Category: imidazoles-derivatives

Synthetic Route of 2034-22-2, 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 2034-22-2 as follows.

Preparation 15-Bromo-2-ethoxy-3H-imidazole-4-carbaldehyde 2,4,5-Tribromo-1H-imidazole (1a) (98.7 g, 324 mmol, 1.0 eq) was dissolved into 1.20 L of DCM and cooled to 0 C. To this was added DIPEA (62 mL, 360 mmol, 1.1 eq) followed by the slow addition of [beta-(trimethylsilyl)ethoxy]methyl chloride (60.2 mL, 340 mmol, 1.05 eq). The solution was slowly warmed to room temperature. After 2 hours the mixture was washed with 1M H3PO4/saturated aqueous NaCl (1:10; 2×600 mL). The organic layer was dried over MgSO4, and evaporated to dryness, yielding intermediate (1b) as faint yellow liquid that solidified on standing (137 g).Intermediate (1b) (130 g, 290 mmol, 1.0 eq) was dissolved into anhydrous EtOH (650 mL). To this was slowly added potassium t-butoxide (98.6 g, 879 mmol, 3.0 eq) and the mixture was heated to reflux for 16 hours. The mixture was then cooled to room temperature, filtered and concentrated. The resulting oil was dissolved in EtOAc (800 mL) and washed with saturated NaHCO3 (400 mL). The layers were separated and the organic was washed with saturated aqueous NaCl, dried over MgSO4, filtered and concentrated, yielding intermediate (1c) as a brown oil (115.3 g). MS m/z: [M+H+] calcd for C11H20Br2N2O2Si, 401.9 found 401.2.Intermediate (1c) (69.5 g, 174 mmol, 1.0 eq) was dissolved in anhydrous THF (600 mL) and cooled to -78 C. under nitrogen. A 2.5M solution of n-butyllithium in hexanes (72.9 mL, 180 mmol, 1.05 eq) was added dropwise and the mixture was stirred at -78 C. for 10 minutes. DMF (40 mL, 520 mmol, 3.0 eq) was then added and the mixture was stirred at -78 C. for 15 minutes and was then warmed to room temperature. The reaction was quenched with water (10 mL), diluted with EtOAc (600 mL) and was washed with water (100 mL), saturated aqueous NaCl, dried over MgSO4 and concentrated under reduced pressure. The recovered material was purified by silica gel chromatography (15-30% EtOAc:hexanes) to produce intermediate (1d) as a pale yellow oil (45 g).Intermediate (1d) (105.8 g, 303 mmol, 1.0 eq) was cooled at 0 C. in ice. TFA (300 mL) was added and the mixture was stirred at 0 C. for 15 minutes, then warmed to room temperature. After 90 minutes the mixture was concentrated under reduced pressure and redissolved in EtOAc (700 mL). The organic was washed with saturated bicarbonate (2×600 mL), saturated aqueous NaCl, dried over MgSO4, and concentrated under reduced pressure to produce a yellow solid. The material was suspended in hexanes (300 mL) and stirred at 0 C. for 30 minutes. The material was filtered and the solid was washed with cold hexanes (150 mL) to yield the title compound as a pale white solid (61.2 g). 1H-NMR (CDCl3) delta (ppm): 1.4 (m, 3H), 4.5 (m, 2H), 5.2 (s, 1H), 9.2 (d, 1H).

According to the analysis of related databases, 2034-22-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chao, Robert S.; Zhang, Weijiang; US2010/81697; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 3287-79-4,Some common heterocyclic compound, 3287-79-4, name is 5,6-Dimethyl-1H-benzo[d]imidazole-2(3H)-thione, molecular formula is C9H10N2S, 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.

2-Ethylthio-5,6-dimethylbenzimidazole (I). 0,65 g (6 mmol) Ethylbromide was added to a solution 0,89 g (0,005 mol) 2-mercapto-5,6-dimethylbenzimidazole and 0,24 g (0,006 mol) sodium hydroxide in 1 ml of water and 10 ml of ethanol. The reaction mixture was refluxed for 1.5 hr before disappearing starting thione (control by using TLS), cooled and added water. The precipitated product was filtered off, washed with water and dried under atmospheric conditions. The yield was 0,91 g (88%) of compound I, m.p. 123-124 C. (from water-ethanol).1H NMR (CDCl3), delta: 1.37 (3H, t, CH2CH3); 2,32 (6H, s, 2CH3); 3,27 (2H, q, CH2CH3); 7,31 (2H, s, ArH).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5,6-Dimethyl-1H-benzo[d]imidazole-2(3H)-thione, its application will become more common.

Reference:
Patent; Nauchno-Issledovatelsky Institut Farmakologii Rossiiskoi Akademii Meditsinskikh Nauk; US6376666; (2002); B1;,
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. 10364-94-0, name is (1H-Imidazol-1-yl)(phenyl)methanone, A new synthetic method of this compound is introduced below., Formula: C10H8N2O

General procedure: To a solution of substrate (100 mg) in 2.5 mL MeCN (dry) was added DBU (0.2 equiv.), and themixture was allowed to stir at 50 C for 10 min. 1-Benzoylimidazole (1.1 equiv.) in MeCN (dry, 0.5 mL)was added to the reaction mixture in two portions and it was allowed to stir at 50 C for 8 h. MeCNwas removed under reduced pressure and the resulting mixture was purified by flash columnchromatography (ethyl acetate/petroleum ether = 1:6 to 2:1) to afford benzoylated products.

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:
Article; Lu, Yuchao; Hou, Chenxi; Ren, Jingli; Xin, Xiaoting; Xu, Hengfu; Pei, Yuxin; Dong, Hai; Pei, Zhichao; Molecules; vol. 21; 5; (2016);,
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20034-00-8, name is (5-Nitro-1H-benzo[d]imidazol-2-yl)methanol, 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. COA of Formula: C8H7N3O3

General procedure: One of compounds 4a-4f (5 mmol) was dissolved in THF (25 mL) and DCC (1.24 g, 6 mmol), and DMAP (0.12 g, 1 mmol) was slowly added and the mixture was stirred for 30 min. Compounds 2a-2c (5 mmol) was added and the mixture was stirred for 7-9 h. The by-product, N,N’-dicyclohexylurea, was removed by filtration. The filtrate was concentrated in vacuum to give a solid which was dissolved in CH2Cl2 and the product 5a-5n was filtered off.

The synthetic route of 20034-00-8 has been constantly updated, and we look forward to future research findings.

Reference:
Letter; Zhang; Xu; Wang; Kang; Russian Journal of General Chemistry; vol. 87; 12; (2017); p. 3006 – 3016;,
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Electric Literature of 1003-21-0, A common heterocyclic compound, 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, molecular formula is C4H5BrN2, 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.

Ethyl magnesium bromide (3.0 M in diethyl ether, 21.5 mL, 64.4 mmol) was added via syringe over a few minutes to a clear colorless solution of 5-bromo-1-methyl-1H-imidazole (10.4 g, 64.4 mmol) in THF (100 mL) under a nitrogen atmosphere in an ice bath. A white precipitate formed during the addition. The mixture was removed from the ice bath and was stirred for 20 minutes, then was again cooled in an ice bath before addition of 4-chloro-N-methoxy-N-methylbenzamide (10.7 g, 53.6 mmol, Intermediate 1: step a). The resulting white suspension was stirred overnight at room temperature. The reaction was quenched by addition of saturated aqueous NH4Cl and diluted with water. The mixture was partially concentrated to remove THF and was diluted with DCM. The mixture was acidified to pH 1 with 1 N aqueous HCl, then neutralized with saturated aqueous NaHCO3. The phases were separated and the aqueous phase was further extracted with DCM. The organic extracts were washed with water, then were dried (Na2SO4), filtered, and concentrated, affording a white solid. The crude product was triturated with a mixture of EtOAc:heptanes (1:1, 150 mL). The precipitated solid was collected by vacuum filtration, washing with heptanes, to afford the title compound.

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; Janssen Pharmaceutica NV; Leonard, Kristi A.; Barbay, Kent; Edwards, James P.; Kreutter, Kevin D.; Kummer, David A.; Maharoof, Umar; Nishimura, Rachel; Urbanski, Maud; Venkatesan, Hariharan; Wang, Aihua; Wolin, Ronald L.; Woods, Craig R.; Pierce, Joan; Goldberg, Steven; Fourie, Anne; Xue, Xiaohua; US2014/107094; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 934-32-7, 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 934-32-7 as follows.

General procedure: In a 50-mL round-bottomed flask, a mixture of 2-aminobenzimidazole 1 (2 mmol), aldehyde 2a-p (2 mmol), 1,3-cyclohexadione 3 (2 mmol), and deep eutectic solvent (5 mL) was stirred at 80 C for specified time (Scheme 2, Table 2). After reaction completion (monitored by TLC), the reaction mixture was cooled to room temperature then poured into crushed ice to obtain solid product, which was filtered, dried, and recrystallized from ethanol to afford pure product.

According to the analysis of related databases, 934-32-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Mahire, Vilas N.; Patel, Vijay E.; Mahulikar, Pramod P.; Research on Chemical Intermediates; vol. 43; 3; (2017); p. 1847 – 1861;,
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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. 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C4H6N2S

3-hydroxysalicylaldehyde 5 (1 mmol), malononitrile 6 (2.1 mmol), 2-mercapto-1-methylimidazole 7 (1.1 mmol), Compound 4 (22 mol%) and ethanol (5 mL) were sequentially added to a 50 mL round bottom flask, and fully reacted to completion at 80 C (TLC followed Trace monitoring). After cooling to room temperature, suction filtration, the product was washed with a small amount of water, dissolved in N,N-dimethylformamide, filtered, and filtered. Distilled water was added, and a solid was precipitated, suction filtered, and recrystallized (DMSO) to give compound 8b in a yield of 83%.8b C17H13N6O2S 2,4–9–5-(1–1H–2-)-5H-[2, 3-b]-3- 2,4-diamino-9-hydroxy-5-(1-methyl-1H-imidazol-2-ylthio)- 5H-chromeno[2,3-b]pyridine-3-carbonitrile

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 60-56-0.

Reference:
Patent; Jiangsu Normal University; Wu Hui; Yuan Rui; Ren Xuanxuan; Fang Yue; Chen Wen; Zhou Shengliang; Zhang Peng; Wan Yu; (15 pag.)CN108610348; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 10597-52-1, A common heterocyclic compound, 10597-52-1, name is 7-Nitro-1H-benzo[d]imidazole, molecular formula is C7H5N3O2, 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.

To a suspension of sodium hydride (0.014 g, 0.607 mmol) in dry DMF (5 mL) under Ar in an ice bath was added solid Intermediate 15 (0.090 g, 0.552 mmol) in one portion, and then the ice bath was removed. After 30 minutes at room temperature, the reaction was returned to an ice bath, then ethyl iodide (0.049 ml, 0.607 mmol) added dropwise, and the reaction stirred cold. The bath was removed, and the reaction stirred at room temperature for 12 hours, then heated to 65 C. The reaction was concentrated, taken up in EtOAc and washed five times with brine, filtered through cotton, dried (Na2SO4), filtered, and concentrated. The resulting brown oil was purified by flash column chromatography (Silica gel, 0-60% EtOAc/Heptane). The product fractions were concentrated to yield the title compound.

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; WANG, Aihua; Zhang, Yan; Leonard, Kristi Anne; Hawkins, Michael; Tounge, Brett Andrew; Maharoof, Umar S.M.; Barbay, Joseph Kent; US2012/129811; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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

A mixture of 3-methoxy-4-(4-methyl-1 H-imidazol-1-yl)benzaldehyde (1.22 g, 5.64 mmol), F3 (4.30 g), piperidine (1.4 mL), and ethanol (23 ml_) was heated to 85 C for 3 h. The resulting solution was absorbed onto silica gel (18 g) and chromatographed (MeOH/aq. NH4OH/CH2CI2) to afford slightly impure compound F4 (3.59 g) as a brown foam. MS (M+1 )+ m/z calcd for C40H42FN4O3SSi+ = 705.3, found m/z = 705.4.

The synthetic route of 870837-18-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; WO2009/20580; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 147403-65-4,Some common heterocyclic compound, 147403-65-4, name is Methyl 2-ethoxy-1-((2′-(N-hydroxycarbamimidoyl)-[1,1′-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate, molecular formula is C25H24N4O4, 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 122-Ethoxy- 1 -((2′-(5-oxo-4,5-dihydro- 1 ,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)- 1H- benzo[( ]imidazole-7-carboxylic acid – azilsartan of formula IIA solution of ethyl chloroformate (2.7 g, 24.9 mmol) in dry DMF was added dropwise to a mixture of methyl 2-ethoxy-l -((2′-((hydroxyamino)iminomethyl)biphenyl-4-yl)methyl)-l H- benzo[i ]imidazole-7-carboxylate (of formula Va; 10.6 g, 23.8 mmol), dry DMF (75 ml) and pyridine (2.25 g)under stirring in an ice-cold bath under nitrogen and the mixture was stirred under cooling under nitrogen for 6 hours. The reaction mixture was poured into a separation funnel containing water (150 ml) and the mixture was extracted with ethyl acetate (5 x 100 ml). The extract was dried with MgS04 and, after evaporation, 12.7 g of a solid yellowish substance were obtained. The evaporation residue was dissolved in DMSO (200 ml) and t- BuOK (8 g, 71.3 mmol) was added under stirring and cooling and the mixture was stirred at the room temperature for 5 h. Then, the reaction mixture was poured into water (750 ml) and the resulting solution was acidified with 5 % HCl. The separated product was aspirated, washed with water and air-dried. 1 1.2 g (the quantitative yield would be ca. 10.9 g) of a product containing 88.3 % of azilsartan of formula II according to HPLC was obtained. Crystallization from isopropanol provided 9.3 g (85.5%) of azilsartan of formula II with the HPLC content of 98.7% with the melting point of 205 to 208 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-ethoxy-1-((2′-(N-hydroxycarbamimidoyl)-[1,1′-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate, its application will become more common.

Reference:
Patent; ZENTIVA, K.S.; RADL, Stanislav; STACH, Jan; WO2012/139535; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem