Category: imidazoles-derivatives

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. 143722-29-6, name is 1-(4-Bromobenzyl)-2-butyl-4-chloro-1H-imidazole-5-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 1-(4-Bromobenzyl)-2-butyl-4-chloro-1H-imidazole-5-carbaldehyde

Example 3. Preparation of 3-(4-bromobenzyl-2-butyl-5-chloro-3h-imidazol-4-yl)-methanol (II) A round-bottom flask is loaded with 0.6 g of 3-(4-bromobenzyl)-2-butyl-5-chloro-3H-imidazole-4-carboxaldehyde and 5 ml of methanol. The mixture is cooled to 0-5C and added with 78 mg of sodium borohydride. Stirring is continued for 30′, then 5 ml of a saturated ammonium chloride solution are added. The solvent is evaporated off and the residue is taken up with 10 ml of ethyl acetate. After two washings with 5 ml of water the organic phase is evaporated to give 480 mg of a crude residue, which is crystallized from ethanol-water. 320 mg of 3-(4-bromobenzyl-2-butyl-5-chloro-3H-imidazol-4-yl)-methanol are obtained as colourless crystals.

The synthetic route of 143722-29-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dipharma S.p.A.; EP1548009; (2005); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 32673-41-9, name is 4-Imidazolemethanol hydrochloride, 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. Quality Control of 4-Imidazolemethanol hydrochloride

Step A Preparation of 1-triphenylmethyl-4-(hydroxymethyl)imidazole To a solution of 4-(hydroxymethyl)imidazole hydrochloride (35 g) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which was sufficiently pure for use in the next step.

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

Reference:
Patent; Merck & Co., Inc.; US5780492; (1998); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

14741-71-0, name is Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate, 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. Application In Synthesis of Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate

Method A 2-Benzimidazol-2-yl-N-(4-cyano(3-pyridyl))acetamide LiHMDS (2.5 eq) was added to ethyl 2-benzimidazol-2-ylacetate (1.0 eq) in THF at -78 C. After 1 hour, 3-amino-4-cyanopyridine (0.8 eq) in THF was added. The resulting mixture was allowed to warm to room temperature overnight. The mixture was quenched with NH4Cl (aqueous saturated solution) and extracted with EtOAc. The organic layer washed with H2O and brine, dried over Na2SO4, filtered, and concentrated in vacuo to yield a brown solid. The crude material was purified by silica gel chromatography (5:1 EtOAc:hexane) to yield the desired product. LC/MS m/z 278.3 (MH+), Rt 1.88 minutes.

The synthetic route of 14741-71-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Renhowe, Paul A.; Machajewski, Timothy; Shafer, Cynthia M.; Wernette-Hammond, Mary Ellen; Pecchi, Sabina; US2002/103230; (2002); 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. 16681-56-4, name is 2-Bromo-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Formula: C3H3BrN2

To a solution of 2-bromo-1H-imidazole (300.00 mg, 2.04 mmol, 1.00 eq) in THF (5.00 mL) was added batchwise NaH (106.00 mg, 2.65 mmol, 60% purity, 1.30 eq) at 0C. After addition, the mixture was stirred at this temperature 0.5 h, and then 2-(chloromethoxy) ethyltrimethylsilane (442.14 mg, 2.65 mmol, 470.36 uL, 1.30 eq) was added dropwise at 0C. The resulting mixture was stirred at 20C for 15.5 h. It was quenched by addition water 50 mL, and extracted with EtOAc (20 mLx3), dried over Na2SO4, filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (SiO2, PE/EtOAc =20/1 to 5:1) to afford the title compound (500.00 mg, 1.80 mmol, 88.41% yield) as a colorless oil.

The synthetic route of 16681-56-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MARINEAU, Jason, J.; ZAHLER, Robert; CIBLAT, Stephane; WINTER, Dana, K.; KABRO, Anzhelika; ROY, Stephanie; SCHMIDT, Darby; CHUAQUI, Claudio; MALOJCIC, Goran; PIRAS, Henri; WHITMORE, Kenneth, Matthew; LUND, Kate-Iyn; SINKO, Bill; SPROTT, Kevin; (418 pag.)WO2018/13867; (2018); 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. 71759-88-1, name is 5-Iodo-1-methyl-1H-imidazole, A new synthetic method of this compound is introduced below., Product Details of 71759-88-1

[1845] 5-Iodo-1 N-methylimidazole (455 mg, 2.18 mmol) was dissolved in 10 mL THF at room temperature. EtMgBr (2.4 mL, 1.0 M in THF) was added dropwise. After 30 mins, the reaction mixture was cooled to 0 C. 10 mL THF solution of CuCN (175 mg, 1.96 mmol) and LiCl (166 mg, 3.9 mmol) was then added. 10 mins later, Compound (782) from Step A above (989 mg, 1.96 mmol, in 10 mL THF) was added. The reaction was stirred overnight. Sat. NH4Cl solution was added to quench the reaction. The resulting emulsion was filtered through a sintered funnel and the filtrate was extracted with EtOAc twice. The organic layer was washed with NaHCO3 solution and brine, dried over magnesium sulfate, filtered and evaporated in vivo. The resulting crude material was chromatographed on a silica gel column (using 1:1 hexanes/EtOAc then 10:1 CH2Cl2/MeOH) to obtain 330 mg of the title product. MS M+1=506 The enantiomers were seperated on a chiral AD column.

The synthetic route of 71759-88-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhu, Hugh Y.; Njoroge, F. George; Cooper, Alan B.; Guzi, Timothy; Rane, Dinanath F.; Minor, Keith P.; Doll, Ronald J.; Girijavallabhan, Viyyoor M.; Santhanam, Bama; Pinto, Patrick A.; Vibulbhan, Bancha; Keertikar, Kartik M.; Alvarez, Carmen S.; Baldwin, John J.; Li, Ge; Huang, Chia-Yu; James, Ray A.; Bishop, W. Robert; Wang, James J-S; Desai, Jagdish A.; US2003/229099; (2003); 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. 822-36-6, name is 4-Methyl-1H-imidazole, A new synthetic method of this compound is introduced below., Formula: C4H6N2

A suspension of 3- bromo-5-(trifiuoromethyl)aniline (4.8 g, 20 mmol), 4-methylimidazole (1.97 g, 24 mmol), potassium carbonate (3.04 g, 22 mmol), CuI (0.57 g, 3 mmol), and 8-hydroxyquinoline (0.44 g, 3 mmol,) in dry DMSO (20 mL) in a pressure tube was degassed by bubbling N2 into the suspension for 10 minutes while stirring. The tube was sealed tightly. The mixture was heated at 120 0C (oil bath temperature) for 15 h. The mixture was cooled down to 45- 50 0C and 14% aq. NH4OH (20 mL) was added. The mixture was maintained at this temperature for 1 h. After cooling to rt, water and ethyl acetate were added. The aqueous layer was extracted with ethyl acetate and the combined organic layers were passed through a short silica gel column to remove most of green/blue Cu salts. The filtrate was dried over sodium sulfate and concentrated on a rotavap. The crude product was recrystallized from EtOAc/hexanes, giving pure pale yellow needles. The mother liquor was concentrated and the residue was purified on silica gel column (5% methanol/methylene chloride), yielding a second crop as pale yellow needles.

The synthetic route of 822-36-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARIAD PHARMACEUTICALS, INC.; WO2007/75869; (2007); A2;,
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. 4331-29-7, name is 1H-Benzo[d]imidazol-7-amine, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H7N3

4-Chloro-6,7-dimethoxy-quinazoline (100 mg, 0.4500 mmol) and 1H-indazol-6-amine (59.27 mg, 0.4500 mmol) were mixed in MeCN (2 mL) and irradiated in a CEM microwave at 100 °C for one hour. The reaction mixture was allowed to cool and then passed through a short pad of silica. After concentration of the filtrate, the resultant solid was washed sequentially with acetonitrile and diethyl ether and dried in vacuo to give 16 (0.13g, 81percent) as a light brown solid. 1H NMR (DMSO-d6) delta 13.21 (br s, 1H), 11.37 (s, 1H), 8.84 (s, 1H), 8.30 (s, 1H), 8.12 (s, 1H), 7.94 (s, 1H), 7.85 (d, J=8.6 Hz, 1H), 7.41 (d, J=8.6 Hz, 1H), 7.34 (s, 1H), 4.03 (s, 3H), 4.01 (s, 3H)

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 4331-29-7.

Reference:
Article; Jordan, Allan M.; Begum, Habiba; Fairweather, Emma; Fritzl, Samantha; Goldberg, Kristin; Hopkins, Gemma V.; Hamilton, Niall M.; Lyons, Amanda J.; March, H. Nikki; Newton, Rebecca; Small, Helen F.; Vishwanath, Swamy; Waddell, Ian D.; Waszkowycz, Bohdan; Watson, Amanda J.; Ogilvie, Donald J.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 11; (2016); p. 2724 – 2729;,
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. 13435-22-8, name is 1-Butyl-2-methyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 1-Butyl-2-methyl-1H-imidazole

General procedure: 1,2-Dimethyl imidazole (9.61 g; 0.10 mol) and trimethylphosphate (14.01 g; 0.10 mol) were mixed at room temperature under argon and vigorous stirring, then heated to 80C and stirred at this temperature for 1h. Acetonitrile (20 mL) was added and the mixture was stirred at 80C for 23h. The mixture was left at room temperature, the precipitate was separated,washed twice with acetonitrile and dried under vacuum (2 Torr) for 4 h at 80C.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 13435-22-8.

Reference:
Article; Zicmanis, Andris; Anteina, Liene; Tetrahedron Letters; vol. 55; 12; (2014); p. 2027 – 2028;,
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. 3034-50-2, name is Imidazole-4-carbaldehyde, A new synthetic method of this compound is introduced below., Computed Properties of C4H4N2O

Synthesis of 1-Trityl-1H-imidazole-4-carbaldehyde STR49 To dimethylformamide (100 mL) was added imidazole-4-carboxaldehyde (10 g, 0.104 mol, Aldrich Chemical Corp.) and triethylamine (20.5 mL, 0.147 mol). A solution of trityl chloride (40 g, 0.143 mol) in dimethylformamide (300 mL) was added, followed by stirring at 25 C. for 6 hours. The solvent was removed in vacuo, and the residue was dissolved in ethyl acetate (1.5 L) and 1N citric acid (350 mL). The phases were separated, and the organic phase was washed with brine, dried over anhydrous magnesium sulfate, and filtered. Concentration of the solution in vacuo gave a white solid, 27.59 g, 78% yield. NMR was consistent with structure. MS: APCI: M-1: 337.2 (M: 338.41).

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; Warner-Lambert Company; US6143766; (2000); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 288-32-4, These common heterocyclic compound, 288-32-4, name is 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.

To a solution of imidazole 9A (20 g, 294 mmol) in THF (200 mL) and TEA (40 g, 400 mmol) was added dimethylsulfamoyl chloride (55 g, 383 mmol) slowly at 0 C. The mixture was stirred at room temperature overnight. The reaction mixture was poured into 300 mL of water and extracted with ethyl acetate (3x). The solution was washed with water and brine, dried over Na2S04, then concentrated to dryness to give compound 9B (42 g, 89%) as a colorless oil, which solidified after standing at room temperature for 1 h. The solid material was used directly in the next step without further purification. 1H NMR (400 MHz, CDC13) delta 7.86 (s, 1H), 7.23 (s, 1H), 7.11 (s, 1H), 2.82 (s, 6H).

The synthetic route of 288-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NEUROPORE THERAPIES, INC.; STOCKING, Emily, M.; WRASIDLO, Wolfgang; WO2015/116663; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem