Author: Jessica.F

Application of 75370-65-9, 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. 75370-65-9, name is 4-Amino-1H-benzo[d]imidazol-2(3H)-one belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Preparation of 1-(4-chloro-2-(pyrrolidin-1-yl)benzyl)-3-(2,3-dihydro-2-oxo-1H-benzo[d]imidazol-4-yl)urea Amine 2ag (1g, 4.76mmol) was dissolved in 20 ml of AcOEt and at 0C triphosgene (1.4 g, lequiv.) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 10 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10ml) of compound 1a (700 mg, 4.9 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt). The solvent was evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1 X 20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 360 mg of a white solid. Yield = 19% 1HNMR (DMSO, 200 MHz) delta 1.89 (4H, m), 3.17 (4H, m), 4.30 (2H, d, J = 5.4 Hz), 6.61 (1H, dd, J = 7.6 Hz, J’ = 1 Hz), 6.69 (1H, t), 6.87 (4H, m), 7.24 (1H, d, J = 7.8 Hz), 8.38 (1H, bs), 10.00 (1H, bs), 10.59 (1H, bs); [M+1] 386.7 (C19H20ClN5O2 requires 385.85).

The synthetic route of 4-Amino-1H-benzo[d]imidazol-2(3H)-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pharmeste S.r.l.; EP2377850; (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. 1544-75-8, name is 5-Fluoro-1H-benzo[d]imidazol-2(3H)-one, A new synthetic method of this compound is introduced below., Recommanded Product: 1544-75-8

A solution of 5-fluoro-1 H-benzo[d]imidazol-2(3H)-one (16.0 g, 105 mmol) in DMF (400 mL) under nitrogen was cooled with an ice-bath, using a mechanical stirrer for agitation. It was then treated over 10 min with sodium hydride (60% w/w in mineral oil, 13.1 g, 327 mmol) and the resulting mixture was stirred at this temperature for 30 min before being treated with iodomethane (26.3 mL, 422 mmol) over 30 min. The resulting mixture was then allowed to warm to room temperature and after 1 h was carefully treated with water (500 mL). The aqueous phase was extracted with EtOAc (3 x 800 mL) and the combined organics were washed with brine (1 L), dried over MgS04 and concentrated in vacuo. Purification of the brown residue by flash chromatography on silica gel (SP4, 1.5 kg column, gradient: 0 to 25% (3: 1 EtOAc/EtOH) in cyclohexane) gave the title compound (15.4 g, 86 mmol, 81 %) as a pink solid. LCMS (high pH): Rt 0.76 min; [M+H+]+ = 181.1 deltaEta NMR (400 MHz, CDCI3) ppm 6.86-6.76 (m, 2H), 6.71 (dd, J = 8.3, 2.3 Hz, 1 H), 3.39 (s, 3H), 3.38 (s, 3H).

The synthetic route of 1544-75-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; BAMBOROUGH, Paul; CHUNG, Chun-Wa; LE GALL, Armelle; SHEPPARD, Robert John; (36 pag.)WO2016/62737; (2016); 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. 496-46-8, name is Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C4H6N4O2

EXAMPLE 8; PREPARATIONOFA LINEAR CUCURBITURIL TRIMER; In another exemplary pathway for preparing a linear cucurbituril trimer, disubstituted cucurbiturils are prepared and are thereafter attached to an assembling unit, as is presented in Figure 24. As an exemplary starting material, a”benzil trimer” (Figure 24, Compound 39) is reacted with urea in a 1: 6 ratio, in benzene and trifluoroacetic acid, so as to afford a benzil-derived structure having three glycoluril units attached thereto. The latter is further substituted at each end with a carboxyl group, which can be used for further attachment of a variety of functional moieties or for forming cucurbituril assemblies. Thus, the benzil-derived glycoluril structure is reacted with glycoluril, Compound 2, in a 1: 15 ratio, and with formaldehyde, in the presence of concentrated sulfuric acid, to thereby form a linear, derivatized, cucurbituril trimer (Figure 24, Compound 40)

According to the analysis of related databases, 496-46-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TECHNION RESEARCH & DEVELOPMENT FOUNDATION LTD.; WO2005/23816; (2005); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 492-98-8, 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. 492-98-8, name is 1H,1’H-2,2′-Biimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A mixture of Na2MoO4*2H2O (0.0718 g, 0.296 mmol), 2,2′-biimidazole (biim, 0.0430 g, 0.257 mmol), NiF2*4H2O (0.0095 g, 0.056 mmol), and Na2SiO3*9H2O (0.0708 g, 0.249 mmol) in H2O (10 mL) was adjusted to pH 2.5 with HCl (1.0 mol/L solution in water) and heated at 150 C for 48 h in a sealed 25 mL teflon-lined stainless vessels under autogenous pressure. After cooling to ambient temperature with 800 min, black block crystals (yield50%, based on Na2MoO4*2H2O) were obtained.

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,1’H-2,2′-Biimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Wang, Hao; Chen, Yi-Ping; You, Zhu-Chai; Zhou, Meng-Xi; Zhang, Ning; Sun, Yan-Qiong; Chinese Chemical Letters; vol. 26; 2; (2015); p. 187 – 192;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 288-32-4, 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. 288-32-4, name is 1H-Imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Under nitrogen, imidazole was dissolved in anhydrous THF, and an appropriate amount of acetic anhydride was dropped slowly into the solution; then reaction was carried out for about half an hour accompanied by exothermic phenomena. After the reaction was completed, the solvent was removed by vacuum reduced pressure concentration to generate a solid product. Then, the obtained solid was rinsed with n-hexane and filtered to provide compound 11 as white solid, with yield of about 98percent.

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

Reference:
Patent; Eternal Chemical Co., Ltd.; Cheng, Pi-Jen; Chou, Meng-Yen; Lee, Chuan Zong; Wu, Chung-Jen; US2013/172569; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 939-70-8, name is 1-(1H-Benzo[d]imidazol-2-yl)ethanone, molecular formula is C9H8N2O, 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. Product Details of 939-70-8

General procedure: A 10%solution of NaOH (5 ml) in EtOH was added to a solutionof 2-acetylbenzimidazole (4) (1.6 g, 0.01 mol) in absoluteEtOH (20 ml) at 0C with stirring. Then the solution of anaromatic aldehyde (0.01 mol) in absolute EtOH (10 ml)was added dropwise. The reaction mixture was stirred for12 h at room temperature. After completion of reaction(monitored by TLC), the reaction mixture was poured ontocrushed ice. The separated solid was filtered off, washedwith water, and dried. The residue was purified by columnchromatography (silica gel, eluent 10% ethyl acetate inpetroleum ether) to afford pure benzimidazole-derived chalcone 5a-m.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 939-70-8, its application will become more common.

Reference:
Article; Meshram, Gangadhar A.; Vala, Vipul A.; Chemistry of Heterocyclic Compounds; vol. 51; 1; (2015); p. 44 – 50; Khim. Geterotsikl. Soedin.; vol. 51; 1; (2015); p. 44 – 50,7;,
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 40197-20-4 as follows. Application In Synthesis of 5-Bromo-1H-benzo[d]imidazole-2-carboxylic acid

Preparation Example 1 N-[3-(dimethylamino)propyl]-N’-ethylcarbodiimide hydrochloride (1.2 g) was added to a mixture of 5-bromo-1H-benzimidazol-2-carboxylic acid (1.0 g), 1-[4-(trifluoromethyl)benzyl]piperazine (1.0 g), 1H-benzotriazol-1-ol (840 mg), and N,N-dimethylformamide (10 ml: hereinafter, abbreviated as DMF), followed by stirring at room temperature overnight. A saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, followed by stirring at room temperature for 1 hour, and the resulting solid was collected by filtration, followed by drying under reduced pressure. The obtained solid was dissolved in a mixture of chloroform (100 ml) and ethanol (1 ml) while heating to reflux. The mixture was cooled to room temperature and then hexane (100 ml) was added thereto. The resulting solid was collected by filtration, followed by drying under reduced pressure, thereby obtaining (5-bromo-1H-benzimidazol-2-yl){4-[4-(trifluoromethyl)benzyl]piperazin-1-yl}methanone (1.4 g) as a solid.

According to the analysis of related databases, 40197-20-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Astellas Pharma Inc.; NAGASHIMA, Takeyuki; (31 pag.)EP3231426; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 53484-17-6, 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. 53484-17-6 name is 1-Methyl-1H-benzo[d]imidazole-5-carboxylic acid, 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.

To a stirred solution acid compound 172 (6.7 g, 38.06 mmol) and N,O- dimethylhydroxylamine (5.57 g, 57.09 mmol) in DCM (70 mL) at 0 oC was added DIPEA (13.53 mL, 76.13 mmol), stirred for 15 min, followed by addition of HATU (21.69 g, 57.09 mmol), again stirred for 15 min. The reaction mixture was then stirred at room temperature for overnight. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was diluted with ice cold water and extracted with DCM. The combined organic layers were dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford a crude compound. The crude compound was purified by silica gel column chromatography using 2% MeOH/DCM to afford the title compound 173 (8.1 g, 98.78%) as a brown liquid. TLC: 5% MeOH/DCM (Rf: 0.3). 1H LCMS Calculated for C11H13N3O2: 219.10; LCMS observed: 219.95 (M+1)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Methyl-1H-benzo[d]imidazole-5-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; ASSEMBLY BIOSCIENCES, INC.; TURNER, William, W., Jr.; LI, Leping; HAYDAR, Simon, Nicolas; BURES, Mark, G.; RAI, Roopa; FRANCIS, Samson; ARNOLD, Lee, Daniel; (0 pag.)WO2018/160878; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 1402838-08-7, name is 2-(1-Trityl-4-imidazolyl)benzaldehyde, molecular formula is C29H22N2O, 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. category: imidazoles-derivatives

A slurry of tert-butyl 2?-oxospiro[8-azabicyclo[3 .2.1 ]octane-3, I ?-cyclobutanej-8-carhoxylate (2.65 g, 9.98 .mmol), 2-[ 1.-(triphenylmethyl)- IH-imidazol-4-yl.]benzaldehyde (4.55 g,11.0 mmol) and Ca(OH)2 (1.48 g, 20.0 mmol) in EtOH (33 mL) was stirred for 24 h at 80 C.The reaction was cooled to room temperature and insoluble material was removed by filtration. The filtrate was concentrated. The residue was purified by a silica gel column eluting withDCM/methanoj. (90:10) to afford 5.60 g (85%) tertbutyl E)-2?-oxo-3?(2-(1-trity1-1Wirnidazo1.-4-yl)benzylidene)-8-azaspiro[bicyclo{3 .2.1 ]octane-3, 1 ?-cyclobutane]-S-carboxylate as a pale yellow solid. LCM.S (ESI) m/z 662.3 [M+F1]4.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1402838-08-7, its application will become more common.

Reference:
Patent; GENENTECH, INC.; PEI, Zhonghua; PASTOR, Richard; GAZZARD, Lewis; PARR, Brendan; LIU, Wendy; MENDONCA, Rohan; WU, Guosheng; YUEN, Po-Wai; (183 pag.)WO2019/5559; (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 6232-91-3 as follows. SDS of cas: 6232-91-3

2-Amino-5-methoxy-1H-benzimidazole was obtained from 4-methoxybenzene-1,2-diamine following the reported operation. 17 To a solution of N-carbobenzyloxy-l-proline (2.49 g, 10.0 mmol, 1.0 equiv) and 2-amino-5-methoxy-1H-benzo[d]imidazole (1.79 g, 11.0 mmol, 1.1 equiv) in CH2Cl2 (30.0 mL) N,N’-dicyclo-hexylcarbodiimide (2.26 g, 11.0 mmol, 1.1 equiv) and 4-dimethylamino pyridine (1.34 g, 11.0 mmol, 1.1 equiv) were added at 0 ¡ãC under N2 atmosphere. The reaction mixture was stirred for 30 min at 0 ¡ãC, then at room temperature for 24 h. The reaction mixture was filtrated through silica gel pad (SiO2 15 g) to remove dicyclohexylurea. Further purification was through flash column chromatography (Methanol/DCM=1:10). 1H NMR (400 MHz, CHCl3-d): delta 7.50-7.30 (4H, m), 7.20-6.80 (4H, m), 5.15-5.05 (2H, m), 4.60-4.40 (1H, m), 3.84 (3H, d, J=7.80 Hz), 3.72-3.48 (2H, m), 2.38-2.20 (1H, m), 2.10-1.75 (3H, m). 13C NMR (400 MHz, CHCl3-d): delta 179.3, 156.6, 154.5, 146.6, 136.7, 128.3, 128.0, 127.7, 127.4, 111.9, 66.5, 59.4, 55.7, 46.8, 30.8, 23.3. HRMS (ESI): m/z [M+H+] calcd for C21H23N4O4 395.1719, found 395.1714.

According to the analysis of related databases, 6232-91-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Tang, Gongkun; Guen, Uemit; Altenbach, Hans-Josef; Tetrahedron; vol. 68; 49; (2012); p. 10230 – 10235,6;; ; Article; Tang, Gongkun; Guen, Uemit; Altenbach, Hans-Josef; Tetrahedron; vol. 68; 49; (2012); p. 10230 – 10235;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem