Category: imidazoles-derivatives

Electric Literature of 3543-73-5, A common heterocyclic compound, 3543-73-5, name is Ethyl 4-(5-amino-1-methyl-1H-benzo[d]imidazol-2-yl)butanoate, molecular formula is C14H19N3O2, 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.

Example-5 Preparation of Ethyl 4-{5-[bis(2-hydroxyethyl)amino]-1-methyl-1H-benzimidazol-2-yl}butanoate (III) Ethyl 4-[5-amino-1-methyl-1H-benzimidazol-2-yl)butanoate (II, 200.0 g, 0.763 mol) was added to DM Water (1.1 L). Aqueous sodium acetate.3H2O (20.0 g sodium acetate.3H2O in 100 mL DM water) and acetic acid (400 mL) was added and agitated till complete dissolution of compound of the formula II. The reaction mixture was cooled to 0-5 C. and ethylene oxide (270.0 g, 6.12 mole) was added maintaining the temperature of the reaction mixture at 0-5 C. The reaction mixture was stirred at 0-5 C. for 5 hours. The temperature of reaction mixture was raised to 20-25 C. and agitated at 20-25 C. for 18 hours. After completion of the reaction, dichloromethane (2.0 L) was added at 20-25 C. followed by addition of aqueous solution of potassium carbonate (440.0 g potassium carbonate in 1.1 L DM water) portion wise at 20-25 C. to control the evaluation of effervescence and agitated at 20-25 C. for 5-10 minutes. The layers were separated. The organic layer (dichloromethane) was washed with DM water (1.0 L) twice and organic layer was concentrated under vacuum at 40-50 C. till viscous mass is obtained. The viscous mass was dissolved in acetone (1.0 L), cooled to 0-5 C. and agitated at 0-5 C. for 1 hour. The solid separated out was filtered, washed with chilled (0-5 C.) acetone (200.0 mL) and dried at 40-50 C. under vacuum for 6 hours to give the title compound (III, 210.0 g; 78.53%), with a purity of 99.06%.

The synthetic route of 3543-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FRESENIUS KABI ONCOLOGY LIMITED; MISHRA, Bhuwan Bhaskar; KACHHADIA, Nikunj Shambhubhai; TOMAR, Vinod Singh; LAHIRI, Saswata; US2014/121383; (2014); 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. 87941-55-7, name is 4-Bromo-1-trityl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., name: 4-Bromo-1-trityl-1H-imidazole

To a single-necked flask was added 4-bromo-1-trityl-1H-imidazole (1.5 g, 3.9 mmol)Sodium carbonate (1.2 g, 11.7 mmol),2-formylbenzeneboronic acid (864 mg, 5.8 mmol) and DMF (10 ml)Water (2 ml), the reaction system was filled with nitrogen,Tetrakis (triphenylphosphine) palladium (242 mg, 0.195 mmol) was added under nitrogen,90 C for 16 h, add water,Ethyl acetate, the combined organic layers were dried over anhydrous sodium sulfate, the solvent was concentrated,Purification by column chromatography on silica gel afforded compound 8 (930 mg, yield 58%).

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 87941-55-7.

Reference:
Patent; Hinova Pharmaceuticals Inc.; Fan, Lei; Chen, Ke; Li, Xinghai; Chen, Yuanwei; (24 pag.)CN106256830; (2016); 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. 5993-91-9, name is (1H-Benzo[d]imidazol-2-yl)methanamine dihydrochloride, A new synthetic method of this compound is introduced below., Application In Synthesis of (1H-Benzo[d]imidazol-2-yl)methanamine dihydrochloride

[0118] To a stirred solution of (2-aminomethyl)benzimidazole dihydrochloride hydrate (5.96 g, 27.1 mmol) in dry MeOH (225 mL) was added 6,7-dihydro-5H-quinolin-8-one (3.99 g, 27.1 mmol) and the mixture stirred at room temperature for 69 h. To the resultant solution was added sodium borohydride (2.06 g, 54.2 mmol) in two portions and the mixture stirred for 1.5 h. The reaction mixture was concentrated in vacuo and diluted with CH2Cl2 (150 mL). The organic layer was washed with saturated aqueous sodium bicarbonate (200 mL), the aqueous layer extracted with CH2Cl2 (2×50 mL) and the combined organic layers dried (Na2SO4), filtered, and concentrated in vacuo. Purification by column chromatography on silica gel (CH2Cl2/MeOH, 99:1 followed by 98:2 and 96:4) gave the intermediate amine (3.59 g, 50%) as a yellow foam. 1H NMR (CDCl3) delta 1.66-1.90 (m, 3H), 1.91-2.00 (m, 1H), 2.00-2.17 (m, 1H), 2.33-2.69 (br m, 1H), 3.88-3.96 (m, 1H), 4.37 (d, 1H, J=3.0 Hz), 7.18-7.26 (m, 4H), 7.48 (d, 1H, J=6.0 Hz), 7.58-7.78 (br m, 1H), 8.55-8.58 (m, 1H); 13C NMR (CDCl3) delta 19.66, 29.12, 30.24, 46.62, 57.28, 122.21, 122.83, 133.55, 138.07, 146.98, 156.17, 157.73.

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:
Patent; Bridger, Gary; Skerlj, Renato; Kaller, Ai; Harwig, Curtis; Bogucki, David; Wilson, Trevor R.; Crawford, Jason; McEachern, Ernest J.; Atsma, Bem; Nan, Siqiao; Zhou, Yuanxi; Schols, Dominique; Smith, Christopher Dennis; Di Fluri, Maria Rosaria; US2003/220341; (2003); 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. 53710-78-4, name is 1-(3-Chloropropyl)-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C6H9ClN2

1-(3-Chloropropyl)-1H-imidazole (596 mg, 4.12 mmol), potassium carbonate (660 mg, 4.775 mmol) and potassium iodide (106 mg, 0.64 mmol) were added to a stirred solution of cis-4-amino-5-chloro-2-methoxy-N-(3-methoxypiperidin-4-yl)benzamide (1 g, 3.188 mmol) in N,N-dimethylformamide (20 mL) in order. The reaction mixture was heated to 90 C for 12 h and then cooled to room temperature and extracted with ethyl acetate and water. The organic layer was dried over anhydrous MgSO4 and evaporated in vacuo. The residue was purified by column chromatography (chloroform:acetone = 4:1) to obtain the target compound (700 mg, 52% yield). 1H NMR (400 MHz, CDCl3): delta 8.19 (d, J = 8.4 Hz, 1H), 8.06 (s, 1H), 7.49 (s, 1H), 7.03 (s, 1H), 6.92 (s, 1H), 6.28 (s, 1H), 4.49 (bs, 2H), 4.19-4.08 (m, 1H), 4.08-3.92 (m, 2H), 3.85 (s, 3H), 3.44-3.38 (m, 4H), 2.99-2.83 (m, 1H), 2.78-2.65 (m, 1H), 2.35-2.18 (m, 2H), 2.18-2.03 (m, 2H), 1.99-1.67 (m, 4H). 13C NMR (400 MHz, CDCl3): delta 163.75, 157.56, 146.76, 137.41, 132.92, 129.28, 112.45, 111.44, 97.85, 57.14, 55.96, 54.19, 53.74, 51.44, 48.15, 44.53, 28.14, 27.73. HRMS (FAB): calcd for C20H28ClN5O3 [M+H]+ 422.1954, found 422.1955.

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 53710-78-4.

Reference:
Article; Park, Jung Sang; Im, Weonbin; Choi, Sunghak; Park, Sook Jin; Jung, Jun Min; Baek, Ki Seon; Son, Han Pyo; Sharma, Satyasheel; Kim, In Su; Jung, Young Hoon; European Journal of Medicinal Chemistry; vol. 109; (2016); p. 75 – 88;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 103057-10-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 103057-10-9 name is 4-(Chloromethyl)-1-trityl-1H-imidazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

REFERENCE EXAMPLE 34 Ethyl 5,6-Dimethoxy-1-(1-trityl-4-imidazolyl)methyl-1H-indazole-3-carboxylate In 5000 ml of dimethyl sulfoxide was suspended 250.2 g of ethyl 5,6-dimethoxyindazole-3-carboxylate, and 40.2 g of lithium methoxide was added to the suspension, followed by stirring at room temperature for 1 hour. A solution of 447.8 g of 4-chloromethyl-1-tritylimidazole in 2000 ml of dimethyl sulfoxide was added dropwise thereto at room temperature over 10 minutes. After stirring at room temperature for 2 hours, 4.2 g of lithium methoxide and 44.8 g of 4-chloromethyl-1-tritylimidazole were further added thereto, followed by stirring at room temperature for 1 hour. The reaction mixture was poured into 30000 ml of ice-water while stirring. A precipitated crystal was collected, washed with three 2000 ml portions of water, and dried. The solid was dissolved in 10000 ml of chloroform, and the solution was dried over sodium sulfate, filtered, and the solvent was evaporated. The residue was purified by silica gel column chromatography (chloroform:ethanol=50:1) and recrystallized from chloroform/isopropyl alcohol to yield 222.0 g of the title compound as a colorless prism crystal.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(Chloromethyl)-1-trityl-1H-imidazole, and friends who are interested can also refer to it.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP624584; (1994); 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. 7152-24-1, name is 2-(Methylthio)benzimidazole, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H8N2S

General procedure: Metallic Na (76 mg,3.3 mmol) was added to t-BuOH (30 ml), and the mixturewas heated under reflux until effervescence ceased. Thenazole 3b-d or 6b,d,e (3 mmol) and 3,5-dibromo-1-(1,1-dioxidothietan-3-yl)-1H-1,2,4-triazole (1) (0.99 g, 3 mmol)were added. The reaction mixture was heated under refluxfor 2 h (for compounds 4b-d, 7d,e) or 3 h (for compound7b). The solvent was evaporated under reduced pressure,and H2O (15 ml) was added to the residue. The precipitatewas filtered off, dried at 60C, and recrystallized from asuitable solvent.

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 7152-24-1.

Reference:
Article; Makarova, Nadezhda N.; Klen, Elena E.; Khaliullin, Ferkat ?.; Chemistry of Heterocyclic Compounds; vol. 55; 9; (2019); p. 823 – 826; Khim. Geterotsikl. Soedin.; vol. 55; 9; (2019); p. 823 – 826,4;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 870837-18-6, These common heterocyclic compound, 870837-18-6, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, 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 THF solution of C6 (R21 = R21 = Me and R4 = Me1 R6 = H and R7 = p- F-Ph) will be added LDA (1.1 eq) at -78 0C and the solution will be stirred for 30 min before C7 (R8 = H; R10 = 3-MeO-phenyl; R9 = 4-(4-Methylimidazol-1-yl)) will be added. After the starting material is consumed, the reaction mixture will be treated with triflic anhydride and triethyl amine before the volatiles will be removed and residue chromatographed to give a product which upon TFA deprotection and purification will give compound C8 (R21 = R21 = Me and R4 = Me, R6 = H and R7 = p-F-Ph, R8 = H; R10 = 3-MeO-phenyl; R9 = 4-(4-Methylimidazol-1-yl)).

The synthetic route of 870837-18-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; WO2009/5729; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 716-79-0, A common heterocyclic compound, 716-79-0, name is 2-Phenyl-1H-benzo[d]imidazole, molecular formula is C13H10N2, 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 28 mL of dimethyl sulfoxide was added 2.8 g (14 mmol, 1 equivalent) of 2-phenyl-1H-1,3-benzodiazole, 1.6 g (28 mmol, 2 eq.) Of potassium hydroxide, 0.12 g (0.72 mmol, 5 molpercent) of potassium iodide were sequentially added thereto, followed by cooling and stirring, 3.0 mL (28 mmol, 2 equivalents) of butane bromide was slowly added thereto, and the mixture was heated to room temperature and agitated for 4 hours. After completion of the reaction, 60 mL of water and 60 mL of ethyl acetate were added to the reaction mixture, After further washing with 60 mL of water, the solution was concentrated and purified by silica column chromatography to obtain 3.3 g (91percent) of 1-butyl-2-phenyl-1H-1,3-benzodiazole.

The synthetic route of 716-79-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Samyang Co., Ltd.; Oh Cheon-rim; Lee Jae-hun; Kwon Jae-gwan; Lee Deuk-rak; Lee Won-jung; (17 pag.)KR2018/77354; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 583-39-1, name is 2-Mercaptobenzimidazole, 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 583-39-1, Safety of 2-Mercaptobenzimidazole

A mixture of 0.1 g of benzimidazole-2-thione, 0.374 g of benzyl acetate 1, and 5 mL of methanol was kept at room temperature for 20 days. The precipitate was filtered off, washed with methanol, and dried in air. Yield 0.21 g (54%), mp 243-245C (mp 244-245C [13]). 1H NMR spectrum (CDCl3), delta, ppm: 1.42 s (36H, CMe3), 5.18 s (2H,OH ), 5.52 s (4H, CH2N), 7.12-7.25 m (4H, ArH), 7.40 s (4H, ArH).

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; Gataullina; Mogilevtseva; Nugumanova; Bukharov; Tagasheva; Deberdeev, R. Ya.; Russian Journal of General Chemistry; vol. 87; 9; (2017); p. 1919 – 1923; Zh. Obshch. Khim.; vol. 87; 9; (2017); p. -1435 – -1439,5;,
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. 14741-71-0, name is Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate, A new synthetic method of this compound is introduced below., Recommanded Product: Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate

To a solution of compound 3 (2.04 g, 0.01 mol) in ethanol (40 mL) hydrazine hydrate (0.50 g,0.01 mol) was added. The reaction mixture was heated under reflux for 6 h then poured ontoice/water mixture containing few drops of hydrochloric acid and the formed solid product wascollected by filtration. Brown crystals from ethanol; yield: 1.15 g (80%); m.p. > 300 oC. IR, :3488-3429 (NH2, NH), 3054 (CH aromatic), 2983 (CH2), 1684 (CO), 1640 (C=N), 1630 (C=C).1H-NMR: : 4.93 (s, 2H, CH2), 4.89 (s, 2H, NH2, D2O exchangeable), 7.29-7.39 (m, 4H, C6H4),8.28, 8.32 (2s, 2H, 2NH, D2O exchangeable). 13C NMR (DMSO): 52.8 (CH2), 120.3, 123.8,124.6, 126.4, 127.3, 129.8 (C6H4), 163.8 (CO), 173.4 (C=N); Anal. calcd for C9H10N4O: C,56.83; H, 5.30; N, 29.46%. Found: C, 56.66; H, 5.28; N, 29.69%. MS: m/z: (%) 190 (M+, 36%).

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:
Article; Mohareb, Rafat M.; Gamaan, Marwa S.; Bulletin of the Chemical Society of Ethiopia; vol. 32; 3; (2018); p. 541 – 557;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem