Category: imidazoles-derivatives

Synthetic Route of 144690-33-5, The chemical industry reduces the impact on the environment during synthesis 144690-33-5, name is Ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2′-(1-trityl-1H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate, I believe this compound will play a more active role in future production and life.

In the equipped with electric stirrer, condenser and a thermometer of the 500 ml three-necked flask, add 20.00g (27.93mmol) intermediate I, 3.13g (55.87mmol) KOH and 80g acetone, for 55 C stirring for 3 hours (TLC monitoring), after the stop of the reaction, to cool down to 20 – 30 C, concentrated to no longer under the dripped, for 1M hydrochloric acid to adjust the pH=3, a large number of white solid precipitated, stirring at the room temperature 1 – 2h, filtering, the filter cake drying added 60 ml ethyl acetate at room temperature beating, filtering, the filter cake is dried to obtain the 11.50g impurities (see Figure 3) F, HPLC: 98.55%, yield: 59.77%.

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 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2′-(1-trityl-1H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Tsingtao Yellow Sea Pharmaceutical Co., Ltd.; Liu Chuanfei; Chen Xiaotao; Li Yanshun; Wang Jiahui; Liu Ningning; Yang Kebao; (15 pag.)CN106831727; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 144689-93-0, These common heterocyclic compound, 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, 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 15 Ethyl 1-[(2′-t-butoxycarbonylbiphenyl-4-yl)methyl]-4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate (Compound No. 1-119) Following a procedure similar to that described in Example 1(a), but using 0.845 g of ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate (prepared as described in Preparation 9) and 1.22 g of t-butyl 4′-bromomethylbiphenyl-2-carboxylate, 1.31 g of the title compound were obtained as a gum. This compound was allowed to stand at room temperature, which caused it to crystallize. It was then recrystallized from a mixture of diisopropyl ether and hexane, to give pure title compound, melting at 90-91 C. Nuclear Magnetic Resonance Spectrum (CDCl3) delta ppm: 0.97 (3H, triplet, J=7 Hz); 1.23 (3H, triplet, J=7 Hz); 1.25 (9H, singlet); 1.60 (6H, singlet); 1.82 (2H, sextet, J=7 Hz); 2.67 (2H, triplet, J=7 Hz); 4.24 (2H, quartet, J=7 Hz); 5.51 (2H, singlet); 5.72 (1H, singlet); 6.87-7.85 (8H, multiplet).

Statistics shows that Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate is playing an increasingly important role. we look forward to future research findings about 144689-93-0.

Reference:
Patent; Sankyo Company, Limited; US5616599; (1997); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 870837-18-6, 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. 870837-18-6 name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, 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.

Aqueous hydrogen peroxide (30%, 18.9 mL) was added drop-wise over 20 minutes to a solution of 3-methoxy-4-(4-methyl-1/-/-imidazol-1-yl)benzaldehyde (5.0 g, 20.0 mmol) and potassium hydroxide (6.1 g, 92.5 mmol) in MeOH (38 mL) and water (6.6 mL) at 65 C. Following completion of the addition the reaction was stirred at room temperature for an additional 25 minutes. The reaction was then allowed to cool to room temperature and was acidified with cone. HCI. The resulting precipitate was filtered to provide the title compound as a white solid. Yield: 4.6 g, 17.1 mmol, 74%. MS (APCI) m/z 232.9 (M+1 ). 1H NMR (400 MHz, CD3OD) 2.45 (br s, 3H), 4.00 (s, 3H), 7.65 (br s, 1 H), 7.67 (d, J=8.4 Hz, 1 H), 7.82 (dd, J=8.3, 1.6 Hz, 1 H), 7.89 (d, J=1.6 Hz, 1 H), 9.24 (d, J=1.6 Hz, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER INC.; ALLEN, Martin, Patrick; AM ENDE, Christopher, William; BRODNEY, Michael, Aaron; DOUNAY, Amy, Beth; JOHNSON, Douglas, Scott; PETTERSSON, Martin, Youngjin; SCHWARZ, Jacob, Bradley; TRAN, Tuan, Phong; WO2010/100606; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 36947-69-0, name is 2-(tert-Butyl)-1H-imidazole, molecular formula is C7H12N2, 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. Safety of 2-(tert-Butyl)-1H-imidazole

Step c: 2-tert-butyl-N,N-dimethyl- 1H- imidazole- 1 -sulfonamide[0465] 2-tert-Butyl-lH- imidazole (0.5 g, 4.03 mmol) was added to a suspension of 60% sodium hydride (0.5 g, 12.1 mmol) in DMF (6.0 mL) at 0C and the mixture was stirred for 0.5 h. Then N,N-dimethylsulfamoyl chloride (0.7 g, 4.84 mmol) was added dropwise and the reaction mixture was stirred at room temperature for 2 h. Saturated NH4CI solution was added and the resulting mixture was extracted with ethyl acetate. The combined extracts were washed with brine, dried over anhydrous Na2S04 and concentrated. The residue was purified by flash column chromatography on silica gel (DCM/MeOH = 20: 1 to 5: 1) to afford 0.8 g of the title compound as a white solid (86%> yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 36947-69-0, its application will become more common.

Reference:
Patent; ZENOBIA THERAPEUTICS, INC.; BOUNAUD, Pierre-Yves; NIENABER, Vicki; STEENSMA, Ruo, W.; LOWE, John, A., III; WO2012/178015; (2012); 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. 1074-59-5, name is 3-(1H-Imidazol-4-yl)propanoic acid, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C6H8N2O2

3-(1-Triphenylmethyl-4-imidazolyl)propionic acid 3-(4-Imidazolyl)propionic acid (1.0 g, 7.1 mmol) was suspended in a mixture of dichloro-methane (5 ml) and acetonitrile (25 ml). Trimethylsilyl chloride (781 mg, 7.2 mmol) was added and the mixture refluxed for 4 hours. Triethylamine (1 ml) was added, and refluxing continued for 15 minutes. Cooled, triethylamine (1 ml) added followed by chlorotriphenylmethane (1.99 g, 7.1 mmol) in dichloromethane (10 ml), and the mixture stirred at ambient temperature for 2 hours. MeOH (20 ml) was added, the mixture stirred for 30 minutes, then evaporated to dryness. Water (50 ml) was added to the residue, and the pH adjusted to 8-8.5 with triethylamine. The precipitate was filtered off, washed with diethyl ether, and dried to give the desired product (2.25 g). MS (ESP): 383 (MH+) for C25H22N2O2 NMR (DMSO-d6) delta: 2.48 (t, 2H); 2.77 (t, 2H); 6.65 (s, 1H); 7.08 (d, 6H); 7.29 (s, 1H); 7.36 (m, 9H); 12.10 (br, 1H).

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 1074-59-5.

Reference:
Patent; Syngenta Limited; US2003/144263; (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. 1219741-19-1, name is 5-Chloro-6-iodo-2-(methylsulfonyl)-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C8H6ClIN2O2S

Et3N (20.95 mL, 150 mmol) and 2-(trimethylsilyl)ethoxy methyl chloride (17.29 mL, 98 mmol) were added to a solution of Intermediate IA (26.8 g, 75 mmol) in THF (200 mL). The reaction was stirred at rt for 1 h. Volatiles were removed and the residue partitioned between EtOAc and water. The organic phase was washed with 2N aqueous HCl and brine, dried (MgSO4) and concentrated to afford the title compound as a white solid. LC-MS: calculated for C14H20ClIN2O3SSi 485.97, observed m/e 428.83 (M + H)+(Rt 2.30 min).

The synthetic route of 1219741-19-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; METABASIS THERAPEUTICS, INC.; BOOKSER, Brett, C.; DANG, Qun; GIBSON, Tony, S.; JIANG, Hongjian; CHUNG, De Michael; BAO, Jianming; JIANG, Jinlong; KASSICK, Andy; KEKEC, Ahmet; LAN, Ping; LU, Huagang; MAKARA, Gergely, M.; ROMERO, F., Anthony; SEBHAT, Iyassu; WILSON, David; WODKA, Dariusz; WO2010/47982; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 3012-80-4, name is 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde, 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 3012-80-4, Quality Control of 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde

General procedure: Benzimidazole 1 or 2 (1 mmol)was added to the mixture of TfOH (1 mL) or H2SO4 (2 mL) and arene (2-18 mmol). Reactionmixture was stirred at room temperature for the time as indicated in Table 3 or Scheme 2. Themixture was poured into ice water (30 mL). After extraction with CH2Cl2 (3 × 30 mL), thecombined extracts were consequently washed with water (50 mL), saturated aqueous solution ofNa2CO3 (30 mL), water (50 mL), dried with anhydrous Na2SO4 and evaporated in vacuo to givecrude products, which was subjected to chromatographic separation on silica gel using petroleumether/diethyl ether as an eluent.

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-1H-benzo[d]imidazole-2-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Ryabukhin, Dmitry S.; Turdakov, Alexey N.; Soldatova, Natalia S.; Kompanets, Mikhail O.; Ivanov, Alexander Yu.; Boyarskaya, Irina A.; Vasilyev, Aleksander V.; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1962 – 1973;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1632-83-3, name is 1-Methylbenzimidazole, 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. Recommanded Product: 1-Methylbenzimidazole

In an oven dried nitrogen purged 3 neck 100 mL round bottom flask, 1.00 g (7.57 mmol) of 1 -methylbenzimidazole in 20 mL of dry tetrahydrofuran is cooled to -78C. 10.69 mL (18.17 mmol) of 1.7 M t-butyllithium in hexanes is added and the reaction mixture is stirred at -780C. for 1 h. 2.55 g (11.36 mmol) of NIS in 20 mL of dry tetrahydrofuran is added. Reaction is removed from bath and stirred at room temperature for 1 hour, quenched with saturated aqueous solution of ammonium chloride, and diluted with dichloromethane. The layers are separated, the aqueous is extracted 3X100 mL dichloromethane, dried (MgSO4), and concentrated. The crude mixture is purified by EPO chromatography using hexanes:ethyl acetate as a solvent system. The product containing fractions are combined to obtain 0.400 g of the title compound, 21% yield. MS, ES+ = 259.0 (M+l); 1H NMR (DMSO-d6) 57.580-7.552 (m, 2H); 7.228-7.129 (m, 2H); 3.750 (s, 3H) ppm.

The synthetic route of 1632-83-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2006/107784; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 50995-95-4,Some common heterocyclic compound, 50995-95-4, name is 2-Propylimidazole, molecular formula is C6H10N2, 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.

General procedure: A vessel with a magnetic stirrer bar was charged with imidazole derivative (0.5 mmol), CuI (10 mg, 0.05 mmol), Cs2CO3 (0.33 g, 1 mmol), PPh3 (26 mg, 0.1 mmol) and tetrabutylammonium bromide (TBAB) (0.2 g, 0.6 mmol) under a nitrogen atmosphere. The reaction vessel was evacuated and backfilled with nitrogen three times. In a separate flask, a solution of dry dioxane (2 mL) containing the 1,1-dihalo-1-alkenes (1 mmol) was evacuated and back-filled with nitrogen gas three times. The dioxane solution was then added to the reaction flask via a syringe and the reaction mixture heated to 100 C for 30 hours. The reaction mixture was cooled to room temperature, quenched with 5 mL of a saturated NH4Cl solution, and extracted with ethyl acetate (3 x 10 mL). The combined organic phases were dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by flash column chromatography with ethyl acetate (EA) and petroleum ether (Pet) as the eluent to afford the corresponding products:

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

Reference:
Article; Wang, Man-Gang; Yu, Hua; Wu, Jun; Shang, Zhi-Cai; Journal of Chemical Research; vol. 37; 9; (2013); p. 570 – 573;,
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. 52099-72-6, name is 1-(Prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one, A new synthetic method of this compound is introduced below., category: imidazoles-derivatives

Step A: Ethyl 2,3-dihydro-3-(1-methyl-ethenyl)-2-oxo-1H-benzimidazol-1-butanoate A solution of 19 g of 1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one [described in J. Chem. Soc. Perkins, 1982, p. 261] in 150 ml of dimethylformamide was added with stirring at 20 C.+-2 C. to 5.75 g of sodium hydride as a 50% suspension in oil and 10 ml of dimethylformamide and the mixture was stirred for another 30 minutes. 23.4 g of ethyl 4-bromo-butyrate were added to the mixture over 15 minutes and the mixture was stirred at room temperature for 4 hours and was poured into 800 ml of iced water. The mixture was extracted with ether and the organic phase was washed with water, dried and evaporated to dryness under reduced pressure to obtain 33 g of ethyl 2,3-dihydro-3-(1-methyl-ethenyl)-2-oxo-1H-benzimidazol-1-butanoate.

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; Roussel Uclaf; US4585770; (1986); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem