Imidazoles-derivatives

A common compound: 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, belongs to imidazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 60-56-0

[Cu(MeimzH)2(phen)(H2O)2]Cl2 (Cu-Met-phen) a solution was prepared by mixing 1 mmol (0.1142 g) of methimazole dissolved in 5 mL of water with 1 mmol (0.1802 g) of o-phenanthroline dissolved in 5 mL of ethanol. To this solution, 1 mmol (0.1705 g) of solid copper(II) chloride dihydrate was slowly added under continuous stirring. The resulting mixture was stirred at room temperature for 2 h. After that, a light green precipitate was formed which was separated, filtered and washed several times with ethanol. After this procedure it was dried in an oven at 60 C. Anal. Calc. for C20H24N6O2S2Cl2Cu: C, 41.48; H, 4.15; N, 14.52; S, 11.06. Found: C, 41.15; H, 4.27; N, 14.78; S, 11.38 %. Yield:75%.

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, 60-56-0, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Urquiza, Nora M.; Islas, M. Soledad; Dittler, Maria Laura; Moyano, Maria A.; Manca, Silvia G.; Lezama, Luis; Rojo, Teofilo; Medina, Juan J. Martinez; Diez, Maximiliano; Tevez, Leonor Lopez; Williams, Patricia A.M.; Ferrer, Evelina G.; Inorganica Chimica Acta; vol. 405; (2013); p. 243 – 251;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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: A mixture of 9-bromo-10-(bromomethyl)anthracene (2) (1 mmol) and the relevant N-alkyl imidazoles(4a-f) or N-benzyl benzimidazoles (7a-e) in THF (15 ml)was refluxed at open condition for 24 h. By this time the products8a-f and 9a-e appeared as yellow precipitates which were isolatedby filtration, washed with little THF, then with ether and were airdried.Yield: 85-89percent (imidazolium salts) and 80-87percent (benzimidazoliumsalts).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 35203-44-2, and friends who are interested can also refer to it.

Reference:
Article; Chatterjee, Tanmay; Kumar, N. Tanmaya; Das, Samar K.; Polyhedron; vol. 127; (2017); p. 68 – 83;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

32673-41-9, A common heterocyclic compound, 32673-41-9, name is 4-Imidazolemethanol hydrochloride, molecular formula is C4H7ClN2O, 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. Methyl 5-tert-butyl-2-hydroxy-3-[(1H-imidazol-4-yl)methyl]-benzoate hydrochloride. 50 g of 1H-imidazole-4-methanol hydrochloride are reacted with 60 g of methyl 5-tert-butyl-2-hydroxybenzoate in 150 ml of concentrated sulfuric acid at 20 C. for 21 hours. The reaction mixture is then cautiously decomposed on ice. The solid product is filtered off, purified by chromatography and then converted into its hydrochloride. 1.1 g of methyl 5-tert-butyl-2-hydroxy-3-[(1H-imidazol-4-yl)methyl]-benzoate hydrochloride is obtained. Yield: 2.8%. M.P.: 185-186 C. NMR (DMSO): delta 1.3(9H,s), 3.45(3H,s), 4.1(2H,s), 7.3(1H,s), 7.75(2H,m), 9.0(1H,s), 10.5 to 13,0 (3H).

The synthetic route of 32673-41-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; U C B Societe Anonyme; US4923865; (1990); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

10111-08-7, 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. 10111-08-7, name is Imidazole-2-carboxaldehyde, This compound has unique chemical properties. The synthetic route is as follows.

A solution of 36 triphenylmethylchloride (640mg, 2.3mmol) in 37 dichloromethane (1mL) was added to a mixture of 2-imidazolecarboxadehyde (200mg, 2.1mmol) and 38 potassium carbonate (1.44g, 10.4mmol) in 39 dimethylformamide (1.5mL). The mixture was stirred at 60C overnight and then cooled down to room temperature. The reaction mixture was extracted with ethyl acetate, the combined extracts were dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by preparative thin layer chromatography eluting with 40% ethyl acetate in 40 hexane to provide 11 9 as a white to light-yellow solid in 32% yield. 1H NMR (300MHz, CDCl3) delta 9.23 (s, 1H), 7.38-7.29 (m, 10H), 7.13-7.10 (m, 6H), 7.02 (s, 1H). The 1H NMR data are consistent with those reported in the literature.17

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; Patanapongpibul, Manee; Zhang, Changde; Chen, Guanglin; Guo, Shanchun; Zhang, Qiang; Zheng, Shilong; Wang, Guangdi; Chen, Qiao-Hong; Bioorganic and Medicinal Chemistry; vol. 26; 16; (2018); p. 4751 – 4760;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1977-72-6, A common compound: 1977-72-6, name is 5-Fluoro-1H-benzo[d]imidazole, belongs to imidazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Intermediate VI-10 5-fluorobenzimidazole (0.28 g, 2.04 mmol) was added to a 150 mL round bottom flask.After stirring potassium carbonate as a base (0.30 g, 2.20 mmol) and acetonitrile as a solvent at 50 C for 40 minutes,After cooling to room temperature, intermediate V (0.43 g, 1.70 mmol) was added and the mixture was warmed to 75 C and the mixture was traced to the end of the reaction.After further concentration, extraction, column chromatography separation, drying and the like, the intermediate X-10 (0.49 g) is obtained, the yield is 73.4%;White solid,

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

Reference:
Patent; Southwest University; Zhou Chenghe; Man Nabaonei¡¤lamohan¡¤laao¡¤yadafu; Wang Juan; (39 pag.)CN110305064; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

288-32-4, Adding some certain compound to certain chemical reactions, such as: 288-32-4, name is 1H-Imidazole, 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 288-32-4.

General procedure: In a representative procedure, organic substrates (1.0 mmol)were added to a solution of acetonitrile/water (1:1, 8 cm3)containing KBr (2 mmol). An accurately weighed amount ofcompound 2 (1.0 mmol) was added to the reaction mixtureat room temperature with continuous stirring. Stirring wascontinued for a further period of ca. 4-5 h. The completionof the reaction was monitored by thin-layer chromatography(TLC). The reaction products as well as the unreactedorganic substrates were separated by column chromatography.The reaction products were analyzed by GC-MS usingbenzophenone as internal standard.

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 288-32-4.

Reference:
Article; Das, Nandita; Chowdhury, Shubhamoy; Purkayastha, Ranendra N. Dutta; Monatshefte fur Chemie; vol. 150; 7; (2019); p. 1255 – 1266;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

41716-18-1, 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. 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 2 1-Methyl-1H-imidazole-4-carboxylic acid 4-[3-hydroxy-4-(3-methyl-butyryl)-2-trifluoromethyl-phenoxymethyl]-benzylamide Mix 1-[4-(4-aminomethyl-benzyloxy)-2-hydroxy-3-trifluoromethyl-phenyl]-3-methyl-butan-1-one hydrochloride (120 mg, 287.2 mumol), 1-methyl-1-H-imidazole-4-carboxylic acid (43.5 mg, 344.6 mumol), 1-hydroxybenzotriazole hydrate (52.8 mg, 344.6 mumol) in anhydrous tetrahydrofuran (4.5 mL). Add triethylamine (72.7 mg, 718 mumol, 100 muL) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (66.1 mg, 344.6 mumol) to the mixture. Stir the reaction mixture at room temperature overnight. Dilute the reaction mixture with water. Extract the mixture with ethyl acetate (3*). Combine the organic layers, wash with brine, dry over sodium sulfate, and concentrate under reduced pressure. Purify the crude residue by flash chromatography (silica gel) eluding with 5percent methanol/ethyl acetate followed by reverse phase chromatography using 90/10 to 20/80 (water/0. 1percent trifluoroacetic acid)/acetonitrile to provide the product as a white solid (75 mg, 153 mumol, 53.4percent yield). MS (m/z): 490 (M+1).

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; Khilevich, Albert; Liu, Bin; Mayhugh, Daniel Ray; Schkeryantz, Jeffrey Michael; Zhang, Deyi; US2010/16373; (2010); 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 3034-50-2 as follows. 3034-50-2

18-1-1 1-Trityl- 1 H-imidazole-4-carbaldehyde; To a solution containing 1 g (10.4 mmol) of 1 H-imidazole-4-carbaldehyde and 3.18 g (1 1 .4 mmol) of trityl chloride suspended in 28 ml. of acetonitrile are added dropwise 2.5 ml. (17.7 mmol) of triethylamine. After stirring for 2 hours at room temperature, 30 ml_ of water are added and the crude reaction product is filtered. 3.2 g in the form of a beige-coloured powder are obtained and used in the following step without further purification.

According to the analysis of related databases, 3034-50-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GALDERMA RESEARCH & DEVELOPMENT; BOUIX-PETER, Claire; SUZUKI, Itaru; PELISSON, Isabelle; COLLETTE, Pascal; TABET, Samuel; LAFITTE, Guillaume; WO2010/52255; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

46006-36-4, 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. 46006-36-4, name is 1H-Benzimidazole-7-carboxylic acid belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Into a 250-mL round-bottom flask, was placed a solution of 1H-1,3-benzodiazole-4- carboxylic acid (4.0 g, 24.67 mmol, 1.00 equiv) in methanol (60 mL), and sulfuric acid (6 mL). The resulting solution was stirred overnight at room temperature then concentrated under vacuum. The resulting solution was diluted with 30 mL of sodium chloride (aq) then extracted with EtOAc (2 x 30 mL) and the organic layers were combined. The pH value of the aqueous layer was adjusted to >7 with NaHCO3 (2M) and was extracted with EtOAc (2 x 30 mL). All EtOAc solutions were then combined and concentrated under reduced pressure to provide methyl 1H-1,3-benzodiazole-4-carboxylate as a red solid (2.5 g, 58% yield).

The synthetic route of 1H-Benzimidazole-7-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LYCERA CORPORATION; AICHER, Thomas, Daniel; PADILLA, Fernando; TOOGOOD, Peter, L.; CHEN, Shoujun; (331 pag.)WO2016/138335; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

54624-57-6,Some common heterocyclic compound, 54624-57-6, name is 2-Bromobenzimidazole, molecular formula is C7H5BrN2, 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) In a 250mL three-necked flask, purged with nitrogen, 0.02mol raw material 2-bromo-1H-benzimidazole, 0.03mol iodobenzene, 0.04mol sodium hydride,0.004mol cuprous iodide and 0.01mol o-phenanthroline dissolved in 100ml 1,3-dimethyl-2-imidazolidinone, the reaction was stirred for 20-30h,After the reaction was completed, water was added and the mixture was extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate,A mixture of petroleum ether and ethyl acetate was used as a eluent shower, the volume ratio of petroleum ether to ethyl acetate in the eluent was 1: 100,Purification by column chromatography gave Intermediate M1; HPLC purity 99.5%, yield 75.8%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromobenzimidazole, its application will become more common.

Reference:
Patent; Jiangsu March Optoelectric Technology Co., Ltd.; Zhang Zhaochao; Li Chong; (51 pag.)CN107417668; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem