Category: imidazoles-derivatives

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. 2034-22-2, name is 2,4,5-Tribromoimidazole, A new synthetic method of this compound is introduced below., Formula: C3HBr3N2

dimethyl sulfoxide (300 mL) suspension of (2S)-2-{[4-(methoxy)phenoxy]methyl}oxirane (10.9 g), 2,4,5-tribromo-1H-imidazole (14.3 g) and cesium carbonate (18.4 g) was stirred for 4 hours at 130C . The reaction mixture was allowed to cool to room temperature, after the addition of water and ethyl acetate, the organic layer was separated and the water layer. The aqueous layer was extracted twice with ethyl acetate, combined organic layer, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (Reveleris, mobile phase: hexane / ethyl acetate = 90/10 ~ 50/50; v / v) to give the title compound (Intermediate 1: 4.73 g, pale yellow oil) was obtained .

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; TAISHO PHARMACEUTICAL CO LTD; URABE, HIROKI; NISHIKAWA, RIE; TAMIDA, TOMOKO; HATTORI, NOBUTAKA; SAKAGAMI, KAZUNARI; MATSUDA, YOHEI; YASUHARA, AKITO; (67 pag.)JP2015/6994; (2015); 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. 492-98-8, name is 1H,1’H-2,2′-Biimidazole, This compound has unique chemical properties. The synthetic route is as follows., name: 1H,1’H-2,2′-Biimidazole

General procedure: A mixture of Zn(NO3)2·6H2O (0.1mmol, 30mg), H2biim (0.1mmol, 13mg), H2pzdc (0.1mmol, 20mg) and H2O (8mL) was adjusted to pH 5.0 with 0.05 mol L-1 NaOH solution. It was then sealed in a 25mL Teflon reactor and heated at 150 C for 72 h. Finally the mixture was cooled to room temperature at a cooling rate of 3C h-1 and block colorless crystals of 1 were obtained by filtration. 1 was washed with distilled water and dried in air. Yield: 47% based on the Zn(II) salt.

According to the analysis of related databases, 492-98-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yang, Fei-Fei; Wang, Xiao-Fang; Yu, Xiao-Yang; Luo, Yu-Hui; Zhang, Hong; Polyhedron; vol. 98; (2015); p. 40 – 46;,
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. 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C6H8N2O2

Description 43; N-(3-Fluorophenyl)-1-(1H-imidazol-2-ylcarbonyl)-4-piperidinamine (D43); Ethyl imidazole-2-carboxylate (701 mg, 5.0 mmol) and D12 (971 mg, 5.0 mmol) were dissolved in toluene (25 ml) and flushed with argon. This solution was cooled to 0° C. and treated with trimethylaluminium (7.5 ml, 2M solution in hexanes, 15 mmol). The mixture was then warmed to 25° C. and stirred for 16 h. The temperature was raised to 50° C. and the mixture stirred for 4 h. The mixture was cooled to 25° C. and stirred for 3 days then treated with Rochelle’s salt (20 ml) and stirred for 1 h. The resultant solution was poured into water (30 ml) and extracted with EtOAc (3.x.40 ml). The combined organics were washed with brine, dried (MgSO4) and concentrated in vacuo. Purification by column chromatography on silica eluting with a 0-10percent MeOH/DCM gradient gave the title compound as a pale yellow solid (775 mg). deltaH (CDCl3, 400 MHz) 1.50 (2H, m), 2.21 (2H, d), 3.09 (1H, t), 3.58 (2H, m), 3.68 (1H, m), 4.51 (1H, d), 5.80 (1H, d), 6.25-6.40 (3H, m), 7.09 (1H, q), 7.12 (1H, s), 7.20 (1H, s), 10.72 (1H, br s). MS (ES): MH+ 289, (M-H+) 287.

The synthetic route of 33543-78-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Glaxo Group Limited; US2008/312209; (2008); A1;,
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 104619-51-4 as follows. Recommanded Product: Di(1H-imidazol-1-yl)methanimine

Di(imidazole-1-yl)methanimine (10.49 mmol, 1.69 g) was added to a solution of 2-amino-5-chlorophenol (3.50 mmol, 0.50 g) in acetonitrile (50 mL) with constant magnetic stirring. The reaction was then placed under argon atmosphere and gently refluxed for eight hours. The reaction was then concentrated under reduced pressure and silica gel column chromatography (3:1 hexanes/ethyl acetate) provided a crystalline white solid in an 86% yield.

According to the analysis of related databases, 104619-51-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Rynearson, Kevin D.; Charrette, Brian; Gabriel, Christopher; Moreno, Jesus; Boerneke, Mark A.; Dibrov, Sergey M.; Hermann, Thomas; Bioorganic and Medicinal Chemistry Letters; vol. 24; 15; (2014); p. 3521 – 3525;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 360-97-4,Some common heterocyclic compound, 360-97-4, name is 4-Amino-1H-imidazole-5-carboxamide, molecular formula is C4H6N4O, 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.

A mixture of 0.252 g 5-amino-1H-imidazole-4-carboxamide(Acros Organics, 2 mmol) and 0.874 g 5Cl-STB(2 mmol) in 10 cm3 MeOH was heated to reflux for 3 h.The reaction mixture was left at room temperature (24 h)and filtered. The formed solid was crystallized from 5 cm3MeOH to give 0.47 g (80 %) brown crystals of 3d. M.p.:[410 C; 1H NMR (500 MHz, DMSO-d6): d = 13.49 (s,broad, 2H, NH, C(20)-OH), 10.45 (s, 1H, C(40)-OH), 8.34(s, 1H, C(2)-H), 7.54 (s, 1H, C(60)-H), 6.66 (s, 1H, C(30)-H) ppm; 13C NMR (125 MHz, DMSO-d6): d = 165.0,157.5, 154.7, 134.8, 133.4, 130.3, 128.8, 120.5, 117.4,111.7, 103.4 ppm; MS (70 eV): m/z (%) = 295 (M?, 100),261 (14), 260 (15), 235 (13), 187 (19), 165 (7), 171 (14),153 (7), 69 (7).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Amino-1H-imidazole-5-carboxamide, its application will become more common.

Reference:
Article; Matysiak, Joanna; Skrzypek, Alicja; Niewiadomy, Andrzej; Juszczak, Malgorzata; Langner, Ewa; Lemieszek, Marta; Rzeski, Wojciech; Karpiska, Monika M.; Walczak, Katarzyna; Monatshefte fur Chemie; vol. 146; 8; (2015); p. 1315 – 1327;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 7189-69-7, name is 1,1′-Sulfonyldiimidazole, 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 7189-69-7, name: 1,1′-Sulfonyldiimidazole

NaH (60% in oil, 0.070g, 1.76mmol) was added to a stirred solution of compound 13 (0.23g, 0.16mmol) in dry DMF (3.5mL) at room temperature. After 1h, the suspension was cooled at -40C and 1,1?-sulfonyl-diimidazole (0.22g, 1.12mmol) in dry DMF (1.5mL) was added. After 24h the reaction mixture was quenched with MeOH and allowed to warm to room temperature, then diluted with water (40mL). The mixture was extracted with AcOEt (3×50mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and evaporated. Flash chromatography (hexane/AcOEt, 7:3) of the crude product gave trisaccharide 14 (0.21g, 85%) as an amorphous solid. [alpha]D20=+1.8 (c=1 in chloroform). 1H NMR (CDCl3): delta=7.94 (br s, 1H, Im), 7.53-7.10 (m, 45H, arom), 7.00 (m, 2H, Im), 5.46 (s, 1H, PhCH), 5.25-5.12 (m, 3H, H-1? and CH2Ph), 4.97 (d, 1H, J=11.1Hz, CH2Ph), 4.85-4.58 (m, 10H, H-1 and CH2Ph), 4.58-4.44 (m, 4H, H-2? and CH2Ph), 4.32 (d, 1H, J1?,2?=7.9Hz, H-1?), 4.23 (dd, 1H, J5?,6?=4.9Hz, J6a?,6b?=10.6Hz, H-6a?), 4.16-4.09 (m, 1H, CH2Ph), 4.09-3.80 (m, 5H, H-2, 3, 3?, 4?, 5?), 3.75-3.52 (m, 5H, H-a, 4, 5, 2?,4?), 3.52-3.20 (m, 7H, H-a?, c, c?, 6a?, 6b?, 3?, 6b?), 3.10-2.98 (m, 1H, H-5?), 1.91-1.69 (m, 2H, 2H-b), 1.29-1.21 (br d, 3H, 3H-6). 13C NMR (CDCl3): delta=155.6 (C=O), 139.1-136.5 (9C, arom), 136.8 (C Im),129.2-126.0 (46C, arom.), 118.6 (C Im), 101.4 (CHPh), 98.6 (C-1?), 98.2 (C-1), 97.1 (br s, C-1?), 85.7 (C-2?), 81.9 (C-4?), 80.3 (br s, C-4), 79.5 (C-3?), 79.2 (C-2?), 78.4 (br s, C-3), 76.7 (C-3?), 76.5 (br s, C-2), 76.2 (C-4?), 75.2 (2C, CH2Ph), 74.6 (br s, CH2Ph), 74.3 (CH2Ph), 73.6 (CH2Ph), 73.1 (br s, CH2Ph), 70.2 (C-5?), 68.4 (C-6?), 68.3 (C-5), 67.3 (C-6?), 67.2 (CH2Ph), 65.7 (C-5?), 65.2 (C-a), 50.8 and 50.5 (NCH2Ph), 44.6 and 43.7 (C-c), 28.4 and 27.9 (C-b), 18.0 (C-6). MS (ESI) m/z (%): 1550.3 (100) [M+NaM+Na]+. HRMS (ESI): m/z calcd for C88H93N3O19NaS 1550.6022 [M+Na]+, found 1550.6055

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, 1,1′-Sulfonyldiimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Morelli, Laura; Fallarini, Silvia; Lombardi, Grazia; Colombo, Cinzia; Lay, Luigi; Compostella, Federica; Bioorganic and Medicinal Chemistry; vol. 26; 21; (2018); p. 5682 – 5690;,
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 152628-03-0 as follows. category: imidazoles-derivatives

Stirring blade, a thermometer, three-neck flask 1L fitted with condenser, 4-methyl–2-n-propyl -1H- benzimidazole-6-carboxylic acid 50.0g (229mmol) and polyphosphoric acid added and stirred and 300 g, heated to around 70 C., the reaction solution obtained was stirred for 30 minutes, added in portions over a period N- methyl -O- phenylenediamine 45.0g of (368mmol) 2 hours It was.After adding the entire amount, stirring for 1 hour at around 70 C., and stirred for 5 h warmed to near yet 130. C..After confirming the disappearance of 4-methyl–2-n-propyl -1H- benzimidazole-6-carboxylic acid by HPLC, was cooled to about 70 C., while maintaining the water 600g The temperature of the reaction solution at 70 to 85 C. It was dropped little by little.After the total amount dropwise, 30 C. and cooled to near, pH of the reaction solution with aqueous ammonia was adjusted to be pH 8.3, after stirring for 1 hour warmed to around 50 C., the solid by vacuum filtration It is filtered off and washed the solid was filtered off with water 200g in the vicinity of 50 , to obtain a wet product of light brown crystals.Stirring blade, a thermometer, three-neck flask 1L fitted with condenser, was added and stirred the wet product of the resulting pale brown crystals and water 900 g, after stirring for 1 hour warmed to around 50 C. , vacuum filtered off the solids by filtration, wash the solid was filtered off with 100g of water around 50 C., the resulting wet product was dried for 15 hours under reduced pressure, a pale crude benzimidazole body as brown crystals to obtain a body 60.3g.The crude product of the benzimidazole body was analyzed by HPLC, the purity was 98.20%, the content of methyl benzimidazole body 0.14%, the content of ethyl benzimidazole body with 0.07% there were. stirring blade, a thermometer, three-necked flask 100mL fitted with a condenser, a mixture of a crude product 5.0g of methanol 12g and water 50g benzimidazole body obtained in Production Example 1 was added after stirring on, the addition of hydrochloric acid 2.1g containing hydrogen chloride 0.78 g (21.4 mmol), stirred for 10 minutes at about 25 C., the solid in the reaction solution was confirmed to be dissolved.Then, was added aqueous ammonia 1.1g containing ammonia 0.28 g (16.5 mmol), precipitation of white crystals was confirmed.After stirring for 1 hour at about 25 C., vacuum filtered through the solid was filtered off, the solid was filtered off with water 5g were washed twice and dried for 12 hours at 60 C. under reduced pressure and the resulting wet biomass, to obtain a benzimidazole body 4.2g (13.9mmol) as white crystals.Recovery rate, which is calculated based on the mass of the crude product of the benzimidazole body was 84.4%.As a result of the benzimidazole body obtained was analyzed by HPLC, the purity was 99.56%, the content of methyl benzimidazole body 0.06%, the content of ethyl benzimidazole body 0.02% met.

According to the analysis of related databases, 152628-03-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TOKUYAMA CORPORATION; MIYAOKU, TAKAYUKI; (16 pag.)JP2015/160810; (2015); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 68282-47-3, name is 2-Phenyl-1H-imidazole-4-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 68282-47-3, Computed Properties of C10H8N2O

Reference Example 14 1-[(2,6-difluorophenyl)sulfonyl]-2-phenyl-1H-imidazole-4-carbaldehyde To a solution of 2-phenyl-1H-imidazole-4-carbaldehyde (1.00 g) in tetrahydrofuran (70 mL) was added sodium hydride (60% in oil, 348 mg) at room temperature, and the mixture was stirred for 30 min. 2,6-Difluorobenzenesulfonyl chloride (1.36 g) was added to the reaction mixture, and the mixture was stirred for 1.5 hr. Water was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was crystallized from diethyl ether to give the title compound as colorless crystals (yield 1.36 g, 67%). 1H-NMR (CDCl3) delta: 6.82-6.91 (2H, m), 7.27-7.46 (5H, m), 7.51-7.60 (1H, m), 8.38 (1H, s), 9.98 (1H, s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Phenyl-1H-imidazole-4-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2005957; (2008); A1;,
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 147403-65-4 as follows. Application In Synthesis of Methyl 2-ethoxy-1-((2′-(N-hydroxycarbamimidoyl)-[1,1′-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate

Example 2Preparation of methyl l-[[2′-(4, 5-dihydro-5-oxo-4H-l, 2, 4-oxadiazol-3-yl) biphenyl- 4-yl] methyl]-2-ethoxy-lH-benzimidazole-7-carboxyIate To a solution of methyl 2-ethoxy [[2′-(hydroxyamidino) biphenyl-4-yl] methyl]- lH-benzimidazole-7-carboxylate (25 g) in tetrahydrofuran (700 ml), N,N- carbonyldi imidazole (15 g) and l,8-diazabicyclo[5.4.0]undec-7-ene (DBU)(13 g) was added and resulting solution was stirred for 30-40 mins. at about 20-25C. To the resulting solution ethyl acetate (700 ml) and saturated solution of sodium bisulphite (700 ml) was added. Organic layer was separated, washed with brine solution and evaporated under vacuum to concentrate the solution. Reaction mass was cooled to 20-25C and cyclohexane was added to it and the solution was stirred for about 20-25C. Product was filtered and dichloromethane was charged to it followed by stirring. The product was filtered, washed and dried to obtain title compound. (Yield: 17.8 g; 68% (Purity: 96% with desethyl impurity 0.1 1%)

According to the analysis of related databases, 147403-65-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JUBILANT LIFE SCIENCES LIMITED; BANSAL, Deepak; MISHRA, Himanchal; DUBEY, Shailendr, Kumar; CHOUDHARY, Alka, Srivastava; VIR, Dharam; AGARWAL, Ashutosh; WO2012/107814; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 53439-88-6, These common heterocyclic compound, 53439-88-6, name is 5-Amino-1,3-dimethyl-1H-benzo[d]imidazol-2(3H)-one, 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 0 C. solution of 5-amino-1,3-dimethyl-1H-benzo[d]imidazol-2(3H)-one (4 g, 22.6 mmol) in 25 mL of CHCl3 and 25 mL of AcOH was slowly added dropwise bromine (3.5 g, 22.6 mmol). The mixture was stirred at RT for 30 min, then concentrated and purified by silica gel chromatography (1:1 EtOAc/hexanes) to afford 5-amino-6-bromo-1,3-dimethyl-1H-benzo[d]imidazol-2(3H)-one as a yellow solid (3.2 g, 69%). MS (ES+) C9H10BrN3O requires: 256. found: 257 [M+H]+.

The synthetic route of 53439-88-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Board of Regents, The University of Texas System; Palmer, Wylie; Jones, Philip; Liu, Gang; Petrocchi, Alessia; Reyna, Naphtali; Subrumanian, Govindan; Theroff, Jay; Yau, Anne; (114 pag.)US2016/60260; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem