Month: June 2021

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

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

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

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

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

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

Reference of 1457-58-5, The chemical industry reduces the impact on the environment during synthesis 1457-58-5, name is 2-Methyl-1H-imidazole-5-carboxylic acid, I believe this compound will play a more active role in future production and life.

a) (S)-N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-2-methyl-1H-imidazole-4-carboxamide 2-Methyl-1H-imidazole-4-carboxylic acid (29.0 g, 230 mmol), 335 ml of DMF and 165 ml of DCM were placed in to the reaction vessel under nitrogen. HBTU (7.27 g, 19.18 mmol), EDCI (44.1 g, 230 mmol) and 66.8 ml of DIPEA were added. (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile (50 g, 192 mmol) was added and the reaction stirred overnight at RT. 600 ml of water was slowly added and water phase was washed with 335 ml and 500 ml of DCM. DCM phases were combined, washed with 3*600 ml of water and distilled to dryness. Acetonitrile (300 ml) was added and the mixture was heated up to 75 C. Water (300 ml) was added at >60 C., solution was allowed to cool to RT for precipitation and the mixture was stirred overnight at RT. Stirring was continued for additional 2 h at <10 C. The precipitate was filtered, washed with cold ACN:water and dried under vacuum to obtain 47 g of crude product. The title compound was recrystallized from EtOH with 75% yield. 1H-NMR (400 MHz, DMSO-d6): delta 1.08 (d, 3H), 2.30 (s, 3H), 4.23-4.48 (m, 3H), 6.95 (d, 1H), 7.41 (s, 1H), 7.82 (d, 1H), 7.95-8.07 (m, 3H), 8.09-8.12 (m, 1H), 12.12 (bs, 1H). 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-Methyl-1H-imidazole-5-carboxylic acid, other downstream synthetic routes, hurry up and to see. Reference:
Patent; ORION CORPORATION; Toermakaengas, Olli; Wohlfahrt, Gerd; Salo, Harri; Ramasurbamanian, Rathna Durga; Patra, Pranab Kumar; Martin, Arputharaj Ebenezer; Heikkinen, Terhi; Vesalainen, Anniina; Moilanen, Anu; Karjalainen, Arja; US2014/94474; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, 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 60-56-0, SDS of cas: 60-56-0

General procedure: To a slurry of the substituted imidazole-2-thione or pyrimidine-2-thiol (1.0 mmol) and sodium methoxide (2.2 mmol) in methanol (20 mL) was added a solution of substituted 2-(chloromethyl)-pyridine (1.0 mmol) in methanol (10 mL). After the mixture was refluxed with stirring for 4-6 h, the solvent was removed in vacuo and the residue was washed with water to remove the salt, and then extracted with dichloromethane (3 9 10 mL) at room temperature. The solid product was directly obtained by the removal of solvent and further dried at 45 C overnight. The purity of the product was tested by HPLC and characterization of the product was confirmed by IR, 1H NMR, and mass spectroscopies. Data 3-Methyl-[4-(2,2,2-Trifluoroethoxy)-2-Pyridinyl]-Methylthio-1-Methyl-Imidazole (3a) White solid. Yield: 84.5 %. IR (cm-1): 832.7 (-CH2-S-). 1H NMR (CDCl3) delta (ppm): 2.18 (s, 3H, -CH3 in py), 3.23 (s, 3H, -CH3 in imidazole), 4.42 (q, J = 6.0 Hz, 2H,-OCH2CF3), 4.56 (s, 2H, -CH2S-), 6.62 (d, J = 5.6 Hz,1H, H in py), 6.81 (s, 1H, H in imidazole), 6.92 (s, 1H,H in imidazole), 8.30 (d, J = 5.6 Hz, 1H, H in py). MS (EI): m/z calcd. C13H14N3OF3S (M+) 317.3311, found 317.3336.

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:
Article; Ma, Sen; Jia, Ai-Quan; Fan, Fang-Fang; Shi, Hua-Tian; Zhang, Qian-Feng; Journal of Chemical Crystallography; vol. 46; 3; (2016); p. 137 – 143;,
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. 1964-77-8, name is 5-Bromo-2-methyl-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C8H7BrN2

The reactor was charged with palladium(II) acetate (0.160 g, 0.71 1 mmol), 2,8,9-triisobutyl- 2,5,8,9-tetraaza-l-phosphabicyclo[3.3.3]undecane (0.507 mL, 1.421 mmol), and 5-bromo-2- methyl- lH-benzo[d]imidazole (1.5 g, 7.1 1 mmol). The vessel was evacuated and refilled with N2 for 3 cycles and degassed dioxane (14.21 mL) was added, followed by NaHMDS (28.4 mL, 28.4 mmol). The reaction was stirred at 25C for 20 min before 2-(3-fluorophenyl)acetonitrile (73.3 mg, 0.543 mmol) was added. The reaction was then capped and heated at 100C for 3 h. More NaHMDS (6 mL) was added and the reaction was stirred for another 1 h; More NaHMDS (4 mL) was added and the reaction was stirred for another 1 h before it was cooled to room temperature, and quenched with water. The aqueous layer was extracted with EtOAc (3x), washed with brine, dried over MgS04, filtered, and the filtrate was concentrated in vacuo. The crude material was purified by chromatography on silica gel (eluent: 0-100% A in B. A: 10% MeOH in DCM; B: DCM.). LCMS calc. = 266.10, found = 266.04 (M+H)+.

The synthetic route of 1964-77-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MOCHIDA PHARMACEUTICAL CO., LTD.; ZHANG, Ting; CHEN, Yi-Heng; GUO, Liangqin; HRUZA, Alan; JIAN, Tianying; LI, Bing; MENG, Dongfang; PARKER, Dann, L., Jr.; SHERER, Edward, C.; WOOD, Harold, B.; SAKURADA, Isao; (130 pag.)WO2016/94260; (2016); 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. 930-62-1, name is 2,4-Dimethylimidazole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2,4-Dimethylimidazole

A solution of methyl mesylate (25.4 mL, 300 mmol) in acetone (50 mL) was added dropwise to a stirred mixture of 2,4-dimethylimidazole (25.00 g, 260 mmol), potassium carbonate (55.20 g, 400 mmol) and acetone (500 mL). Stirring under argon was then continued at room temperature for 16 hours. The resulting solid was filtered off, and the solvent was removed under reduced pressure. The residue was triturated with THF (200 mL) to give crystalline product (59-3) (14.47 g, 25% yield).The filtrate was treated with activated charcoal, filtered through a layer of Celite, and the solvent was removed under reduced pressure. Upon storage of the residue at room temperature, some crystalswere formed, and these crystals were separated, washed with THF and dried in a vacuum oven to give1,2,4-trimethylimidazole (59-1) (4.01 g, 14% yield). Concentration of the filtrate gave a mixture of isomeric imidazoles (59-1) and (59-2) (12.19 g, 43% yield).

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 930-62-1.

Reference:
Patent; NITTO DENKO CORPORATION; STANISLAW, Rachwal; HU, Yufen; ZHANG, Hongxi; (0 pag.)WO2018/161025; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem