Month: March 2021

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. 15965-31-8, name is 5-Chloro-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Safety of 5-Chloro-1H-imidazole

To a stirred mixture of intermediate E(3) (4.0 g, 11.1 mmol), KOH (0.93 g, 16.6 mmol) in DMSO (30 mL) was added chloroimmidazole (1.69 g, 16.6 mmol) at room temperature. The reaction mixture was stirred at 90 C for 18 h while monitoring by LC-MS and TLC. The reaction mixture was poured into crushed ice (50 g) and extracted with ethyl acetate (3 x 200 mL). The organic layer was washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure. The crude compound was purified by column chromatography (60-120 mesh silica) using 60-70% ethyl acetate in pet-ether to give tert-butyl 2-(2-(2-(4-chloro-lH-imidazol-l-yl)-5- nitrophenoxy)ethoxy)ethylcarbamate ( 3.0 g, 63.29%) as a yellow solid. LC-MS (M- 100)+ = 326.2. 1H NMR (400 MHz, CDC13) delta ppm 8.01-7.97 (2H, m), 7.88 (1H, s), 7.46- 7.44 (1H, d, J=8.8 Hz), 7.28-7.27 (1H, m), 4.92 (1H, s), 4.34-4.33 (2H, m), 3.86-3.83 (2H, m), 3.59-3.57 (2H, t, J=5.2 Hz), 3.37-3.34 (2H, m), 1.43 (9H, s).

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 15965-31-8.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BOY, Kenneth M.; GUERNON, Jason M.; MACOR, John E.; THOMPSON III, Lorin A.; WU, Yong-Jin; ZHANG, Yunhui; WO2012/9309; (2012); A1;,
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. 45676-04-8, name is 1-tert-Butylimidazole, A new synthetic method of this compound is introduced below., Product Details of 45676-04-8

THF (200 ml) and 1-tert-butylimidazole (12.42 g, 0.1 mol) were added into a 500 ml reactor containing a stirrer with N2 fully charged. After stirring evenly, the solution was cooled to -45 C. A solution of n-butyl lithium hexane (41.6 ml, 2.4 mol/L) was extracted with a 100 mL syringe and added slowly to the solution above while string. After stirring at -45 C. for 1 hour, the solution was raised to room temperature and kept stirring for 1 hour. Then, the solvent was removed by vacuum, and hexane (100 ml) was added in. 12.08 g (0.098 mol, 92.8%) product was obtained by remove the volatile components in vacuum after dispersion and filtration.

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; Tianjin University of Science&Technology; Jiang, Tao; Chen, Yanhui; Zhang, Le; Alam, Fakhre; Shao, Huaiqi; Li, Jian; Yan, Bing; (9 pag.)US2019/106366; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 10111-08-7, 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. 10111-08-7 name is Imidazole-2-carboxaldehyde, 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.

General procedure: To a solution of 1H-imidazole-2-carbldehyde (13 mmol) and potassium carbonate (16 mmol) in DMF (13 mL) was added alkyl bromide (16 mmol), and the reaction mixture was stirred at 50 C for 6 h. The inorganic solids were removed by filtration, and the filtrate was diluted with water and extracted with diethyl ether. The combined organic extracts were dried over anhydrous magnesium sulfate, and the volatile components were evaporated under vacuum to give the respective product.

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

Reference:
Article; Samaan, Nawras; Zhong, Qiu; Fernandez, Jayjoel; Chen, Guanglin; Hussain, Ali M.; Zheng, Shilong; Wang, Guangdi; Chen, Qiao-Hong; European Journal of Medicinal Chemistry; vol. 75; (2014); p. 123 – 131;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 1849-02-1, 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. 1849-02-1, name is 2-Chloro-1-methyl-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step 2 0.43 g (5.0 mmol) of piperazine and 0.24 g (1.0 mmol) of the compound obtained in Step 1 were placed in a dried round flask provided with nitrogen gas, followed by reacting the mixture at 150C for 30 mins. After cooling to room temperature, the reaction mixture was acidified with IN-HCl solution and washed with dichloromethane. The water layer was treated with IN-NaOH solution and extracted with dichloromethane. The formed organic layer was dried over anhydrous magnesium sulfate and concentrated under a reduced pressure, and the resulting residue was subjected to silica gel column chromatography (dichloromethaneimethanol^il) to obtain 0.15 g of l-methyl-2-(piperazin-l-yl)-benzoimidazole (yield: 69%).

The synthetic route of 2-Chloro-1-methyl-1H-benzo[d]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; CHEMON INC.; WO2008/153325; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 152628-03-0, 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 152628-03-0 as follows.

Example 2; Variant 2; Methanesulphonic acid is heated to about 80 C. At a temperature of 75 C. to 85 C., 2-propyl-4-methyl-1H-benzimidazole-6-carboxylic acid is added. Then at 85 C. to 95 C. N-methyl-o-phenylene-diamine is added.The mixture is heated to110 C. to 130 C. and phosphorus pentoxide is metered in until an internal temperature of not more than 160 C. is reached. Then the mixture is stirred for 3 hours at a maximum temperature of 145 C. It is cooled to <100 C. and water is metered into the reaction mixture. 50% sodium hydroxide solution is added at <100 C. until a pH of less than 3 is obtained.Finally, treatments with charcoal are carried out at <100 C.At a temperature of <80 C. isopropanol is added and the mixture is adjusted with sodium hydroxide solution to a pH between 4.5 and 7. The aqueous phase is separated off. In order to precipitate dimethyl-2'-propyl-2,5'-bi-1H-benzimidazole water is metered in, the contents of the apparatus are cooled to at least 40 C. for technical reasons and the product is isolated.Yield: 78-90% of theoryHPLC purity: >99.5%.

According to the analysis of related databases, 152628-03-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2011/190508; (2011); A1;,
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. 89830-98-8, name is 5-Cyclopropyl-1H-imidazole, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H8N2

[00641] A mixture of Example 134b (100 mg, 0.235 mmol), Example 134c (108 mg, 1.0 mmol), K2C03 (162 mg, 1.175 mmol), Cul (11 mg, 0.058 mmol) in dry DMSO (2 mL) was heated at 125¡ãC for 24 h. The reaction was cooled to r.t., and water (25 mL) was added. The resulting mixture was stirred for 5 min, and filtered to give the crude product, which was purified by prep-HPLC (by Ultimate XB-C18, 50 x 250 mm, 10 muetaiota, speed: 80 mL/min, eluent: A/B = H20/CH3C = from 75/25 to 45/55 over 30 min. Ret. Time =: 24.94 min), followed by prep-TLC (DCM/MeOH = 10/1) to give the desired product Example 134 (1.2 mg, yield 1percent) as a white solid. LC-MS [M+l]+ = 454.0. NMR (400 MHz, Chloroform-d) delta 11.80 (s, 1H), 8.23-8.15 (m, 3H), 8.04 (s, 1H), 7.97 (t, J= 7.9 Hz, 1H), 7.83 (s, 1H), 7.50 (s, 2H), 7.12 (s, 1H), 4.83 (t, J= 8.9 Hz, 1H), 4.58 (s, 2H), 4.41 (t, J= 6.9 Hz, 1H), 3.81 (s, 2H), 2.88 (s, 2H), 1.96 (d, J= 38.7 Hz, 1H), 0.89 (d, J= 7.0 Hz, 2H), 0.83 (s, 2H).

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; FRONTHERA U.S. PHARMACEUTICALS LLC; JIN, Bohan; DONG, Qing; HUNG, Gene; (214 pag.)WO2019/51265; (2019); 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 85330-50-3 as follows. Application In Synthesis of 4-Nitro-1H-benzo[d]imidazol-2(3H)-one

b)Preparation of 4-amino-benzimidazolin-2-one To a solution of 4-nitro-benzimidazolin-2-one (700 mg, 3.9mmol) in methanol(50 ml) and acetic acid (10 ml) was added 10% Pd/C (200 mg). The mixture was flushed with argon, then hydrogen was bubbled through the solution for 10 ain. and a hydrogen atmosphere was maintained at balloon pressure overnight. The mixture was filtered through celite and the celite was washed with methanol. The solvent was evaporated and chromatography of the resulting solid on silica gel (10%MeOH/CH2C2) gave the desired product (500 mg, 86%). 1H NMR (CD3SO2CD3): delta10.34 (s, 1H), 10.01 (s, 1H), 6.66 (t, 1H), 6.24 (d,1H), 6.22 (d, 1H), 5.15 (bs, 2H).

According to the analysis of related databases, 85330-50-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SmithKline Beecham Corporation; US6300325; (2001); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 38993-84-9,Some common heterocyclic compound, 38993-84-9, name is (1-Methyl-1H-imidazol-5-yl)methanol, molecular formula is C5H8N2O, 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.

Thionyl chloride (3.88mL, 53.5mmol) was added dropwise to 3-methyl-3H-imidazol-4- yl)-methanol (o.3g, 2.68mmol). The reaction was sonicated briefly, treated with DMF (1 drop) and allowed to stir at ambident temperature for 1 h. The volatiles were removed and the residue treated with diethyl ether. The diethyl ether was decanted and the procedure repeated 3 times. The semi-solid residue was treated with dimethylamine in THF (6.69mL, 13.38mmol) followed DMF (1 mL). The reaction was heated in a CEM microwave reactor at 8O0C for 30 minutes, treated with acetic acid (1 ml_) and purified by SCX cartridge to give the title compound (0.18g, 1.22mmol). LC-MS (method 1): R, 2.9 min, m/z 140 [MH]+.

The synthetic route of 38993-84-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARGENTA DISCOVERY LIMITED; ASTRAZENECA AB; WO2008/23157; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1615-14-1,Some common heterocyclic compound, 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol, molecular formula is C5H8N2O, 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.

Diethyl azodicarboxylate (435 mg, 2.5 mmol) was added dropwise to a suspension of 7-hydroxy-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin4-one (612 mg, 2 mmol), 2-(imidazol-1-yl)ethanol (280 mg, 2.5 mmol), (J. Med. Chem. 1993, 25 4052-4060), and triphenylphosphine (655 mg, 2.5 mmol) in methylene chloride (10 ml) at 5 C. The mixture was stirred for 10 minutes at 5 C. and then 1 hour at ambient temperature. The mixture was poured directly on to a silica column and eluted with methylene chloride/methanol (95/5) to give 7-(2-(imidazol-1-yl)ethoxy)-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (640 mg, 80%). 1H NMR Spectrum: (CDCl3) 1.19(s, 9H); 3.98(s, 3H); 4.34(m, 2H); 4.45(m, 2H); 5.94(s, 1H); 7.02(s, 1H); 7.07(s, 1H); 7.11(s, 1H); 7.64(s, 1H); 7.67(s, 1H); 8.17(s, 1H). MS-ESI: 423 [MNa]+

The synthetic route of 1615-14-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zeneca Limited; US6265411; (2001); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 137049-00-4, name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, molecular formula is C4H5ClN2O2S, 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. Recommanded Product: 1-Methyl-1H-imidazole-4-sulfonyl chloride

2.2 Ethyl 1-(3,4-dichlorobenzyl)-7-(2-(1-methyl-1 H-imidazole-4-sulfonamido)ethoxy)- 1 ,2,3,4-tetrahydronaphthalen-2-ylcarbamate; Ethyl 7-(2-aminoethoxy)-1 -(3,4-dichlorobenzyl)-1 ,2,3,4-tetrahydronaphthalen-2- ylcarbamate hydrochloride (100 mg, 0.229 mmol) and DMAP (27.9 mg, 0.229 mmol) were dissolved in CH2CI2 (15 ml) and 1-methyl-1 H-imidazole-4-sulfonyl chloride (41.3 mg, 0.229 mmol) dissolved in CH2CI2 (15 ml) was added. The reaction mixture was stirred over night at RT. After addition of H2O the phases were separated and the aqueous phase was extracted with CH2CI2. The organic layer was washed with HCI (1 N), NaHCO3 solution and NaCI solution, then dried on MgSO4 and the solvent was removed. To the residue EtOAc/ diethylether (1 :1 ) was added, stirred, and the precipitate was separated by filtration to obtain a brown solid of product (100 mg). ESI-MS [M+H+] = 581.5 Calculated for C26H30CI2N4O5S = 580.13

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 137049-00-4, its application will become more common.

Reference:
Patent; ABBOTT GMBH &amp;; CO. KG; AMBERG, Wilhelm; OCHSE, Michael; LANGE, Udo; KLING, Andreas; BEHL, Berthold; HORNBERGER, Wilfried; MEZLER, Mario; HUTCHINS, Charles; WO2010/92180; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem