Tag: M.W=300-400

Some common heterocyclic compound, 2620-76-0, name is 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, molecular formula is C19H13BrN2, 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. SDS of cas: 2620-76-0

Example 1.3.3 1-phenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzo[d]imidazole (10): A mixture of Compound 9 (0.70 g, 2 mmol), bis(pinacolate)diborane (0.533 g, 2.1 mmol), 1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium (Pd(dppf)Cl2) (0.060 g, 0.08 mmol) and anhydrous potassium acetate (0.393 g, 4 mmol) in 1,4-dioxane (20 mL) was heated at 80 C. under argon overnight. After cooling to r.t., the whole mixture was diluted with ethyl acetate (80 mL) then filtered. The solution was absorbed on silica gel, then purified by column chromatography (hexanes/ethyl acetate 5:1 to 3:1) to give a white solid (Compound 10) (0.64 g, in 81% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2620-76-0, its application will become more common.

Reference:
Patent; Nitto Denko Corporation; US2012/15998; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 103057-10-9, These common heterocyclic compound, 103057-10-9, name is 4-(Chloromethyl)-1-trityl-1H-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.

EXAMPLE 1 STR49 To a solution of diisopropylamine (1.078 mL) in anhydrous THF (7 mL) was added n-butyllithium (3.08 mL; 2.5M) dropwise at 0 C. The resulting solution was stirred at 0 C. for 40 minutes and then was cooled to -23 C. To this mixture was added N-methyl-2-piperidinone (0.80 mL) (1.) the mixture was stirred at -23 C. for 0.5 hour, and then at -78 C. for 1 hour. To the above mixture was added dropwise a solution of 4-chloromethyl-N-trityl-imidazole (2.70 g) STR50 in anhydrous THF (14 mL). The mixture was stirred at -78 C. for 4 hours and then was allowed to warm up to room temperature slowly overnight (16 hours). Water and ethyl acetate were added to the mixture, the resulting mixture was shaken vigorously, the layers separated, and the aqueous layer was extracted with ethyl acetate several times. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated to give the crude product, which was purified by flash chromatography (1% to 2% of ammonia saturated methanol in CH2 Cl2) to give 2 (1.58 g; 52% yield).

The synthetic route of 103057-10-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Schering Corporation; US5807872; (1998); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 827320-59-2, name is 1-butylsulfonic-3-methylimidazolium hydrogensulfate, 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 827320-59-2, Formula: C8H16N2O7S2

Synthesis of 1-Sulfobutyl-3-methylimidazole Sulfate Ionic LiquidHydroxylamine Salts: Weigh the 1-sulfobutyl-3-methylimidazolium bisulfate ionic liquidobtained in the second step 5.06 (16.0 mmol) was placed in the reactor. 22.9 ml (32.0mmol of hydroxylamine) was added dropwise to the above ionic liquid in the first step,and the mixture was stirred at a low temperature (? 0 C) for 2 hours, The reactionsolution was evaporated at 70 C to give a white solid product 1-sulfobutyl-3-methylimidazole bisulfate ionic liquid type hydroxylamine salt. After the ionic liquidtype hydroxylamine salt was dried, Weighing 4.25 g, the yield was 69.5%.

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; Hebei University of Technology; WANG, YANJI; LI, ZHIHUI; ZHANG, DONGSHENG; QI, XUDONG; XU, YUANYUAN; YANG, QIUSHENG; ZHAO, XINQIANG; (7 pag.)CN104086474; (2016); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 33016-47-6,Some common heterocyclic compound, 33016-47-6, name is 1-Trityl-1H-imidazole-4-carbaldehyde, molecular formula is C23H18N2O, 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 solution of methyltriphenylphosphonium bromide (557mg, 1.56mmol) in THF (8mL) was added 1.0 M NaHMDS solution in THF (1.56mL, 1.56mmol) under argon at O0C. The mixture was stirred at this temperature for 30mins followed by the addition of 1-trityl-1H-imidazole-4-carbaldehyde (440mg, 1.3mmol). The reaction was stirred at O0C to room temperature for 3 hours, quenched with saturated aqueous NH4CI solution, extracted with ethyl acetate (3 x 3OmL). The combined organic layers were washed with water, brine, dried over magnesium sulfate, filtered, and concentrated under vacuum. The residue was purified by flash chromatography to give 1-trityl-4-vinyl-1H-imidazole (374 mg) with a yield of 86%.

The synthetic route of 33016-47-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; S BIO PTE LTD; WO2009/93981; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 1219741-21-5, These common heterocyclic compound, 1219741-21-5, name is 5-Chloro-6-iodo-1H-benzo[d]imidazole-2(3H)-thione, 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.

Cs2CO3 (2.3 g, 7.08 mmol), followed by tert-hutyl bromoacetate (0.52 mL, 3.54 mmol), was added to a solution of 5- chloro-6-iodo-l,3-dib.ydro-2H-benzimidazole-2~thione (Intermediate 7, 1.1 g, 3.54 mmol) in THF (20 mL) at O0C. The reaction was stirred at rt for 0.5 h. Volatiles were removed and the residue was partitioned between EtOAc and water. Concentration afforded the desired product as a white power. LC-MS: calculated for C13H14ClIN2O2S 423.95, observed m/e 424.8 (M+H)+.

Statistics shows that 5-Chloro-6-iodo-1H-benzo[d]imidazole-2(3H)-thione is playing an increasingly important role. we look forward to future research findings about 1219741-21-5.

Reference:
Patent; MERCK SHARP & DOHME CORP.; METABASIS THERAPEUTICS, INC.; DANG, Qun; CHUNG, De Michael; GIBSON, Tony, S.; JIANG, Hongjian; CASHION, Daniel, K.; BAO, Jianming; LAN, Ping; LU, Huagang; MAKARA, Gergely, M.; ROMERO, F. Anthony; SEBHAT, Iyassu; WODKA, Dariusz; WO2010/51206; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 33016-47-6, 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. 33016-47-6, name is 1-Trityl-1H-imidazole-4-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 34: Preparation of intermediate 8: 1-(1 -trityl-1 W-imidazol-4-yl)ethanolTo a solution of 1 -trityl-1 H-imidazole-4-carbaldehyde (10.0 g, 0.03 mol) in anhydrous THF (100 mL) was added dropwise methyl magnesium bromide (1.4 M in hexane, 52.8 mL, 0.075 mol) at O0C. After the addition, the mixture was stirred at RT overnight. The reaction was quenched with sat. aq. NH4CI (50 mL) and the mixture extracted with CH2CI2 (3*50 mL). The organic layers were combined, washed with 1 N aq. NaOH (3chi20 mL), water (3chi20 mL) and brine (100 mL), dried over MgSO4 and evaporated. The residue was purified via column chromatography {silica gel, EtOAc/Petroleum ether 1 :5) to yield the title compound (8.0 g, 75.0%) as a white solid.

The synthetic route of 1-Trityl-1H-imidazole-4-carbaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2008/4096; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 17464-88-9, 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. 17464-88-9 name is 1,3,4,6-Tetrakis(methoxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, 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.

60 g (0.188 mol) of tetramethoxymethylglycoluril (product name: POWDERLINK [registered trademark] 1174 commercially available from Japan Cytec Industries, hereinafter abbreviated as PL-LI in this specification), 1,200 g of propylene glycol monomethyl ether (hereinafter abbreviated as PGME in this specification), and 120 g of a washed ion-exchange resin for a catalyst (product name: AMBERLYST [registered trademark] 15JWET, commercially available from Dow Chemical Company, hereinafter abbreviated as 15JWET in this specification) were put into a 2,000 mL flask, and the mixture was stirred and dissolved at 25¡ã C. and then heated and stirred under a reduced pressure (80 Torr to 100 Torr) at 60¡ã C. for 7 hours. Then, the pressure inside the flask was recovered and cooling was performed to 25¡ã C., and then 15JWET was filtered off to obtain a desired compound (hereinafter abbreviated as PGME-PL in this specification). The obtained compound was identified by 1H NMR. As a result, it was confirmed that a peak (31.9 ppm) of a methoxy group of PL-LI disappeared and about 4 molecules of PGME were introduced into one molecule of PL-LI, and the glycoluril derivative of Formula (1A-1) (hereinafter abbreviated as PGME-PL in this specification) was obtained. [1.0 to 1.1 ppm (3H, ?CH3), 3.2 to 3.3 ppm (20H, ?OCH3 and ?CH2O?), 3.6 to 3.8 ppm (4H, ?OCH<)] At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3,4,6-Tetrakis(methoxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, and friends who are interested can also refer to it. Reference:
Patent; NISSAN CHEMICAL CORPORATION; SAKAIDA, Yasushi; TAKASE, Kenji; KISHIOKA, Takahiro; SAKAMOTO, Rikimaru; (14 pag.)US2019/163063; (2019); 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. 29914-81-6, name is 1,3-Bis(1H-benzo[d]imidazol-2-yl)benzene, A new synthetic method of this compound is introduced below., Formula: C20H14N4

General procedure: To 10 mL dry acetone were added [Ru(H2bip)Cl3] (54 mg,0.10 mmol) and AgOTf (96 mg, 0.37 mmol). The mixture wasrefluxed for 2 h before cooling to room temperature. The resultingAgCl precipitate was removed by filtration, and the filtrate wasconcentrated to dryness. To the residue were added ligand Mebib(36.9 mg, 0.11 mmol), DMF (10 mL), and t-BuOH (10 mL). Themixture was then refluxed for 24 h. After cooling to room temperature,the solventwas removed under reduced pressure, and theresiduewas dissolved in a mixture of 10 mL methanol and 1mL 1Maq. HCl. The mixture was then treated with 100 mg KPF6. Theresulting precipitate was collected by filtration and washing withwater and Et2O. The obtained solid was subjected to flash columnchromatography on silica gel (eluent: CH3CN/H2O/aq.KNO3, 100/10/0.2) to give 34.5 mg of 1(PF6)2 in 37% yield.

The synthetic route of 29914-81-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shao, Jiang-Yang; Zhong, Yu-Wu; Journal of Organometallic Chemistry; vol. 845; (2017); p. 144 – 150;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 760212-58-6,Some common heterocyclic compound, 760212-58-6, name is 1-(4-Bromophenyl)-2-phenyl-1H-benzo[d]imidazole, molecular formula is C19H13BrN2, 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.

In one 250 mL flask, 2.4 g (5.00 mmol) of Int.16, 1.9 g (5.50 mmol) of intermediate (13) 0.06 g (0.50 mmol) of Pd(PPh3)4, 0.7 g (12.5 mmol) of K2CO3, 50 mL of toluene, 25 mL of EtOH and 25 mL of H2O were mixed and then refluxed. After the reaction is complete, cool to room temperature and add 200 mL H2O. The mixture was extracted twice with 300 mL of dichloromethane (DCM), the extract was dried with Na2SO4, filtered and the filtrate was concentrated under reduced pressure. The solid was dissolved in chloroform and purified by silica gel column chromatography (dichloromethane (DCM) / ethyl acetate (EA)). Solidification with dichloromethane (DCM) / n-hex and filtration gave 1.3 g (yield: 43.3%) of compound 4-418 (WS16-30-067) as a beige solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(4-Bromophenyl)-2-phenyl-1H-benzo[d]imidazole, its application will become more common.

Reference:
Patent; Raepto Co., Ltd.; Kim Gyu-ri; Go Byeong-su; Kim Hye-jeong; Ryu Yong-jae; Im Cheol-su; Park Yong-pil; Yoon Jeong-hun; Han Gap-jong; Oh Yu-jin; (85 pag.)KR2017/142950; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 33016-47-6, These common heterocyclic compound, 33016-47-6, name is 1-Trityl-1H-imidazole-4-carbaldehyde, 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 solution of (4a/1?, 10bS)-1 ,2,3,4,4a,5,6,10b-octahydro-1 ,10-phenanthroline (0.25 g, 1.3 mmol), 1-(triphenylmethyl)-1 /-/-imidazole-4-carbaldehyde (similar methods as described in J. Org. Chem. 2002, 67, 620-624; 0.89 g, 2.6 mmol) , and acetic acid (0.078 g, 1.3 mmol) in 5 ml_ of 1 ,2-dichloroethane was added sodium triacetoxyborohydride (0.82 g, 3.9 mmol). The mixture was stirred at room temperature for 16 hours. The mixture was diluted with water and extracted 3 times with 10 mL of dichloromethane. The organic phase was concentrated and the residue purified by silica chromatography eluting with a 0% to 5% gradient of 2 M ammonia in methanol with dichlromethane as co-eluent to yield 0.27 g (41%) of (4afl,1 ObS)-I -{[1-(triphenylmethyl)-1 H-imidazol-4-yl]methyl}-1 ,2,3,4,4a,5,6,1 Ob- octahydro-1 ,10-phenanthroline. 1 H NMR (400 MHz, METHANOL-D4) delta ppm 1.6 (m, 5 H), 2.0 (m, 1 H), 2.3 (m, 2 H), 2.7 (m, 1 H), 2.9 (m, 1 H), 3.0 (m, 1 H), 3.4 (m, 2 H), 3.8 (m, 1 H), 6.8 (s, 1 H), 7.1 (m, 6 H), 7.2 (dd, J=U, 4.6 Hz, 1 H), 7.3 (s, 1 H), 7.3 (m, 9 H), 7.5 (d, J=8.1 Hz, 1 H), 8.2 (d, J=4.4 Hz, 1 H); MS m/z 511 (M+1).

The synthetic route of 33016-47-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/96444; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem