Author: Jessica.F

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

Application of 1615-14-1, 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. 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A 50-mL three-necked, round-bottomed flask, equipped with thermometer, nitrogen inlet, addition funnel, magnetic stirrer and reflux condenser was flame dried and flushed with nitrogen. The flask was charged with 25 mL of anhydrous dichloromethane. Freshly distilled 1-ethanol imidazole (1 , 0.01 mol) was added into the flask. The flask was chilled with ice-water bath and chloromethyl methyl sulfide (0.011 mol) in 15 ml_ of anhydrous dichloromethane was added cautiously into the flask with continous stirring over 30 minutes. The solution was heated under reflux for 14 hours and then allowed to cool to room temperature. The dichloromethane solvent was distilled under reduced pressure to give 76% of 3-methyl thiomethyl-3- 1-ethanol imidazolium chloride 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, 2-(1H-Imidazol-1-yl)ethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MIMOS BERHAD; AHMAD, Mohd Rais; WO2010/33014; (2010); A2;,
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. 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, A new synthetic method of this compound is introduced below., HPLC of Formula: C12H20N2O3

Example 5; Preparation of ethyl-4-(1-hydroxy-1-methylethyl)-2-propyl-1-{4-[2-(trityl tetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate4-(1-Hydroxy-1-methylethyl)-2-propyl-1H-imidazole-5-carboxylic acid ethyl ester (100 g), N-(triphenylmethyl)-5-(4′-bromomethyl biphenyl-2-yl)tetrazole (250 g), potassium carbonate (170 g) & tetra butyl ammonium bromide (15 g) in acetone (2.5 L) were refluxed for 10-16 hours. Progress of reaction was monitor by HPLC. After completion of reaction, reaction mass was cooled and filtered to remove the salts. Inorganic salts were washed with acetone (300 mL). Acetone from combine the filtrate and washings was distilled. The residue obtained was crystallized in acetonitrile to get ethyl-4-(1-hydroxy-1-methylethyl)-2-propyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate (280 g).HPLC Purity=98.5%

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; Ramanjaneyulu, Gorantla Seeta; Mohan, Bandari; Ray, Purna Chandra; Sethi, Madhuresh Kumar; Rawat, Vijendra Singh; Krishna, Yerramalla Raja; Lakshminarayana, Vemula; Srinivas, Mamidi; US2009/281327; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 39070-14-9, These common heterocyclic compound, 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, 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 alcohol18(0.50 g, 3.2 mmol) in THF (10 mL) at 0 C was added diisopropylethylamine (0.67 mL, 3.8 mmol) and methanesulfonyl chloride (0.3 mL, 0.38 mmol) and the mixture was stirred for 30 min. EtOAc (20 mL) was added and the solution washed with 1M aqueous HCl (20 mL), dried over MgSO4and solvent removed in vacuo. The crude material was purified by column chromatography (2:1, X4, EtOAc) to yield19(0.51 g, 91%) as a yellow solid, mp 99-100 C (lit. [43] mp 94-96 C). deltaH(CDCl3) 7.19 (1H, s, 4-H), 4.63 (2H, s, CH2), 4.08 (3H, s, CH3). deltaC(CDCl3) 146.4 (C-NO2), 132.9 (C), 128.6 (CH), 34.3 (CH3), 33.9 (CH2). LRMSm/z176.1 (100%, M35+ H), 178.1 (36%, M37+ H). These data are in good agreement with literature values [43].

The synthetic route of 39070-14-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Dickson, Benjamin D.; Wong, Way Wua; Wilson, William R.; Hay, Michael P.; Molecules; vol. 24; 8; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 57090-88-7, name is 1H-Imidazole-4-carbonitrile, molecular formula is C4H3N3, 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: 1H-Imidazole-4-carbonitrile

(b) 4-acetyl-1H-imidazole 1.42 g (15.3 mmol) 4-cyano-1H-imidazole are combined with 11.2 ml (33.6 mmol) 3n ethereal methyl-magnesium-bromide solution with 25 ml THF in 75 ml THF at 10° C. with cooling in the ice bath and after removal of the ice bath the mixture is stirred for another 2.5 h at ambient temperature. After the addition of another 3.5 ml (10.5 mmol) 3n ethereal methyl-magnesium bromide solution and stirring for 15 min at ambient temperature, 45 ml of 1m sulphuric acid are added and the mixture is stirred for 30 min. After the addition of 20 ml of 10n sodium hydroxide solution the organic phase is separated off, the aqueous phase is saturated with sodium chloride and extracted with ethyl acetate. The combined organic phases are dried on magnesium sulphate and evaporated down i. vac. Yield: 48percent C5H6N2O (110.11) Mass spectrum: (M+H)+=111

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 57090-88-7, its application will become more common.

Reference:
Patent; Dahmann, Georg; Gerlach, Kai; Pfau, Roland; Priepke, Henning; Wienen, Wolfgang; Schuler-Metz, Annette; Nar, Herbert; US2008/51578; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 2849-93-6,Some common heterocyclic compound, 2849-93-6, name is 1H-Benzimidazole-2-carboxylic acid, molecular formula is C8H6N2O2, 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 bispyridine ester amine compound (168 mg, 0.83 mmol) in Example 1 and benzoimidazole-2-carboxylic acid (190 mg, 1.17 mmol) were dissolved in DMF (5 m?#8467;), HBTU (402 mg, 1.25 mmol) and triethylamine (0.58 m?#8467;, 4.17 mmol) were added to the solution, and the mixture was stirred at room temperature for 24 hours. After the reaction was completed, the product was washed and filtered to yield a target compound as a white solid (247 mg, 86 %) by chromatography (methanol: dichloromethane = 1:30).

The synthetic route of 2849-93-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; EP2108649; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 5805-57-2, These common heterocyclic compound, 5805-57-2, name is (1H-Benzo[d]imidazol-2-yl)methanamine, 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.

General procedure: Compound 7 (0.5mmol) and DIPEA (0.7mmol) were mixed in anhydrous DMF (4mL) at 0C. After 45min, HBTU (0.6mmol) followed by the amine partner (8a-s; 0.55mmol) were added and stirring was continued at room temperature for 10-13h. After completion, the reaction mixture was diluted with EtOAc and washed with cold water and followed by brain solution. Then, the organic layer was dried over Na2SO4 and concentrated under the vacuum to obtain the crude product. Then, the residue was purified on flash chromatography using EtOAc/hexane or MeOH/DCM as eluent to obtain the title compounds 9a-s.

The synthetic route of 5805-57-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Omar, Hany A.; Zaher, Dana M.; Srinivasulu, Vunnam; Hersi, Fatema; Tarazi, Hamadeh; Al-Tel, Taleb H.; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 804 – 814;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem