Category: imidazoles-derivatives

Electric Literature of 89830-98-8,Some common heterocyclic compound, 89830-98-8, name is 5-Cyclopropyl-1H-imidazole, molecular formula is C6H8N2, 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.

A suspension 2-chloro-5-fluoro-4-iodopyridine (1.8 g, 1.00 mmol), 4-cyclopropyl imidazole (982 mg, 9.10 mmol), Cu2O (100 mg, 0.700 mmol), 8-hydroxyquinoline (152 mg, 1.05 mmol), cesium carbonate (4.60 g, 14.0 mmol), and PEG-3350 (1.4 g) in butyronitrile (50 mL) was heated at 65 C. for 16 hours. The reaction mixture was filtered through Celite, concentrated and the residue was partitioned between dichlormethane and water. The layers were separated and the aqueous layer washed twice with dichloromethane. The combined organic layers were dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography (15?60% EtOAc in hexanes) to afford 2-chloro-4-(4-cyclopropyl-1H-imidazol-1-yl)-5-fluoropyridine (702 mg, 42% yield).

The synthetic route of 89830-98-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Gilead Sciences, Inc.; Notte, Gregory; US2014/179663; (2014); 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. 1450-93-7, name is 1H-imidazol-2-amine sulfate(2:1), A new synthetic method of this compound is introduced below., Formula: C6H12N6O4S

A solution of 158 mg of 2-aminoimidazole sulfate in 0.4 mL of concentrated HCl and 0.4 mL of water is cooled to 0 C. To this solution is added dropwise a solution of 82.8 mg of NaNO2 in 0.6 mL of water. The resulting yellow solution is stirred at 0 C. for 30 minutes and is added slowly to a suspension of 244 mg of 2,2,2-trifluoro-1-(4-methyl-3,4-dihydroquinoxalin-1(2H)-yl)ethan-1-one and 504 mg of NaHCO3 in 3 mL of MeOH. The reaction mixture turns red. After the addition is complete, the mixture is filtered and the orange solid collected is dried to yield the crude product, (E)-1-(7-((1H-imidazol-2-yl)diazenyl)-4-methyl-3,4-dihydroquinoxalin-1(2H)-yl)-2,2,2-trifluoroethan-1-one. This material is used in the next step without further purification

The synthetic route of 1450-93-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Procter & Gamble Company; MURPHY, Bryan Patrick; ZHANG, Guiru; ZHAO, Jielu; (32 pag.)US2018/72970; (2018); 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. 1450-93-7, name is 1H-imidazol-2-amine sulfate(2:1), This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C6H12N6O4S

[2-(2-Amino-imidazol-1-yl)-ethyl]-carbamic acid tert-butyl ester (Cpd 5b). To a flask containing 2-anninoinnidazole sulfate 5a (1 g, 3.8 mmol) in DMF (20 ml_) was added sodium hydride (0.65 g, 16.3 mmol) in small portions with stirring. The temperature was maintained below 30 0C during the addition by means of an ice bath. After stirring for 30 minutes at 25-30 0C, the solution was cooled to 0 0C and (2-bromo-ethyl)-carbamic acid tert-butyl ester (1.7 g, 7.6 mmol) in DMF (1 ml_) was added. After stirring for 1 min the cooling bath was removed and the solution was stirred toward rt for 16 h. The reaction was carefully quenched with water (10 ml_), extracted with EtOAc (4 x 10 ml_), dried over sodium sulfate, filtered, and concentrated to a residue. The residue was stored at < 0.5 mm Hg for 24 h to remove residual DMF, then purified by normal phase chromatography to give compound 5b (0.29 g) as a brown glass. HRMS calcd. for Ci0Hi9N4O2 m/z 227.1508 (M+H), found: 227.1518. According to the analysis of related databases, 1450-93-7, the application of this compound in the production field has become more and more popular. Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2009/58653; (2009); A1;,
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. 120781-02-4, name is Methyl 2-bromo-1-methyl-1H-imidazole-5-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: imidazoles-derivatives

Methyl 2-bromo-1-methyl-1 H-imidazole-5-carboxylate (659 mg) (3-cyanophenyl) boronic acid (600 mg),(1,1′-diphenylphosphinoferrocene) dichloropalladium (200 mg),2 M aqueous potassium carbonate solution (3 ml),A mixture of toluene (10 ml) and ethanol (3 ml) was stirred at 80 C. overnight.The mixture was cooled to room temperature and extracted with ethyl acetate and water. The obtained organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane / ethyl acetate) to give the title compound (239 mg)

The synthetic route of 120781-02-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; MIZOJIRI, RYO; CARY, DOUGLAS ROBERT; HIRAYAMA, TAKAHARU; ITO, MASAHIRO; TANAKA, TOSHIO; IMAEDA, YASUHIRO; SASAKI, SHIGEKAZU; TAKAMI, KAZUAKI; FUKUDA, KOICHIRO; KAMAURA, MASAHIRO; MORISHITA, NAO; (133 pag.)JP2017/222626; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 66121-69-5, 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 66121-69-5 as follows.

After dissolving 1-methylimidazole-4-carbonitrile (1.0 g, 8.0 mmol) in DMF (30 mL), trifluoroacetic hydrazide (1.9 g, 14.8 mmol)After adding and stirring at room temperature for 30 minutes.After adding sodium methoxide (28% methanol solution) to the reaction mixture, the mixture was raised to 140 C and stirred with heating for 48 hours.The reaction mixture was cooled to room temperature, the solvent was blown out, and then extracted with ethyl acetate and water. The organic layers are collected, dehydrated with sodium sulfate, the solids are filtered off and the solvent is blown off. The reaction mixture was purified using silica gel column chromatography to obtain compound (4).(0.35 g, 1.6 mmol) is obtained with a yield of 20%.

According to the analysis of related databases, 66121-69-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Samsung Electronics Co., Ltd.; Cheil Industries Inc.; Pusan National University Institute for Research & Industry Cooperation; Noh Chang-ho; Yoon Ung-chan; Kwon O-hyeon; Choi Byeong-gi; (23 pag.)KR102046153; (2019); B1;,
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. HPLC of Formula: C8H6F2N2

Step b): 4-(4-chloro-6-(2-(difluoromethvn-1 H-benzordlimidazol-l -ylVI ,3,5-triazin-2- vDmorpholine (25).Compound 24 (425 muetaetaomicronIota, 1 .0 eq.) was dissolved in DMF (2 mL) and cooled to -5C, treated with anhydrous potassium carbonate (1.44 eq.) and 2-(difluoromethyl)-1 /-/- benzo[c/]imidazole (1 .4 eq.), stirred for 30 min and further stirred at RT for 4 h. The reaction mixture was diluted with water and the precipitate was filtered and washed with small amounts of water. Purification was done by silica gel flash column chromatography.

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

Reference:
Patent; UNIVERSITY OF BASEL; CMILJANOVIC, Vladimir; CMILJANOVIC, Natasa; GIESE, Bernd; WYMANN, Matthias; WO2011/114275; (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. 13750-62-4, name is 1-Benzyl-2-methyl-1H-imidazole, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-Benzyl-2-methyl-1H-imidazole

General procedure: A solution mixture of the intermediate 3 (818 mg, 1.5 mmol) and 1,2-dimethyl imidazole (173 mg, 1.8 mmol) in acetonitrile (2 mL) was heated at 70 C for 30 h. The solvent was removed under reduced pressure, and the residue was washed with a mixture solvent (hexane/ethyl acetate = 10:1) and dried in vacuo to give an intermediate 4a, to which HCl solution (3 mL, 4 M in dioxane) was added. The reaction mixture was stirred at room temperature for 5 h and the precipitation was filtered and washed with hexane to give the Boc deprotected intermediate, which was used for the next step directly without further characterization. The Boc deprotected intermediate was subsequently neutralized by Na2CO3 (159 mg, 1.5 mmol) in MeOH (2 mL). The mixture was stirred for 5 h and the solvent was removed to dryness. The solid residue was dissolved in dry CH2Cl2 and filtered, and concentrated to give the product 5a as a white solid (550 mg, 68% yield for 2 steps).

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:
Article; Kang, Guowei; Lin, Silong; Shiwakoti, Atul; Ni, Bukuo; Catalysis Communications; vol. 57; (2014); p. 111 – 114;,
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 2963-77-1 as follows. Recommanded Product: 4-(1H-Benzo[d]imidazol-2-yl)aniline

2,3-dihydro-benzo[1,4]dioxine-6-carboxylic acid (4-formyl-phenyl)-amide (0.1 mmol, 0.0284 g), 4-(1H-benzoimidazol-2-yl)-phenylamine (0.1 mmol, 0.021 g) and NaBH(OAc)3 (1.0 mmol, 0.211 g) were stirred in DMF (2 ml) at room temperature for 24 h. Then NaBH(OAc)3 (0.5 mmol, 0.11 g) was added to the reaction. The resulting mixture was stirred at room temperature for 36 h. Water (10 ml) was added to quench the reaction. Aq. K2CO3 solution (5 %) was added to neutralize the pH to ca. 7. The formed solid was filtered and washed with water (2 x 4 ml). The title compound was obtained as brown solid (0.042 g, 88 %). 1H NMR delta 4.33-4.30 (m, 6H), 6.72-6.69 (m, 3H), 6.97 (d, J= 8.1 Hz, 1H), 7.12-7.08 (m, 2H), 7.35 (d, J= 8.1 Hz, 2H), 7.55-7.40 (m, 4H), 7.71 (d, J= 8. 1 Hz, 2H), 7.87 (d, J= 8.1 Hz, 2H), 10.02 (s, 1H), 12.41 (br s, 1H). MS m/z = 477 (M+1)

According to the analysis of related databases, 2963-77-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IMCLONE SYSTEMS INCORPORATED; WO2005/42496; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 3752-24-7, 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. 3752-24-7, name is 4,5,6,7-Tetrahydro-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 1 1-[4-(4,5,6,7-tetrahydro-1H-benzimidazol-1-yl)phenyl]carboxaldehyde A mixture of 4,5,6,7-tetrahydro-1H-benzimidazole [25.6 g, 0.21 mol, prepared by following the procedure of H. Schubert and H. Fitsche, J. Prakt, Chem 4, (7), 407 (1958)], p-fluorobenzaldehyde (26 g, 0.21 mol) anhydrous K2 CO3 (29.2 g, 0.21 mol) and CuO (300 mg) in pyridine (100 ml) is heated under reflux for 18 hours. The reaction mixture is cooled, CH2 Cl2 is added and the solution is filtered. The inorganic residue is washed exhaustively with CH2 Cl2. The filtrate and the washings are combined and evaporated to dryness. The residue is dissolved in CH2 Cl2, filtered through silica gel and the filtrate is evaporated to give 15.5 g of the product, 1-[4-(4,5,6,7-tetrahydro-1H-benzimidazol-1-yl)phenyl]carboxaldehyde, mp 104-105 C.

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, 4,5,6,7-Tetrahydro-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Warner-Lambert Company; US4717730; (1988); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 13750-62-4, A common heterocyclic compound, 13750-62-4, name is 1-Benzyl-2-methyl-1H-imidazole, molecular formula is C11H12N2, 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: 1-Benzyl-2-methylimidazole (0.32 cm3, ?2 mmol) was dissolved in acetonitrile (10 cm3) and then slowly added to warm solution of PdCl2 (0.18 g, 1 mmol) (in the synthesis of thiocyanate complex the NH4SCN (0.15 g, 2 mmol) was added) in acetonitrile (30 cm3). The mixture was refluxed for about 2 h and after the time the reaction solution was filtered and yellow single crystals were obtained by slow evaporation of the solvent. Yield: 88% for chloride complex (1) and 92% for thiocyanate analog (2).(0006)(1): IR (KBr): 3155 nuArH; 2927 nuCH; 1543 nuCN, 1497 nuC=C; 1454, 1351 delta(C-CH in the plane); 1274, 1155 delta(N-CH in the plane); 1067 delta(CH3); 750, 695 delta(Im ring).(0007)1H NMR (400 MHz, CDCl3) delta 7.43-7.26 (m, Ph), 7.17 (d, J = 1.8 Hz, Im), 7.13-7.06 (m, Ph), 6.74 (d, J = 1.8 Hz, Im), 5.03 (s, CH2), 2.92 (s, CH3).(0008)UV-Vis (acetonitrile, lambda (nm): 401.5, 276.1, 228.4, 211.5.

The synthetic route of 13750-62-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ma?ecki; Maro?; Polyhedron; vol. 50; 1; (2013); p. 452 – 460;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem