Month: September 2021

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 288-32-4 as follows. Formula: C3H4N2

General procedure: Briefly, a mixture of imidazole (100 mmol), alkyl bromide (100 mmol) and K2CO3 (200 mmol) inacetone (200 mL) was refluxed overnight. Upon filtration and solvent removal, the remaining residuewas subjected to flash chromatography with ethyl acetate to produce >90percent yield.

According to the analysis of related databases, 288-32-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Doria, Oscar Forero; Castro, Ricardo; Gutierrez, Margarita; Valenzuela, Diego Gonzalez; Santos, Leonardo; Ramirez, David; Guzman, Luis; Molecules; vol. 23; 9; (2018);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 570-22-9,Some common heterocyclic compound, 570-22-9, name is 1H-Imidazole-4,5-dicarboxylic acid, molecular formula is C5H4N2O4, 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.

General procedure: 10 mL ethanol solution of 2.0 mmol metal salt was added into 10 mL ethanol solution of 2.0 mmol 4,5-imidazole dicarboxylic acid. Having blended the mixture under reflux for 1 h, methanol solution of 1.0 mmol NaOH was put into hot mixture drop by drop. After 5 h under reflux, solvent of the solution was removed, precipitate was filtered. The precipitates were washed with methanol 3 times and dried in 105 C. Molecular structures of complexes obtained from the reaction of 4,5-imidazole dicarboxylic acid ligand with metal salts were summarized in Fig. 2.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1H-Imidazole-4,5-dicarboxylic acid, its application will become more common.

Reference:
Article; Erdem, Ozlem; Yildiz, Emel; Inorganica Chimica Acta; vol. 438; (2015); p. 1 – 4;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

614-97-1, name is 5-Methyl-1H-benzo[d]imidazole, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Formula: C8H8N2

General procedure: A sealable reaction tube equipped with a magnetic stirrer barwas charged with 5,6-dimethyl-1H-benzo[d]imidazole (0.50 mmol,73 mg), benzaldehyde (1.0 mmol, 106 mg), di-tert-butyl-peroxide(1.0 mmol, 146 mg), 4 A molecular sieves (50 mg) and ethyl acetate(3.0 mL). The rubber septum was then replaced by a Teflon-coatedscrew cap, then the reaction must be under N2 and the reactionvessel placed in an oil bath at 110 C. After stirring the mixture atthis temperature for 15 h, it was cooled to room temperature anddiluted with ethyl acetate then washed with 0.5 mmol/L NaOHaqueous solution (5.0 mL3), dried over by MgSO4. After the solventwas removed under reduced pressure, the residue was purifiedby column chromatography on silica gel (hexane/EtOAc, 4:1 to6:1) to afford the desired product (5,6-dimethyl-1H-benzo[d]imidazol-1-yl)(phenyl)methanone (3a, 116 mg, 93% yield).

The synthetic route of 614-97-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yu, Lin; Wang, Min; Wang, Lei; Tetrahedron; vol. 70; 35; (2014); p. 5391 – 5397;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 2466-76-4, name is 1-(1H-Imidazol-1-yl)ethanone, 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 2466-76-4, Formula: C5H6N2O

General procedure: To a solution of N -acetylimidazole 7a (1 mmol) and a suitable Baylis-Hillman acetate 1 (1 mmol) in DMF (1 mL), K2CO3 (1 mmol) was added and the resulting mixture was stirred at room temperature until complete consumption of N -acetylimidazole 7a. The reaction mixture was then diluted with water (20 mL) and extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine and dried over anhydrous Na2SO4 . After removal of the solvent under reduced pressure, the residue was puried by flash chromatography over silica gel with EtOAc and hexane (1:1). (E)-Methyl 2-((1-imidazolyl)methyl)-3-phenylacrylate (8a) Yellow oil; yield (141 mg, 58percent); 1H NMR (500 MHz, CDCl3) : 8.03 (s, 1H), 7.48 (s, 1H), 7.42 (d, J =7.4 Hz, 3H), 7.31 (d, J = 6.8 Hz, 2H), 7.01 (s, 1H), 6.85 (s, 1H), 4.96 (s, 2H), 3.79 (s, 3H); 13C NMR (125MHz, CDCl3) : 166.9, 144.9, 137.0, 133.9, 129.7, 129.1, 129.0, 128.8, 127.0, 118.8, 52.5, 43.0; HRMS (IT-TOF); Anal. Calcd. for C14H14N2O2 : m=z 243.1128; Found [M+H]+: m=z 243.1126.

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

Reference:
Article; Koeseceli Oezenc, Ay?en; Celik, Ilhami; Koekten, ?ule; Turkish Journal of Chemistry; vol. 41; 3; (2017); p. 323 – 334;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 5955-72-6, 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. 5955-72-6 name is 2-Chloro-6-nitro-1H-benzo[d]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.

Step 3. NaH (60%) in mineral oil was added portion-wise to a stirred suspension of 2-chloro-5- nitro-lH-benzo[d] imidazole (A/1482/81/1) in dry DMF at 0 C under a nitrogen atmosphere The ice-bath was removed, and the reaction mixture was stirred at RT. After 0.5 h the mixture was cooled to 0 C, and 2-trimethylsilylethyoxymethyl chloride (0.38 mL) was added drop-wise. The ice-bath was removed, and the resulting reaction mixture was stirred at RT. After lh, UPLC showed complete conversion. A saturated ammonium chloride solution and EA were added, the organic phase was separated, washed with water, dried over sodium sulfate and the solvent removed under vacuum. The crude material was purified by FC on silica (Snap 100, eluting with Cy EA from 100/0 to 80/20) to give the desired product A/1482/82/1 as yellow oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-6-nitro-1H-benzo[d]imidazole, and friends who are interested can also refer to it.

Reference:
Patent; THE GENERAL HOSPITAL CORPORATION; ZAHLER, Robert; WESTER, Ronald Thure; BRICKNER, Steven Joseph; WO2014/176258; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 827-43-0, 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. 827-43-0 name is 4-Methyl-2-phenyl-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.

Into a 15mL pressure tube, sequentially add 1o (47.5mg, 0.3mmol), dichloromethane (3mL), 2a (84.7mg, 0.45mmol), dichloro (pentamethylcyclopentadienyl) rhodium (III) dimer (4.7mg, 0.0075 mmol) and silver acetate (100.1 mg, 0.6 mmol), then the pressure-resistant tube was sealed and placed in a 100 C. oil bath for 10 h. After the reaction was completed, the mixture was cooled to room temperature, filtered with suction, dried, and separated through a silica gel column (dichloromethane / methanol / acetic acid = 30/1 / 0.1) to obtain 3o (67.2 mg, 65%) as a white solid product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Methyl-2-phenyl-1H-imidazole, and friends who are interested can also refer to it.

Reference:
Patent; Henan Normal University; Zhang Xinying; Zhang Linghua; Xu Yuanshuang; Fan Xuesen; (23 pag.)CN110372708; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 705-09-9, name is 2-(Difluoromethyl)-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: imidazoles-derivatives

Step 1: 4-(6-bromo-2-(2-(difIuoromethyl)-lH-benzo[d]imidazol-l-yl)-8-methoxyquinazoHn-4-yl)morpholineTo a stirred mixture of 4-(6-bromo-2-chloro-8-methoxyquinazolin-4-yl)morpholine (300 mg, 0.00084 mol) and potassium carbonate (348 mg, 0.00251 mol) in N,N-dimethylformamide ( 10 ml) was added 2-(difluoromethyl)-lH-benzo[d] imidazole (169 mg, 0.001 mol) at room temperature. The reaction mixture was heated at 80C for 16 h. The reaction mixture was added to ice-cold water ( 100 mL). The solid separated was collected by filtration, washed with 5% EtOAc in hexane and dried under vacuum to afford the title compound as white solid (230 mg, 56%). H NMR (400 MHz, DMSO-d6) : delta 8.67 (d, J = 8.40 Hz, 1 H), 7.96 (t, J = 53.2 Hz, 1H), 7.87 (d, J = 8.0 Hz, 1H), 7.73 (d, J = 2.0 Hz, 1H), 7.54 (d, J = 2.0 Hz, 1H), 7.53-7.43 (m, 2H), 4.05 (s, 3H), 3.94-3.83 (m, 8H); ESI-MS : Calculated mass: 489.06; Observed mass: 490.20 [M + H]+.

The synthetic route of 705-09-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASANA BIOSCIENCES, LLC; THOMPSON, Scott, K.; SMITH, Roger, A.; REDDY, Sanjeeva; JOHN, Tyler, M.; NYAVANANDI, Vijay, Kumar; SUBRAMANYA, Hosahalli; POTLURI, Vijay; PANIGRAHI, Sunil, Kumar; NADIPALLI, Prabhakara, Rao; SENGUPTA, Saumitra; WO2014/169167; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 50995-95-4,Some common heterocyclic compound, 50995-95-4, name is 2-Propylimidazole, molecular formula is C6H10N2, 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.

Method B: A mixture of 9-(2,3,5-tri-(9-acetyl-beta-D-ribofuranosyl)-2,6-dichloropurine (1.12 g, 2.5 mmol) and 2-propylimidazole (2.20 g, 20 mmol) was dissolved in CH3CN (30 mL) and stirred at 65 C under N2 for 2 h (reaction complete, TLC). After removal of volatiles, the residue was dissolved in CH2Cl2 (200 mL) and washed (H2O, 3 x 50 mL). The aqueous phase was extracted with CH2Cl2, and the combined organic phase was dried (Na2SO4) and evaporated to dryness. The residue was chromatographed (MeOH/CH2Cl2, 1 :95) to give 9-(2,3,5-tri-O-acetyl-beta-D- ribofuranosyl)-2-chloro-6-(2-propylimidazol-l-yl)purine (977 mg, 93%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Propylimidazole, its application will become more common.

Reference:
Patent; BRIGHAM YOUNG UNIVERSITY, TRANSFER TECHNOLOGY OFFICE; WO2006/138396; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

496-46-8, name is Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. COA of Formula: C4H6N4O2

EXAMPLE 2; AFFINITYPURIFICATION OFDIMETHYLCYCLOPENTANO-CB; Dimethylcyclopentano-CB (Figure 4, Compound 3) was synthesized according to the procedures described by Day et al. (J. Org. Chem. 2001, 66, 8094) and Isobe et al. (ORG. Lett. 2002, 4, 1287), by heating at 90 C for 24 hours, a 5 : 1 mixture of glycoluril (Compound 2) and dimethylcyclopentano-glycoluril (Figure 4, Compound 3), and formaldehyde in the presence of concentrated sulfuric acid (Figure 4), so as to give the desired cucurbituril product in 30 % yield. The water-soluble fraction (740 mg) of the crude, heterogeneous mixture (1.3 gram) was dissolved in neutral water (50 ml) and passed through a column loaded with the protonated aminated resin prepared as described above, at a flow rate of 0.5 ml/minute (of the heterogeneous mixture in water). The column was then washed sequentially with water, methanol, CH2C12, and again with methanol. Removal of the solvent from the combined eluent afforded a solid residue (510 mg). This residue was used for collecting a second harvest of CB [6] using the same column, as is detailed hereinbelow. A sample of the resin was dried under reduce pressure overnight and was analyzed by FTIR. The obtained spectrum, presented in Figure 13, indicated that the resin is indeed loaded with the CB [6]. The resin-bound CB [6] was released from the column by elution with a 1: 2 mixture of TRIETHYLAMINE-DMF (100 ml) at a flow rate of 2 ml/minute. The column was thereafter washed with water (200 ml), and the combined eluent was concentrated under reduced pressure. Methanol was then added and the precipitate was collected and dried. The resultant white powder (195 mg) was analyzed BY H NMR and ESI- MS and the analyses are presented in Figures 14 and 15, respectively. As is shown in Figures 14 and 15, the resin-bound CB [6], obtained as a powder upon elution from the column, contained mainly a mixture of Compound 4 (Figure 4) and Compound 1 (Figure 2), with a small amount of di (dimethylcyclopentano) -CB [6]. Regeneration of the column was performed by washing it with 10 % (v/v) trifluoroacetic acid in CH2C12. The regenerated column was used again to harvest additional amounts of CB [6] from the CB-depleted remnants obtained in the first harvest (510 mg). That residue was dissolved in neutral water and loaded on the column as described above. Unloading the column with triethylamine-DMF yielded a second crop of pure CB [6] (165 mg). The performance of the column over multiple cycles of affinity chromatography was evaluated by loading and unloading a sample of purified CB [6] (150 mg) four times. The sample was trapped and released quantitatively in all eight operations with no apparent loss of the column capacity.

The synthetic route of 496-46-8 has been constantly updated, and we look forward to future research findings.

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

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. 32673-41-9, name is 4-Imidazolemethanol hydrochloride belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C4H7ClN2O

(A) 4-(Chloromethyl)imidazole hydrochloride (1) To a solution of 20 ml of toluene containing 2 ml of thionyl chloride was added 700 mg of 4-(hydroxymethyl)imidazole hydrochloride. The reaction mixture was heated to the refluxing temperature of the solvent for 3 hours, cooled and concentrated to dryness under reduced pressure. The title compound was obtained as a white solid (790 mg, 99% yield).

The synthetic route of 32673-41-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US5218115; (1993); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem