Month: August 2021

Application of 10597-52-1, 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. 10597-52-1 name is 7-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 B: Preparation of tert-butyl 4-nitro-1H-benzo[d]imidazole-1-carboxylate: Triethylamine (1.03 mL, 7.36 mmol) was added to a suspension of 4-nitro-1H-benzo[d]imidazole (1.0 g, 6.13 mmol) in dichloromethane (50 mL), followed by addition of Boc2O (1.61 g, 7.36 mmol). The reaction was stirred at room temperature for 16 hours and then quenched with water (20 mL). The aqueous layer was extracted with dichloromethane (50 mL*3), and the combined organics were dried, filtered and concentrated. The crude product was purified by flash column chromatography, eluding with hexanes/ethyl acetate (4:1) to give the desired product (1.50 g, 93%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 7-Nitro-1H-benzo[d]imidazole, and friends who are interested can also refer to it.

Reference:
Patent; Array Biopharma, Inc.; US2010/63066; (2010); 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. 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Formula: C5H6N2O

3-Methyl-3H-imidazole-4- carbaldehyde (10) (4.0 g, 15 mmol) was suspended in THF (10 mL), and the resulting solution cooled to 0C. Lithium aluminum hydride (300 mg, 32.0 mmol) was added portion wise over 10 minutes, and the resulting suspension stirred for a further 10 minutes. Excess hydride was quenched by the addition of solid Na2SO4-IOH2O (~1 g) in large portions with vigorous stirring. Additional THF was added as needed to prevent solidification of the resulting slurry. The resulting suspension was stirred for a further hour, and then filtered to remove the sulfate salts, and the solvent was removed under reduced pressure to provide the title alcohol (1.3 g, 80%). 1H NMR (400 MHz, ^-MeOH): delta 7.57 (s, IH), 6.89 (s, IH), 4.58 (s, 2H), 372 (s, 3H). 13C NMR (100 MHz, ^-MeOH): delta 140.1, 132.7, 128.1, 31.9, 31.0.

The synthetic route of 39021-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YALE UNIVERSITY; UNIVERSITY OF SOUTH FLORIDA; UNIVERSITY OF WASHINGTON; SEBTI, Said; WO2006/102159; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 492-98-8, name is 1H,1’H-2,2′-Biimidazole, 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 492-98-8, Formula: C6H6N4

General procedure: 2,2′-Biimidazole (0.4 g, 3 mmol) was added to a 100mLthree-necked flask charged with 3-chloropropionic acid (1.3 g,12 mmol), KOH (0.336 g, 6 mmol), and water (10 mL) at roomtemperature. The reaction mixture was adjusted to a pH level of10 to 12 with a 5M aqueous solution of KOH and the reactionmixture was heated slowly to reflux for 8 h. The product mixturewas acidified to pH2-3 with hydrochloric acid (1 M), and thenconcentrated under reduced pressure. The concentrated mixturewas diluted with ethanol and filtered to remove the undissolvedsalt. The final filtrate was concentrated to give a brown viscousliquid (85.1% yield). The product was dried overnight undervacuum before use and analysis.

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

Reference:
Article; Feng, Miaona; Zhao, Guoying; Gao, Hongling; Zhang, Suojiang; Australian Journal of Chemistry; vol. 68; 10; (2015); p. 1513 – 1517;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 14741-71-0, name is Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate, 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 14741-71-0, Quality Control of Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate

General procedure: To the dry solid of compound 3 (2.04 g, 0.01 mol) ammonium acetate (0.50 g) eithercyclophentanone (0.78 g, 0.01 mol) or cyclohexanone (0.92 g, 0.01 mol) were added. Thereaction mixture was heated in an oil bath at 120 oC for 1 h then left to cool. The product wastriturated with ethanol and the formed solid product was collected by filtration

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate, and friends who are interested can also refer to it.

Reference:
Article; Mohareb, Rafat M.; Gamaan, Marwa S.; Bulletin of the Chemical Society of Ethiopia; vol. 32; 3; (2018); p. 541 – 557;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 19225-92-4, name is 2-(Chloromethyl)-1-methyl-1H-imidazole, 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 19225-92-4, Recommanded Product: 2-(Chloromethyl)-1-methyl-1H-imidazole

[1-[3-(1-Methyl-1H-imidazol-2-ylmethoxymethyl)-phenyl]-1 H-imidazole-4- carboxylic acid ethyl ester] (14a)To a suspension of NaH (308 mg, 7.7 mmol, 60% in mineral oil) in dry THF (6 ml_) under N2 atmosphere was added a solution of alcohol 7 (410 mg, 1.38 mmol) in THF (2 ml_) while stirring for 30 min at room temperature. The reaction mixture was cooled to O0C and the compound 14 (crude 200 mg, 1.53 mmol) in THF (1 ml_) was added dropwise and allowed to come to room temperature during a period of 30 min after which it was refluxed for 12 h. The mixture was quenched with ice water (5 ml_), acidified to pH 2-3 by adding aqueous HCI solution (2N). The reaction mixture was extracted with CH2CI2 (3 x 20 ml_), washed with brine, dried over Na2SO4 and concentrated. The crude mass was taken in ethanol (10 ml_), purged HCI gas for 30 min. and stirred at room temperature for 3 h. After evaporation of solvent, the crude mass was purified by column chromatography using 28% ethylacetate in hexane to furnish 14a (150 mg, 25%) as a white solid, mp-83.8-88.6C.

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

Reference:
Patent; NEUROSEARCH A/S; WO2007/42545; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 41716-18-1, 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. 41716-18-1 name is 1-Methyl-1H-imidazole-4-carboxylic acid, 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.

Production Example 8 N-[(2-Bromopyridin-4-yl)methyl]-N-cyclobutyl-1-methyl-1H-imidazole-4-carboxamide After a solution of methyl-1H-imidazole-4-carboxylic acid (300 mg), 2-(1H-7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate methanaminium (HATU) (1.27 g) and diisopropylethylamine (431 mg) in dimethylformamide (7 mL) was stirred at room temperature for 15 min, N-[(2-bromopyridin-4-yl)methyl]cyclobutanamine (574 mg) was added thereto and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with chloroform, and washed with saturated aqueous sodium hydrogen carbonate solution. After extraction with chloroform, the organic phase was dried over anhydrous magnesium sulfate. After the desiccant was filtered off, the solvent was distilled off under reduced pressure. The resulting residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=80:20-50:50) to afford the title compound (1.46 g). 1H NMR (600 MHz, CHLOROFORM-d) d ppm 1.55-2.26 (m, 6H), 3.60-3.81 (m, 3H), 4.56-6.50 (m, 3H), 7.04-8.29 (m, 5H) (ESI pos.) m/z: 349([M+H]+), 351([M+3]+)

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

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD.; Moriya, Minoru; Yasuhara, Akito; Sakagami, Kazunari; Ohta, Hiroshi; Abe, Kumi; Yamamoto, Shuji; Araki, Yuko; Urabe, Hiroki; Sun, Xiang-Min; US2013/184460; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route 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.

Example 22 Synthesis of 1-tritylimidazole (5) To a solution of trityl chloride (5.58 g, 20.0 mmol.) in dry methylene chloride (100 ml) cooled down to 0° C. and stirred under Ar, was added dropwise over 1.5 hours a solution of imidazole (1.36 g, 20.0 mmol.) and triethylamine (2.7 mml, 20 mmol.) in 50 ml dry methylene chloride. At the end of the addition, the reaction mixture was allowed to warm up to room temperature and stirred under Ar at that temperature overnight. The reaction mixture was then washed with 20 ml of a 10percent solution of ammonium chloride, then with 20 ml of distilled water. The organic phase was dried over magnesium sulfate and evaporated in vacuo to yield quantitatively a white solid. Recrystallization from methylene chloride/hexanes yielded 5.60 g of (5) (yield=90percent after recrystallization). m.p. 214° C.; 1H NMR (200 MHz, CDCl3) delta7.43 (m, 1H, NCHN), 7.3-7.4 (m, 9H, 3*C6H5), 7.1-7.2 (m, GH, 3*C6H5), 7.0 (m, 1H, Ph3CNCH=CH), 6.81 (m, 1H, Ph3CNCH=CH); 13C NMR (50 MHz, CDCl3) delta142.3, 139.0, 129.6, 128.2, 128.3, 121.6.

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

Reference:
Patent; McGill University; US6476216; (2002); B1;,
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. 96797-15-8, name is 4-Iodo-1-trityl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Safety of 4-Iodo-1-trityl-1H-imidazole

A mixture of 4-iodo-1-(triphenylmethyl)-1H-imidazole (Intermediate A, 4.36 g, 9.99 mmol), (2-formylphenyl)boronic acid (1.65 g, 11.00 mmol), Pd(PPh3)4 (1.16 g, 1.0 mmol) and K3PO4 (4.25 g, 20.02 mmol) in DMF (40 mL) and water (8 mL) was stirred at 100 C. for 16 h under N2 atmosphere. The reaction mixture was diluted with water (100 mL) and extracted with ethyl acetate (150 mL*2). The organic phases were combined, washed with brine and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was purified by flash chromatography eluting with EtOAc in hexane (1% to 25% gradient) to yield 2-(1-trityl-1H-imidazol-4-yl)benzaldehyde as yellow solid (3 g, 72%). MS: m/z=415.1 [M+H]+.

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 96797-15-8.

Reference:
Patent; Merck Patent GmbH; SHERER, Brian A.; (167 pag.)US2016/75711; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, 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 33543-78-1, Formula: C6H8N2O2

a solution of 13.3 g of ethyl imidazole-2-carboxylate in 145 ml of anhydrous dimethylformamide is added dropwise over 20 minutes at a temperature of between 20° C. and 25° C. to a suspension of 3.4 g of 80percent sodium hydride in 45 ml of anhydrous dimethylformamide maintained under a nitrogen atmosphere. After stirring for 15 minutes, a solution of 26 g of 2-bromo-5-fluoro-1-indanone in 190 ml of anhydrous dimethylformamide is added dropwise over 10 minutes at the same temperature. The mixture is stirred for 1 hour 30 minutes and then, after slow addition of 100 ml of water, poured over 3800 ml of distilled water and extracted 4 times with a total of 3800 ml of chloroform. The organic extracts are pooled, washed with 950 ml of distilled water, dried over anhydrous sodium sulphate and concentrated to dryness under reduced pressure (15 mmHg; 2 kPa) at 40° C. The product obtained (27 g) is chromatographed on 1490 g of neutral silica gel (0.020-0.045 mm) contained in a column 9.6 cm in diameter, eluding under pressure with a dichloromethane-ethyl acetate mixture (70-30 by volume) and collecting 80 ml fractions. Fractions 13 to 70 are pooled and concentrated to dryness under reduced pressure (15 mmHg; 2 kPa) at 40° C. 13.4 g of ethyl 1-(5-fluoro-1-oxo-2-indanyl)imidazole-2-carboxylate are thus obtained which melt at 127° C. The 2-bromo-5-fluoro-1-indanone can be prepared in the following manner:

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, Ethyl 1H-imidazole-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Rhone-Poulenc Rorer S.A.; US5677306; (1997); 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. 71759-87-0, name is 4-Iodo-1-methyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C4H5IN2

To a microwave tube was added 4-iodo-l -methyl- 1H-imidazole (2.00 g, 9.62 mmmol) and CuCN (1.03 g, 11.5 mmol) in DMA (12 mL). The reaction mixture was heated at 180 C in a microwave reactor for 45 min. The reaction mixture was concentrated in vacuo. The residue was suspended in EtOAc/sat. NH4Cl/NH4OH (add NH4OH to sat NH4Cl to pH=9) and stirred for 30 min. The organic phase was separated, washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to afford 580 mg of the title compound as a light brown solid.

The synthetic route of 71759-87-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2009/70485; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem