Month: February 2021

Related Products of 7189-69-7,Some common heterocyclic compound, 7189-69-7, name is 1,1′-Sulfonyldiimidazole, molecular formula is C6H6N4O2S, 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.

[0118] The following describes a preparation of compound 29. (0215) [0119] To prepare compound 29, a solution of n-butyllithium (2.50 M in hexanes, 84.0 mu., 0.21 mmol, 7.00 equiv) was added to a stirred solution of hexamethyldisilazane (49 mu,, 0.23 mmol, 7.7 equiv) in tetrahydrofuran (5 ml) at 0 C. The reaction mixture was briefly warmed to 23 C then was cooled to 0 C whereupon a solution of 28 (12 mg, 30 muetaiotaomicron, 1.0 equiv) in tetrahydrofuran (2 ml) was added. The resultant mixture was stirred at 0 C for 30 min, then was cooled to -10 C whereupon Nu,Nu’- sulfuryldiimidazole (54 mg, 0.27 mmol, 9.0 equiv) was added. The reaction mixture was warmed to 23 C and stirred at that temperature for 12 h. Excess Nu,Nu-sulfuryldiimidazole was quenched by the addition of methanol (5 ml), and the resultant mixture was concentrated. The residue was partitioned between saturated aqueous bicarbonate solution (20 ml) and dichloromethane (20 ml). The layers were separated and the aqueous phase was extracted with dichloromethane (3 x 25 mL). The combined organic layers were dried over anhydrous sodium sulfate and the dried solution was concentrated. The residue was purified by flash column chromatography (20% ethyl acetate-hexanes) to afford 29 (14 mg, 88%) as a colorless oil. Imidazole 29: TLC: 20% ethyl acetate-hexanes, Rf = 0.33 (UV, CAM). 1H NMR (500 MHz, CDC13) delta: 8.01 (s, 1H), 7.49- 7.47 (m, 3H), 7.39-7.35 (m, 4H), 7.22 (s, 1H), 6.06 (s, 1H), 5.16 (d, J = 10.5 Hz, 1H), 4.57 (dd, J = 1 1.0 Hz, J 4.5 Hz, 1H), 2.57 (s, 3H), 2.27-2.16 (m, 2H), 2.12-2.08 (dd, J = 14.5 Hz, J = 4.5 Hz, 1H), 2.04-1.94 (m, 2H), 1.89-1.83 (m, 1H), 1.76-1.67 (m, 3H), 1.23-122 (m, 1H), 1.19 (s, 3H), 0.95 (d, J = 7.0 Hz, 3H), 0.93 (d, J = 6.5 Hz, 3H), 0.92 (d, J = 7.0 Hz, 3H). 13C NMR (500 MHz, CDC13). delta: 165.2, 156.5, 142.0, 137.1, 131.6, 129.2, 128.5, 126.3, 1 17.9, 116.8, 90.5, 85.3, 81.1, 70.4, 48.8, 46.4, 35.7, 32.5, 31.1, 29.7, 24.0, 22.5, 18.1 , 17.4, 16.8. FTIR (NaCl, thin film), cm”1 2925, 2854, 1718, 1627, 1423, 1203, 1 158. HRMS: ESI [M + H]+ Calcd. for C28H37N206S: 529.2367. Found: 529.2346.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,1′-Sulfonyldiimidazole, its application will become more common.

Reference:
Patent; THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; UNIVERSITY OF HAWAII; CHAIN, William J.; BEUTLER, John A.; FASH, David; FIGG, William D.; LI, Zhenwu; PEER, Cody John; RAMOS, Joe William; SULZMAIER, Florian J.; WO2015/120140; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 15965-54-5, These common heterocyclic compound, 15965-54-5, name is 2-Chloro-5-methoxy-1H-benzo[d]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.

The substances listed in the table which follows are also prepared by the methods given above.

The synthetic route of 15965-54-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Aktiengesellschaft; US6387939; (2002); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 68282-53-1,Some common heterocyclic compound, 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, molecular formula is C5H6N2O, 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.

The compound (53.8 mg) obtained in Example 1-4 was dissolved in methanol (0.8 ml). Then, the solution was added with trimethyl orthoformate (50 mul), acetic acid (50 mul), and 4-methyl-5-imidazole carboxaldehyde (manufactured by Aldrich Corporation) (28.5 mg) and stirred at room temperature for 10 minutes. Subsequently, sodium cyanoborohydride (24.4 mg) was added, followed by stirring overnight at room temperature. The solvent was distilled off under reduced pressure and then the residue was dissolved in chloroform, followed by washing with 1 mol/l sodium hydroxide and saturated saline solution and drying with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure and the residue was then purified through silica gel column chromatography (chloroform/methanol) and then treated with hydrochloric acid, thereby obtaining hydrochloride (33.5 mg) of the subject compound as a white solid. MS(FAB,Pos.)m/z=480[M+H]+1H-NMR(500MHz,DMSO-d6):delta=0.81(6H,t,J=7.3Hz),1.32-1.43(6H,m),1.51(2H,quint.,J=7.1Hz),2.04(3H,br),2.28(4H,t,J=7 .1Hz),2.35(2H,t,J=7.1Hz),3.24(2H,dd,J=6.8,5.9Hz),3.31-3.47(2H,m),3.56(4H,br),6.85(1H,br),7.10(1H,br),7.47(2H,d,J=7 .8Hz),7.51(1H,s),7.78(2H,d,J=8.3Hz),8.40(1H,t,J=5.9Hz).

The synthetic route of 68282-53-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kureha Chemical Industry Co., Ltd.; EP1550657; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 7757-21-3, name is (1H-Benzo[d]imidazol-2-yl)methanamine hydrochloride, 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 7757-21-3, Computed Properties of C8H10ClN3

In a 100 mL three-necked flask, NaOH (15 g, 0.38 mol) and 15 mL of water were added, mechanically stirred, and after clearing, III-1 (2.63 g, 14.32 mmol) was added.Tetrabutylammonium bromide (185 mg, 0.57 mmol) was stirred at 25 C for 1 hour, and a solution of 1,2-dibromoethane (5.38 g, 28.64 mmol) dissolved in 50 mL of DMF was added dropwise.After the completion of the dropwise addition, the reaction was carried out at 25 C for 4 hours, and filtered by suction.Inorganic salt, concentrated under reduced pressure to give a white solid.Column chromatography (dichloromethane:methanol:aqueous ammonia = 50:1: 0.05 to 40:1:0.05) was purified to afford product (IV-1) 1.25 g, yield 50.4%.

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, (1H-Benzo[d]imidazol-2-yl)methanamine hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; China Pharmaceutical University; Zhu Qihua; Xu Yungen; Wang Junwei; Li Hui; Zhang Guangxia; Ge Yiran; Guan Zhe; (15 pag.)CN109251204; (2019); A;,
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. 39513-26-3, name is 5-Bromo-1,3-dihydrobenzoimidazol-2-one, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 5-Bromo-1,3-dihydrobenzoimidazol-2-one

EXAMPLE 9 5-(3-Nitro-phenyl)-1,3-dihydro-benzoimidazol-2-one Prepared from 5-bromo-1,3-dihydro-benzoimidazol-2-one and 3-nitro-phenyl boronic acid in the same fashion as that of Example 5. White solid: mp 324-325 C.; 1H-NMR (DMSO-d6) delta 10.8 (s, 2H), 8.4 (m, 1H), 8.15 (d, 1H, J=7.5 Hz), 8.1 (d, 1H, J=7.5 Hz), 7.7 (t, 1H, J=7.5 Hz), 7.35 (d, 1H, J=7.5 Hz), 7.3 (s, 1H), 7.05 (d, 1H), J=7.5 Hz); MS (ES) m/z 254 ([M-H]-, 100%); Anal. Calc. For C13H9N3O3: C, 61.18, H, 3.55, N, 16.46. Found: C, 60.5, H, 3.69 N, 15.53.

According to the analysis of related databases, 39513-26-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; American Home Products Corporation; Ligand Pharmaceutical, Inc.; US6423699; (2002); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 3034-50-2, 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. 3034-50-2, name is Imidazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows.

l,4-Diazabicyclo[2.2.2]octane (21 g, 187.33 mmol) and dimethyl sulfamoyl chloride (18.4 mL, 171.72 mmol) were added to a stirred suspension of lH-imidazole-4- carbaldehyde (15 g, 156.11 mmol) in acetonitrile (300 mL) at 0 C. The mixture was allowed to warm to room temperature and stirred for 18 hours. The mixture was concentrated in vacuo and the residue was diluted with water and extracted withEtOAc. The organic layer was separated, dried (MgS04), filtered and the solvent was evaporated in vacuo. The crude product was purified by flash column chromatography (silica; EtOAc in DCM 0/100 to 60/40). The desired fractions were collected and concentrated in vacuo to yield 4-formyl-N,N-dimethyl-lH-imidazole-l -sulfonamide (27.2 g, 86 % yield) as a cream solid.

The chemical industry reduces the impact on the environment during synthesis Imidazole-4-carbaldehyde. I believe this compound will play a more active role in future production and life.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; TRABANCO-SUAREZ, Andres, Avelino; DELGADO-JIMENEZ, Francisca; VEGA RAMIRO, Juan, Antonio; TRESADERN, Gary, John; GIJSEN, Henricus, Jacobus, Maria; OEHLRICH, Daniel; WO2012/85038; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 53484-18-7, 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. 53484-18-7, name is 1-Methyl-1H-benzo[d]imidazole-6-carboxylic acid belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of CDI (1.2 equiv) and the proper carboxylic acid in anhydrous solvent under a N2 atmosphere, was stirred at 40-50 C for 3 h. The solution was then cooled at room temperature and 2-amino-5-nitrothiazole and in some cases 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), was added. The mixture was heated at 60 C for 12-18 h, cooled at room temperature and water was added to precipitate the hybrid compounds. The solid was filtered and washed with acetone and water for give the corresponding hybrid compounds.

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-Methyl-1H-benzo[d]imidazole-6-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Soria-Arteche, Olivia; Hernandez-Campos, Alicia; Yepez-Mulia, Lilian; Trejo-Soto, Pedro Josue; Hernandez-Luis, Francisco; Gres-Molina, Jorge; Maldonado, Luis A.; Castillo, Rafael; Bioorganic and Medicinal Chemistry Letters; vol. 23; 24; (2013); p. 6838 – 6841;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 570-22-9, name is 1H-Imidazole-4,5-dicarboxylic acid, 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 570-22-9, Safety of 1H-Imidazole-4,5-dicarboxylic acid

H3IMDC ligand (0.1500 g, 0.961 mmol) was dissolved in a baker with 30mL of deionizated water and 3.45 mL of NaOH dissolution (0.276 mol L-1) and left stirring in a round bottom flask. Then, when all the ligand was dissolved, 0.4548 g of Co(hfacac)2 (0.952 mmol) previously disolved in 10 mL of absolute ethanol was added. A pale orange suspension was formed which was left stirring for 3 hours and filtered under vacuum using a porous glass filter. The solid was washed first with 10 mL cool water and 15 mL of cool ethanol and then dried overnight at 70C. Yield: 182 mg (0.449 mmol, 47%)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-Imidazole-4,5-dicarboxylic acid, and friends who are interested can also refer to it.

Reference:
Article; Arrue, Ramon; Toledo, Dominique; Pena, Octavio; Pivan, Jean-Yves; Reis, Mario; Moreno, Yanko; Journal of the Chilean Chemical Society; vol. 63; 2; (2018); p. 4006 – 4011;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 104619-51-4,Some common heterocyclic compound, 104619-51-4, name is Di(1H-imidazol-1-yl)methanimine, molecular formula is C7H7N5, 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 2S: r4-(5-Amno- M .3.41 oxadiazol-2-vO-pyridin-3-ylH2-fluoro-4-methoxy- phenvD-amine; To a solution of 3-(2-Fluoro-4-methoxy-phenylamino)-isonicotinic acid hydrazide (150mg, 0.54mmol, 1eq) in DMSO (2ml_) C- (Di-imidazol-i-yl)-methyleneamine (175mg, 1.09mmol, 2eq) was added. The reaction mixture was stirred at RT under argon overnight and then poured into water. The product was isolated by filtration (89 mg). LC/MS (Method A) [0.52mi?; 302(M+1)]

The synthetic route of 104619-51-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; APPLIED RESEARCH SYSTEMS ARS HOLDING N.V.; WO2007/123936; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 71759-89-2, name is 5-Iodo-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 71759-89-2, category: imidazoles-derivatives

4-Iodo-1H-imidazole (1 g, 5.2 mmol) and N,N-diisopropylethylamine (1.34 g, 10.4 mmol) wereadded to dry dimethylformamide (20 mL), and 1-(bromomethyl)-4-(trifluoromethyl)benzene (1.48 g,6.2 mmol) was added to reaction mixture at 20 C. After the reaction mixture was stirred at 20 Cuntil the starting material disappeared in thin layer chromatography (TLC), the reaction mixture was distilled in vacuo, dichloromethane (50 mL) was added to the mixture. The organic extract was washed twice with saturated aqueous NaHCO3 and NaCl (20 mL) respectively, and the organic extract was dried over Na2SO4. After solvent was removed under vacuum, the unpurified product was added to the next step directly.

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; Wen, Hui; Liu, Yuke; Wang, Shufang; Wang, Ting; Zhang, Gang; Chen, Xiaoguang; Li, Yan; Cui, Huaqing; Lai, Fangfang; Sheng, Li; Molecules; vol. 24; 11; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem