Category: imidazoles-derivatives

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

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

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

Electric Literature of 615-16-7, 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. 615-16-7 name is 2-Hydroxybenzimidazole, 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.

General procedure: 4-Bromo-2-(substituted) benzonitrile 5a or 5b (5 mmol) was added to a mixture of 1H-benzo[d]imidazol-2(3H)-one (6) (10 mmol) and Cs2CO3 (10 mmol) in DMF (25.0 ml). After 12 h, 50 ml of ice water was added dropwise. The resulting suspension was filtered, and the filter cake was dried in a vacuum oven. The solid was purified by flash chromatography (50 % ethyl acetate in hexane) to afford 4-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)-2-(substituted) benzonitrile (7a or 7b). 2-(Trifluoromethyl)-4-(1,2-dihydro-2-oxobenzo[d]imidazol-3-yl) benzonitrile (7a) Yield 62 %; White Solid; mp 232-233 C; IR (KBr) nu max: 3189, 3149 (N-Hstretch), 3072 (C-Harom), 2957, 2895, 2820 (C-Halk), 2230 (C:N), 1720 (C=O), 1611 (N-Hbend), 1575, 1507, 1481, 1439 (C=Carom), 1385, 1319, 1240, 1185, 1127, 1053 (C-Hbend), 1272, 558 (C-CF3) cm-1; 1H NMR (400 MHz, CDCl3, ppm): delta 9.372 (s, 1H, NH), 8.14 (s, 1H, H-2), 8.03 (d, 2H, H-5,H-6), 7.2 (m, 4H, phenyl); 13C NMR (100 MHz, CDCl3, ppm): delta 152.9 (C=O), 139.2 (C4), 135.6 (C6), 133.8, 133.1 (q, J = 65 Hz, C2), 128.5 (C0 1), 127.6 (d, J = 34 Hz, C5), 123.3 (C0 6), 122.8 (C0 3), 122.5 (q, CF3), 121.6 (C), 120.4 (C0 5), 114.8 (CN), 110.0 (C0 2), 108.7 (C0 4), 106.6 (C1); HRMS (ESI): m/z calculated for C15H8F3N3O [M?H]?: 304.06922; Found: 304.069.

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

Reference:
Article; Elancheran; Saravanan; Choudhury, Bhaswati; Divakar; Kabilan; Ramanathan; Das, Babulal; Devi; Kotoky, Jibon; Medicinal Chemistry Research; vol. 25; 4; (2016); p. 539 – 552;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 32673-41-9,Some common heterocyclic compound, 32673-41-9, name is 4-Imidazolemethanol hydrochloride, molecular formula is C4H7ClN2O, 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.

Step 1 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 title compound as a white solid which was sufficiently pure for use in the next step.

The synthetic route of 32673-41-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US6015817; (2000); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 45676-04-8, 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. 45676-04-8, name is 1-tert-Butylimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

The procedure given for the synthesis of [DPCP-(ImidMe)2]Cl2 was followed. Yield: 92%. mp: 170-173 C. 1H NMR (400 MHz, CDCl3): delta 12.00 (s, 2H, imidazole-NCHN), 8.47 (s, 2H, imidazole-NCHCHN), 8.10 (s, 2H, imidazole-NCHCHN), 7.73 (m, 6H, Ph-H), 7.62 (m, 4H, Ph-H), 1.90 [s, 18H, C(CH3)3] ppm. 13C NMR (100 MHz, CDCl3): delta 159.86, 137.69, 134.90, 131.27, 129.76, 129.03, 128.22, 127.61, 122.01, 119.29, 62.83, 30.35 ppm. 31P (161 MHz, CDCl3): delta 41.89 ppm (s).

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

Reference:
Article; Senkuttuvan; Ramakrishna; Bakthavachalam; Reddy, N. Dastagiri; Journal of Organometallic Chemistry; vol. 723; (2013); p. 72 – 78;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 641571-13-3,Some common heterocyclic compound, 641571-13-3, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)benzoic acid, molecular formula is C12H9F3N2O2, 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.

(VII) (10 g), t-butanol (300 mL), triethylamine (7.9 g) and diphenylphosphoryl azide (11.2 g) were added to a 500 mL reaction flask. The mixture was heated to reflux and refluxed for 16 hours then cooled to room temperature. The solvent was removed by evaporation under reduced pressure. The residue was treated with water (150 mL) and extracted with ethyl acetate (2 x 150 mL). The extracts were combined, washed with brine (150 mL), dried over sodium sulfate and evaporated to remove the solvent under reduced pressure to give the crude product (12.5 g).The above crude product (12.5 g), n-propanol (125 mL), p-xylene (125 mL) and solid sodium hydroxide (7.3 g) were added to a 500 mL reaction flask. The mixture was stirred and the mixture was heated to reflux and refluxed for 30 hours. Stirring was stopped, water (162 mL) was added and the azeotrope was distilled off under reduced pressure. The residue was diluted with water (20 mL), cooled to 0 & lt; 0 & gt; C, stirred slowly for 1 h and filtered. The filter cake was washed with water (2 x 30 mL) and dried in vacuo at 55 C to give 7.1 g of the solid compound (I). The HPLC purity was 98.7% and the overall yield of the two-step reaction was 79.5%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)benzoic acid, its application will become more common.

Reference:
Patent; Esteve Huayi Pharmaceutical Co., Ltd; Zhao, Liqiang; Wang, Zhao; Jiang, Hong; Dong, Jin; Xu, Xiaofei; Zheng, Guorong; (9 pag.)CN105985293; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]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 152628-02-9, Formula: C19H20N4

l-Ethyl-2-[4′-(bromomethylphenyl)]benzoate (30.30 g, 85.5%) was dissolved in N1N- dimethylformamide (100 ml) at 2 + 20C and 4-methyl-6-(l -methyl- 1-benzimidazolyl)- 2-propyl-l-benzimidazole (25 g) at 2 +/- 20C was added to the above solution followed by sodium hydroxide (3.42 g). Thereafter, stirring was continued at 2 +/- 20C till the completion of the reaction. Methylene chloride (125 ml) was added to the above reaction mass followed by DM water (250 ml, 22 +/- 20C) at 2 +/- 20C. Stirring was continued at 22 +/- 20C for 15 min and the layers were separated and the aqueous layer was extracted with methylene chloride (25 ml) at 22 +/- 20C. The combined organic extract was washed with DM water (125 ml) at 22 +/- 20C and the organic layer was concentrated till the mass temperature reaches to 6O0C at atmospheric pressure. Ethanol (75 ml) was added to the concentrated mass (Contains Telmisartan ethyl ester) at 600C and the concentration was continued till the vapor temperature reaches to 820C. The concentrated mass was cooled to 45 + 5 and diluted with ethanol (100 ml) followed by aqueous sodium hydroxide (prepared by dissolving 10.87 g of sodium hydroxide in 25 ml of DM water) at 45 + 50C in 15 +/- 5 min was added and the contents were heated to reflux at 78 +/- I0C. Thereafter, stirring was continued at reflux temperature (78 +/- I0C) till completion of the reaction. The reaction mass was concentrated at atmospheric pressure till the mass temperature reaches to 80 +/- 20C and DM water (375 ml, 28 +/- 20C) was added to the residue followed by methylene chloride (50 ml) and stirred for 10 min at 22 + 20C. The layers were separated and methylene chloride (200 ml) was added to the aqueous layer at 22 + 20C and pH was adjusted to 4.1 +/- 0.1 with hydrochloric acid (-17 ml, 30%w/w) and stirring was continued for 10 min at 22 +/- 20C. The layers were separated and the organic layer was washed with DM water (50 ml) at 28 + 20C. The organic layer was diluted with LambdazetaN-dimethylformamide (125 ml) at 28 + 20C and seeded with Telmisaratn Form A. Thereafter, the solution was kept on standing at 28 +/- 20C for 30 min and Telmisartan Form A crystallizes out. The resulting slurry was concentrated at atmospheric pressure till the mass temperature reaches to 84 +/- 20C. The slurry was cooled to 2 +/- 20C and stirred for Ih at this temperature. The product was filtered and washed with pre-cooled N,iV-dimethylformamide (25 ml, 0 +/- 20C) followed by pre-cooled ethanol (50 ml, O0C) and dried to obtain Telmisartan (30 g ) was having more than 99.7 % of HPLC purity.

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, 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AUROBINDO PHARMA LIMITED; KORRAPATI, Venkata Vara Prasada Rao; INTI, Venkata Subramanyeswara Rao; ANANTA, Rani; MEENAKSHISUNDERAM, Sivakumaran; WO2010/4385; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 15469-97-3, name is 1-Trityl-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 15469-97-3, Application In Synthesis of 1-Trityl-1H-imidazole

Take the imidazole salt (395 mg, 0.5 mmol), 1-trityl imidazole (550 mg, 1.8 mmol), anhydrous potassium carbonate (61 mg, 4.4 mmol), palladium dichloride (78.5 mg, 44 mmol) After vacuuming with nitrogen, anhydrous THF (6 mL) was added and the mixture was refluxed for 20 h. After the reaction solution was cooled to room temperature, it was diluted with dichloromethane, and the crude product was purified by column chromatography.The pale yellow product was obtained 278 mg, yield 53percent.

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

Reference:
Patent; Tianjin Normal University; Liu Guiyan; Han Fangwai; Liu Chengxin; Xu Ying; (9 pag.)CN108690086; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 3034-42-2, name is 1-Methyl-5-nitroimidazole, 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 3034-42-2, Recommanded Product: 3034-42-2

General procedure: To a solution of 1-methylimidazole derivatives (1 mmol) in adequate volume of acetonitrile, was added 1.5 mmol of 2-bromoacetophenone (1.8 mmol of ethylbromoactate). The reaction mixture was refluxed. When the reaction was(TLC), the solvent volume was reduced and the crude product was then filtered off and washed with cold acetonitrile.

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-5-nitroimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Bahnous, Mebarek; Bouraiou, Abdelmalek; Chelghoum, Meryem; Bouacida, Sofiane; Roisnel, Thierry; Smati, Farida; Bentchouala, Chafia; Gros, Philippe C.; Belfaitah, Ali; Bioorganic and Medicinal Chemistry Letters; vol. 23; 5; (2013); p. 1274 – 1278;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem