Category: imidazoles-derivatives

These common heterocyclic compound, 103057-10-9, name is 4-(Chloromethyl)-1-trityl-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. Formula: C23H19ClN2

A.1.1.1. triphenyl[[1-(triphenylmethyl)-1H-imidazol-4-yl]methyl]phosphonium chloride 77.7 g (296 mmol) of triphenylphosphine are added to 670 ml of a solution of 105.5 g (294 mmol) of 4-(chloromethyl)-1-(triphenylmethyl)-1H-imidazole in dimethylformamide. The mixture is heated at 80 C. for 3 hours. The solvent is evaporated and the crude product is taken up in ether and triturated. The precipitate is filtered and dried under vacuum over phosphorus pentoxide. 162 g of product are obtained in the form of yellowish crystals. Melting point=210 C. Yield=89%

The synthetic route of 4-(Chloromethyl)-1-trityl-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Synthelabo; US5552410; (1996); A;,
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. 26832-08-6, name is 1H-Imidazole-4-carboxamide, A new synthetic method of this compound is introduced below., Product Details of 26832-08-6

A suspension of imidazole-4-carboxamide (313 mg) in DMF (3.8 ml) was treated with sodium hydride (60% in mineral oil, 129 mg) at ice-bath temperature and the mixture was stirred at room temperature for 20 min. A solution of 2-[(3S,4S)-4-benzyloxy-3-methanesulfonyloxypentyl]thioanisole (0.92 g) in DMF (7.5 ml) was added and the mixture was stirred at 85 C. for 3 days. The mixture was poured into water and extracted with ethyl acetate. The extract was washed with water, dried and concentrated in vacuo. Column chromatography (dichloromethane:methanol 30:1) gave 1-[(2S,3R)-2-benzyloxy-5-(2-(methylthio)phenyl)-3-pentyl]imidazole-4-carboxamide (1) (96.4 mg, 11.6%) as a pale yellow oil. NMR (CDCl3, d): 1.07 (3H, d, J=6 Hz), 2.0-2.4 (2H, m), 2.44(3H,s) 2.5-2.7(2H, m), 3.6-3.8(1H, m),3.9-4.1(1H, m), 4.39(1H, d, J=12 Hz), 4.58 (1H, d, J=12 Hz),5.37 (1H, s),6.9-7.2 (10H, m), 7.50(1H,d,J=1 Hz), 7.69(1H,d,J=1 Hz). MS (APCI, m/z): 410(M+H)+.

The synthetic route of 26832-08-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tsuji, Kiyoshi; Terasaka, Tadashi; Nakamura, Katsuya; US2004/97571; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 123470-47-3, name is 5,6-Difluoro-1H-benzo[d]imidazole-2(3H)-thione, 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 123470-47-3, Safety of 5,6-Difluoro-1H-benzo[d]imidazole-2(3H)-thione

1-Formyl-4-(2-hydroxyethyl)piperazine (1.11 g, 7.0 mmol), 5,6-difluoro-2-mercaptobenzimidazole (1.30 g, 7.0 mmol), and diisopropylethylamine (3.62 g, 28.0 mmol) were dissolved in propionitrile (50 mL), and cyanomethyltrimethylphosphonium iodide (6.80 g, 28.0 mmol) was added thereto, followed by stirring for one hour at 92 C. under argon. The reaction mixture was allowed to cool and then poured in water (100 mL), followed by extraction with chloroform (100 mL*3). The organic layer was washed with saturated brine and then dried over sodium sulfate anhydrate, and the product was concentrated under reduced pressure. The crude product was crystallized from acetone-ether, to thereby yield 1-[2-(5,6-difluorobenzimidazol-2-ylthio)ethyl]-4-formylpiperazine (1.78 g, yield 78%) as a yellow crystalline powder. mp: 197.0-198.0 C. IR (KBr) cm-1: 3441, 2825, 1648, 1476, 1431, 1363. 1H-NMR (DMSO-d6): delta2.38 (2H, t, J=5.1 Hz), 2.44 (2H, t, J=5.0 Hz), 2.69 (2H, t, J=7.0 Hz), 3.23-3.38 (4H, m), 3.41 (2H, t, J=7.0 Hz), 7,38-7.58 (2H, m), 7.97 (1H, s), 12.8 (1H s). MS (m/z): 326 (M+), 140 (100).

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, 5,6-Difluoro-1H-benzo[d]imidazole-2(3H)-thione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kowa Co., Ltd.; US2005/20606; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 822-36-6, 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. 822-36-6, name is 4-Methyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Preparation 30; [229] Preparation of 3-(4-methyl-imidazol- 1 – yl)-5-trifluoromethyl-phenylamine; [230] 3-amino-5-bromo-benzotrifluoride (17.1g,71.24mmol), 4-methylimidazole (17.6g,213.72mmol), potassium carbonate (9.8g, 71.24mmol), cupper (1. Ig, 17.81mmol), and cupper iode (II) (3.4g, 17.81mmol) were added to N,N-dimethylacetamide (100ml) at room temperature, and mixed therewith at 140~150C for 16 hr. After the reaction was completed, the temperature of the reaction vessel was cooled to RT. Then, ethyl acetate (200ml) was added thereto and mixed therewith for 30 min. The reaction mixture was filtered with Celite, and an organic layer of the filtered solution was washed with water, dried with magnesium sulfate, distilled under vacuum, and washed with n- hexane to give the titled compound as pale white solid.[231] 1H-NMR (CDCl3 delta)= 2.28 (s,3H), 4.04 (br,2H), 6.79 (s,lH), 6.83 (s,lH), 6.92(s,lH), 7.00 (s,lH), 7.77 (s.lH)

The synthetic route of 4-Methyl-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IL-YANG PHARM. CO., LTD.; WO2007/18325; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 1632-83-3, 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. 1632-83-3, name is 1-Methylbenzimidazole, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: In a typical experiment, a predetermined amount of Ni-MOF-74 was added to the 8 mL vial containing a mixture of iodobenzene (0.1030 g, 0.5 mmol), benzothiazole (0.1379 g, 1.0 mmol), Li2CO3 or KCl (1.0 mmol), and diphenyl ether (0.085 g, 0.5 mmol) as standard. 1-Methoxy-2-(2-methoxyethoxy)ethane (diglyme) (1 mL) was added and vial was tightly capped. Reaction mixture was heated at 160C for 24 h. The catalyst loading was based on the molar ratio of nickel/iodobenzene. The reaction yield was monitored by withdrawing aliquots from the reaction mixture at different time intervals, diluting with ethylacetate (2 mL), quenching with an aqueous KOH solution (1%, 1 mL), and then drying over anhydrous Na2SO4 before analyzing by GC with reference to diphenyl ether (internal equation with pure product), and further confirming product identity by GC-MS and NMR. To investigatethe recycle ability of Ni-MOF-74, the catalyst was filtered from the reaction mixture after the experiment, washed with ethylacetate, water, THF, and dried at 140C under vacuum in 8 h. For the leaching test, a catalytic reaction was stopped after 12 h, analyzed by GC, and filtered to remove the solid catalyst. The reaction solution was then stirred for a further 12 h. Reaction progress, if any, was monitored by GC as previously described.

The chemical industry reduces the impact on the environment during synthesis 1-Methylbenzimidazole. I believe this compound will play a more active role in future production and life.

Reference:
Article; Nguyen, Huong T.T.; Doan, Duc N.A.; Truong, Thanh; Journal of Molecular Catalysis A: Chemical; vol. 426; (2017); p. 141 – 149;,
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. 10111-08-7, name is Imidazole-2-carboxaldehyde, A new synthetic method of this compound is introduced below., Computed Properties of C4H4N2O

General procedure: To a mixture of formylimidazole 1 and K2CO3 in DMF, the required bromide or mesylate was added and the reaction mixture was stirred overnight under atmosphere of nitrogen at rt. The resulting suspension was cooled to room temperature (rt) and filtered. Water was added to the filtrate and the resulting solution was extracted with Et20 (3 x 25 mL). The organic layer was dried over MgS04 and evaporated to give the corresponding alkylimidazole-2- carbaldehyde. 1-Isopentyl imidazole-2-carbaldehyde oxime (RS2-37B). Prepared according to the general method A using formylimidazole 1 (0.50 g, 5.2 mmol), K2CO3 (0.72 g, 5.2 mmol), and l-bromo-3-methylbutane (0.94 g, 6.2 mmol) in DMF (20 mL). Yellow oil 2d (0.61 g, 71 %).

The synthetic route of 10111-08-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; THE SCRIPPS RESEARCH INSTITUTE; TAYLOR, Palmer; RADIC, Zoran; FOKIN, Valery; WO2015/57822; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 616-47-7, 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. 616-47-7, name is 1-Methyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 1-methyl-1H-imidazole (200 g, 2.44 mol) in anhydrous THF (2 L) was added dropwise n-BuLi (2.5M, 1.07 L, 2.68 mol) at -78 C with stirring over 2 h. Then perchloroethane (800 g, 0.845 mol) in dry THF (1L) was added dropwise to above solution over 1h at the same temperature. After the starting material was consumed, the mixture was poured into saturated ammonium hydrochloride, extracted with ethyl acetate (800 mL x 3), washed with brine, the organic phase was dried and concentrated to give crude product which was purified by column chromatography on silca gel (PE/ EtOAc = 20:1~5:1) to give the title compound (170 g, 60%) as a yellow oil.

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

Reference:
Article; Chen, Yantao; Goldberg, Frederick W.; Xiong, Jian; Wang, Shujun; Synthesis; vol. 47; 5; (2015); p. 679 – 691;,
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. 2620-76-0, name is 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C19H13BrN2

[0076] l-phenyl-2-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl)- lH-benzo[d]imidazole (3): A mixture of compound (2) (0.70 g, 2 mmol), bis(pinacolate)diborane (0.533g, 2.1 mmol), Pd(dppf)Cl2 (0.060 g, 0.08 mmol) and anhydrous potassium acetate (0.393 g, 4mmol) in 1,4-dioxane (20 mL) was heated at about 80 C under argon overnight. After cooling to room temperature, the whole was diluted with ethyl acetate (~80 mL) then filtered. The solution was absorbed on silica gel, then purified by column chromatography (hexanes/ethyl acetate 5: 1 to 3:1) to give a white solid (0.64 g, in 81% yield).

The synthetic route of 2620-76-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NITTO DENKO CORPORATION; ZHENG, Shijun; SISK, David, T.; HARDING, Brett, T.; CAYAS, Jensen; LI, Sheng; MOCHIZUKI, Amane; CHAE, Hyun, Sik; KHAN, Sazzadur, Rahman; MA, Liping; BOTTGER, Rebecca; WO2011/34967; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 33543-78-1, 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. 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

A solution of ethyl lH-imidazole-2-carboxylate (10.0 g, 71.4 mmol) [Combi-Blocks, SS-7811] in N,N-dimethylformamide (357 mL) was treated with potassium tert-butoxide (74.9 mL, 74.9 mmol, 1.0 M in tetrahydrofuran) dropwise and stirred at 20 C for 1 h. The reaction mixture was then treated with a solution of 0-(4-nitrobenzoyl)hydroxylamine (13.7 g, 74.9 mmol) in N,N-dimethylformamide (120 mL) dropwise via an addition funnel and stirred at 20 C for 3 h. The reaction mixture was filtered and the solid was washed with acetonitrile. The filtrate was evaporated to give the crude product as a slightly oily red solid that was used without further purification.

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

Reference:
Patent; INCYTE CORPORATION; DOUTY, Brent; BUESKING, Andrew W.; BURNS, David M.; COMBS, Andrew P.; FALAHATPISHEH, Nikoo; JALLURI, Ravi Kumar; LEVY, Daniel; POLAM, Padmaja; SHAO, Lixin; SHEPARD, Stacey; SHVARTSBART, Artem; SPARKS, Richard B.; YUE, Eddy W.; (355 pag.)WO2019/79469; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 67085-11-4,Some common heterocyclic compound, 67085-11-4, name is 4-(4-Chlorophenyl)-1-(1H-imidazol-1-yl)butan-2-ol, molecular formula is C13H15ClN2O, 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.

B. Alternatively, a mixture of 1-(4-(4-chlorophenyl)-2-hydroxybutyl)imidazole (1.8 kg, 7.18 mol), 2.25 equivalents of pyridine-sulfur trioxide complex and methylene chloride (8.6 L) stirred in the presence of excess dimethyl sulfoxide (19 L) and triethylamine (9 L) at 20-35 C. for 3 hours. Upon completion of reaction, the mixture was combined with water (76 L) and hexane (34.4 L). The product was isolated, washed with water and hexane and dried to yield 4-(4-chlorophenyl)-1-(imidazol-1-yl)butan-2-one, 1.48 kg (83% yield).

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

Reference:
Patent; Syntex (U.S.A.) Inc.; US5208331; (1993); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem