Month: July 2021

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. 38993-84-9, name is (1-Methyl-1H-imidazol-5-yl)methanol, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 38993-84-9

Add thionyl chloride (4.00 ml, 53.8 mmol) to a solution of (3-methyl-3H- imidazol-4-yl)-methanol (4.0 g, 35.7 mmol) in dichloroethane (30 mL) and stir at room temperature for 18 h. Concentrate the reaction mixture and add ether to the residue. Sonicate for 5 min, filter, and dry to give the title compound (5.8 g, 98percent). MS (ES+) 131 (M+l)+. 1H NMR (400 MHz, DMSO-d6): delta 14.99 (s, 1H), 9.18 (s, 1H), 7.75 (s, 1H), 5.00 (s, 2H), 3.85 (s, 3H).

According to the analysis of related databases, 38993-84-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELI LILLY AND COMPANY; WO2006/66174; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 17289-26-8, name is 1-Methyl-1H-imidazole-4-carbaldehyde, molecular formula is C5H6N2O, 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. COA of Formula: C5H6N2O

A mixture of i-methyMH-imidazole-4-carbaldehyde (0.50 g), N- bromosuccinimide (0.89 g) and chloroform (7.0 ml_) was heated at reflux for 2 hours. The mixture was cooled to O0C, diluted with saturated aqueous sodium carbonate solution (10 ml_) and extracted with dichloromethane. The combined organic extract was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with a mixture of ethyl acetate and dichloromethane (0:1 to 7:10 by volume) to afford the title compound as a white solid (0.37 g).1H NMR (CDCl3): delta 3.70 (s, 3H), 7.66 (s, 1 H), 9.89 (s, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 17289-26-8, its application will become more common.

Reference:
Patent; ARGENTA DISCOVERY LIMITED; WO2009/77728; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 172499-76-2, name is Ethyl 3-(1H-imidazol-2-yl)propanoate, molecular formula is C8H12N2O2, 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. Application In Synthesis of Ethyl 3-(1H-imidazol-2-yl)propanoate

(ii) Production of ethyl 3-[1-[4-[4-[[2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazol-4-yl]methoxy]phenyl]butyl]-1H-imidazol-2-yl]propionate A suspension of 4-[[4-(4-iodobutyl)phenoxy]methyl]-2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazole (6.00 g), ethyl 3-(1H-imidazol-2-yl)propionate (3.83 g) and potassium carbonate (1.58 g) in DMF (100 ml) was stirred at 70C for 23 hr. The reaction mixture was combined with water and extracted with ethyl acetate. The extract was successively washed with water and saturated brine and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; ethyl acetate) and washed with diethyl ether-hexane to give the titled compound (3.69 g) as a colorless amorphous form.1H-NMR (CDCl3) delta: 1.25 (3H, t, J = 7.2 Hz), 1.59-1.79 (4H, m), 2.59 (2H, t, J = 7.0 Hz), 2.88-2.91 (4H, m), 3.87 (2H, t, J = 7.0 Hz), 4.14 (2H, q, J = 7.2 Hz), 5.02 (2H, d, J = 0.8 Hz), 6.79 (1H, d, J = 1.4 Hz), 6.90-7.06 (6H, m), 7.10 (1H, s), 7.52-7.69 (5H, m). IR (KBr): 1732, 1510, 1325, 1167, 1123, 1067 cm-1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 172499-76-2, its application will become more common.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1439178; (2004); 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, Safety of Ethyl 1H-imidazole-2-carboxylate

Ethyl 1H-imidazole-2-carboxylate at 0 C(40.01 g, 285.5 mmol) in a dry THF (600 mL) suspension Sodium hydride (13.82 g, 345.5 mmol, mass fraction 60%) was added.The reaction mixture was stirred at room temperature for 1 hour and then cooled to 0 C.O-(2,4-dinitrophenyl)hydroxylamine (80.00 g, 401.8 mmol) was added portionwise.The reaction system was stirred at room temperature overnight and then diluted in water (600 mL).The resulting mixture was extracted with EA (600 mL×10).The separated organic phase was dried over anhydrous sodium sulfate, filtered and evaporated.The residue obtained is purified by silica gel column chromatography (EA/PE (v/v) = 1/2 to 1/1 to 2/1).The title compound is a brown solid(37.6 g, yield 85%).

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:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Li Xiaobo; Li Minxiong; Zhang Tao; Hu Haiyang; Wu Yanjun; (102 pag.)CN108570048; (2018); A;,
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. 15965-54-5, name is 2-Chloro-5-methoxy-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-Chloro-5-methoxy-1H-benzo[d]imidazole

Preparation 21 tert-Butyl 2-chloro-5-methoxy-1H-1,3-benzimidazole-1-carboxylate STR66 Di-tert-butyldicarbonate (523 mg) was added to a solution of 2-chloro-5-methoxy-1H-1,3-benzimidazole (364 mg) and dimethylaminopyridine (24 mg) in acetonitrile (4 ml). The reaction mixture was stirred at room temperature for 30 minutes, after which time the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica gel eluding with a solvent gradient of 90:10 changing to 85:15, by volume, hexane:ethyl acetate to afford tert-butyl 2-chloro-5-methoxy-1H-1,3-benzimidazole-1-carboxylate (470 mg) as an off-white solid, as a 1:1 mixture of regioisomers. 1 H-NMR (CDCl3)delta: 7.80 (0.5H, d), 7.55 (0.5H, d), 7.50 (0.5H, s), 7.15 (0.5H, s), 7.00 (1H, t), 3.85 (3H, s), 1.70 (9H, s).

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 15965-54-5.

Reference:
Patent; Pfizer Inc; US6166011; (2000); A;,
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 7189-69-7 as follows. Recommanded Product: 7189-69-7

To a solution of phenethylamine (34, 0.15mmol) in THF (5mL), triethylamine (0.15mmol) was added. To this mixture, 1,1′-sulfonyldiimidazole (0.15mmol) was added and the reaction mixture was stirred at 60C for 2h. After the completion of the reaction monitored by TLC, water was added and the reaction mixture was extracted using ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. The obtained intermediate 36 was used for next step without further purification. In the next step, 3-phenylpropylamine (0.15mmol) was dissolved in THF and triethylamine (0.15mmol) was added. To this mixture, 36 was added. The reaction was stirred at 60C for 3h. The reaction was monitored by TLC. After the completion of the reaction, the reaction mixture was quenched with water and the whole mixture was extracted using ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude mixture was purified by column chromatography to afford the pure product 3. Yield 72%, Pale yellow solid. Rf 0.30 (2: 1 Ethylacetate: Hexane), mp. 135-137C; IR (neat): 3362, 2950, 2822, 1560, 1523, 1345, 1170, 945cm-1. 1H NMR (CDCl3) delta 1.79-1.87 (m, 2H), 2.64 (t, J=8.00Hz, 2H), 2.85 (t, J=7.20Hz, 2H), 2.92-2.97 (m, 2H), 3.28-3.33 (m, 2H), 4.07-4.13 (m, 2H), 7.15-7.33 (m, 10H); 13C NMR (CDCl3) delta 31.13, 32.94, 35.81, 42.68, 44.31, 126.35, 127.04, 128.50, 128.71, 128.97, 128.98, 138.10, 141.04. HRMS Calcd for C17H22N2O2S m/z [M+H] 319.1481, found 319.1507.

According to the analysis of related databases, 7189-69-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Manickam, Manoj; Jalani, Hitesh B.; Pillaiyar, Thanigaimalai; Sharma, Niti; Boggu, Pulla Reddy; Venkateswararao, Eeda; Lee, You-Jung; Jeon, Eun-Seok; Jung, Sang-Hun; European Journal of Medicinal Chemistry; vol. 134; (2017); p. 379 – 391;,
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. 150058-27-8, name is Methyl 2-ethoxy-1H-benzo[d]imidazole-7-carboxylate, A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 2-ethoxy-1H-benzo[d]imidazole-7-carboxylate

To a solution of methyl 2-ethoxy-lH-benzo[d]imidazole-7-carboxylate (55.5 mg, 0.252 mmol) in DMF (2 mL) was added sodium hydride (60percent) (16.78 mg, 0.420 mmol) at RT. The reaction mixture was stirred for 10 min at RT before methyl 4″-(bromomethyl)- [l,l’:3′, l”-terphenyl]-4′-carboxylate (Intermediate 400b, 80 mg, 0.210 mmol) was added in its own solution of DMF (1 niL). After 50 min of stirring at RT the reaction mixture was diluted with EtOAc and washed with 10percent LiCl (aq). The organic phase was dried over MgS04, filtered over celite, and concentrated. The residue was dissolved DMF and purified by ISCO (0-100percent EtOAc/Hexanes) to afford the title compound (Intermediate 314a, 48 mg, 0.069 mmol, 33.0 percent yield). LC-MS Retention time (Method A2) = 1.20 min. Found m/z: 520.1 (M+H)+. H NMR (400MHz, CDC13) delta 7.89 (d, 7=8.1 Hz, 1H), 7.66 – 7.57 (m, 4H), 7.55 – 7.49 (m, 2H), 7.49 – 7.31 (m, 4H), 7.22 (d, 7=8.4 Hz, 2H), 7.01 (d, 7=8.1 Hz, 2H), 5.66 (s, 2H), 4.68 (q, 7=7.1 Hz, 2H), 3.78 (s, 3H), 3.57 (s, 3H), 1.54 – 1.48 (m, 3H).

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; UNIVERSITE DE MONTREAL; BRISTOL-MYERS SQUIBB COMPANY; PRIESTLEY, Eldon, Scott; REZNIK, Samuel, Kaye; RUEDIGER, Edward, H.; GILLARD, James, R.; HALPERN, Oz, Scott; JIANG, Wen; RICHTER, Jeremy; RUEL, Rejean; TRIPATHY, Sasmita; YANG, Wu; ZHANG, Xiaojun; (642 pag.)WO2018/5591; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 152628-02-9,Some common heterocyclic compound, 152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, molecular formula is C19H20N4, 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 4. 4′-[[4-Methyl-6-(1-methyl-2-benzimidazolyl)-2-propyl-1-benzimidazolyl]methyl]-2-biphenylcarboxylic acid (telmisartan) (4′-Methyl-2′-propyl-1H-benzimidazol-6′-yl)-1-methyl benzimidazole (3.0 g, 9.8 mmol), 4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzyl methanesulfonate (3.12 g, 10 mmol), tetrahydrofuran (15 ml) and potassium carbonate (1.38 g, 10 mmol) are loaded into a round-bottom flask equipped with magnetic stirrer, condenser and under nitrogen atmosphere. The mixture is stirred at room temperature for 8 hours, then 10% hydrochloric acid is added to pH=2. THF is evaporated off, which causes precipitation of boronic acid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, its application will become more common.

Reference:
Patent; Dipharma S.p.A.; EP1719766; (2006); 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. 616-47-7, name is 1-Methyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C4H6N2

General procedure: N-methyl imidazole (17.53 ml, 0.22 mol) and 1,4-butane sultone (20.5 ml, 0.20mol) were dissolved in toluene (60 ml) and stirred for 8h at 60ºC under nitrogen atmosphere. The white zwitter ion solid so formed was filtered and washed repeatedly with diethyl ether (3 × 40 ml) to remove non-ionic residues.The resulting solid (MIM-BS) was dried in vacuum for 8h. The MIM-BS (10.0 gm,0.0463 mol) was dissolved in water (2 ml) with constant stirring.Methanesulfonic acid (3 ml, 0.0463 mol) was taken in water (1 ml) and added to the reaction contents dropwise. The mixture was stirred for 6h at 85ºC. After completion of the reaction, water was removed and contents were dried for 24h under reduced pressure. The resulting colorless viscous liquid was stored in dry box for further use.

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 616-47-7.

Reference:
Article; Garg, Bhaskar; Ling, Yong-Chien; Tetrahedron Letters; vol. 53; 42; (2012); p. 5674 – 5677;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 14486-52-3, The chemical industry reduces the impact on the environment during synthesis 14486-52-3, name is 1-Methyl-2-(methylthio)imidazole, I believe this compound will play a more active role in future production and life.

General procedure: 1-Methylimidazole (0.49 g, 6.05 mmol) was added to a stirred solution of Key Intermediate-1 (2.3 g, 4.03 mmol) in acetonitrile (25 mL) at RT. The reaction mixture was heated to 90 C for 16 h and concentrated under reduced pressure. The crude material was triturated with diethyl ether (2 x 10 mL) to afford a brown solid (2.4g) which was used in the next steps without further purification. M/z 616.38 (M)+ TFA: H2O (9:1, 20 mL) was added to the brown solid (2.4 g) at RT. The reaction mixture was stirred for 3 h and concentrated under reduced pressure. The resulting crude product was triturated with diethyl ether (2 x 5 mL) and dried under high vacuum. The crude product was purified by preparative HPLC affording the title product as off-white solid (515 mg, 30% over 2 steps).

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, 1-Methyl-2-(methylthio)imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Antabio SAS; DAVIES, David; LEIRIS, Simon; (56 pag.)EP3572411; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem