (>85percent, see Supporting Information online) by thequaternization of N-substituted imidazole with corresponding iodide alkane, according to Scheme 1. Take 1-hexadecyl-3-methylimidazolium iodide (1a) for example: the mixture of 1-methylimidazole and 1-iodohexadecane was dissolved in acetone. Then the solution was placed into a 58 mL Teflon-lined, stainless-steel autoclave and heated at 100 °C for 12 h. The final product was obtained by multiple crystallizations from diethyl ether. The purity of all the imidazolium salts was confirmed by 1H NMR and elemental analysis (see Supporting Information online).

According to the analysis of related databases, 35203-44-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Meng; Pan, Xu; Chen, Jian; Dai, Songyuan; Science China Chemistry; vol. 58; 12; (2015); p. 1884 – 1890;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 3012-80-4,Some common heterocyclic compound, 3012-80-4, name is 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde, molecular formula is C9H8N2O, 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.

Add 1.00 mmol of N-methyl-benzimidazole-2-carbaldehyde (0.1700 g) to a 15 mL capacity of polytetrafluoroethyleneIn the reaction kettle, after adding 10 mL of methanol to dissolve,Add 0.5 mmol of cobalt chloride tetrahydrate (0.119 g),Add 0.25 mmol under stirring2-Aminomethylpyridine (26 muL), stirring for 3 minutes, sealed, placed in an oven at 160 ° C for 48 h, then slowly cooled to obtain yellow block crystals (about 10 h down to room temperature), yield 46 percent (based on 2-aminomethylpyridine).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde, its application will become more common.

Reference:
Patent; Guangxi Normal University; Zeng Minghua; Zhu Zhonghong; (18 pag.)CN108164566; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 33468-67-6, These common heterocyclic compound, 33468-67-6, name is 2-Methyl-4-(trifluoromethyl)-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.

a) To a vial was added 2-methyl-4-(trifluoromethyl)-1H-imidazole (750 mg, 5 mmol), 5 mL of THF, 2.5 mL of DMF, and K2CO3 (2.07 g, 15 mmol). To this mixture was slowly added ethyl bromoacetate (1.00 g, 6 mmol). After 2 hours, the slurry was diluted with EtOAc, filtered on Celite, and concentrated. The residue was purified by flash chromatography (SiO2, 80 g column, eluting with 15-100% EtOAc in hexanes) to provide 476 mg (40%) of the title compound as a colorless oil. 1H NMR (400 MHz, CDCl3) delta 7.20 (s, 1H), 4.61 (s, 2H), 4.28 (q, J=7.0 Hz, 2H), 1.63 (s, 3H), 1.31 (t, J=7.0 Hz, 3H); MS: (ES) m/z calculated for C9H12F3N2O2 [M+H]+ 237.1, found 237.1. The regiochemistry of the system was confirmed by nOe between the alpha-methylene and both the imidazole ring and methyl protons.

The synthetic route of 33468-67-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ChemoCentryx, Inc.; Chen, Xi; Dragoli, Dean R.; Fan, Pingchen; Li, Yandong; Powers, Jay P.; Punna, Sreenivas; Tanaka, Hiroko; Zhang, Penglie; US2014/57937; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 75370-65-9,Some common heterocyclic compound, 75370-65-9, name is 4-Amino-1H-benzo[d]imidazol-2(3H)-one, molecular formula is C7H7N3O, 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 29f (0.48g, 1.85 mmol) in THF (20mL) was added CDI (2.1 mol eq, 0.63g) and the mixture was heated for 5 h. 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 (0.78 g, quantitative yield) was dissolved in DMF (20 mL) and the bicyclic amine la was added (0.8 mol eq, 0.26g), then the mixture obtained was heated at 100C overnight. The solvent was removed at reduced pressure and the residue was purified by chromatography (9.5:0.5 EtoAc:MeOH) to obtain the product as a pale yellow solid (0.14g, 0.32 mmol, 15% Yield). 1HNM (DMSO, 400 MHz) delta 1.63 (m, 6H), 3.09 (m, 4H), 4.36 (d, 2H, J=6), 6.61 (d, 1H, J=8), 6.84 (t, 2H), 6.95 (d, 1H, J=6), 7.42 (d, 1H, J=8), 7.87 (d, 1H, J=6), 8.37 (s, 1H), 10.01 (bs, 1H), 10.59 (bs, 1H). [M+1] 434.91 (C20H21F3N6O2 requires 434.41).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Amino-1H-benzo[d]imidazol-2(3H)-one, its application will become more common.

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