Category: imidazoles-derivatives

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. 3034-62-6, name is 2-Iodo-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-Iodo-1H-imidazole

The organic material was extracted with ethyl ether, washed with 10% aqueous NaS2 O3, brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (hexanes/ethyl acetate=3:2) to give the title compound as a light yellow oil (639 mg, 37%) and the corresponding 2-iodoimidazole as a light yellow solid (245 mg, 14%). PNMR (CDCl3, 300 MHz): d 2.89 (s, 6H) 7.34 (s, 1H), 7.78 (s, 1H).

According to the analysis of related databases, 3034-62-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Allergan, Inc.; US5475113; (1995); 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 71759-89-2 as follows. Recommanded Product: 5-Iodo-1H-imidazole

A mixture of 16 (150 mg, 0. 298 mmol), 4-IODOIMIDAZOLE (86.7 mg, 0.447 mmol), dichlorobis (triphenylphosphine) palladium (II) (20.9 mg, 0.0298 mmol), LiCl (37.9 mg, 0. 894 MMOL) 9 M AQ. NA2CO3 (0.75 mL, 0.75 mmol) in toluene (1.8 ML) and EtOH (1. 8 ML) was microwaved at 120 C for 15 min. The reaction mixture was cooled, brine (3 mL) was added and the aqueous layer extracted with ethyl acetate (3 X 5 ML). Sorbent (HM-N, Jones Chromatography) was added, the solvent evaporated and the product purified by silicagel chromatography using MEOH : CH2CL2 (3: 97) (gradient elution) to give product 17 as A brown foam (111 mg, 84%); 1H NMR (400 MHz, CDCl3) 62. 96 (s, 6H), 6.77 (d, J = 8. 8 Hz, 2H), 7.48-7. 35 (m, 5H), 7.52 (t, J = 7. 6 Hz, 1H), 7.81 (s, 1H), 7.99 (s, 1H), 8. 11 (d, J = 7.5 Hz, 2H), 8. 27 (d, J = 2.0 Hz, 1H), 8.61 (d, J = 2. 1 HZ, 1H).

According to the analysis of related databases, 71759-89-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EISAI LONDON RESEARCH LABORATORIES LIMITED; WO2004/78756; (2004); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 2302-25-2, name is 4-Bromo-1H-imidazole, 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. Computed Properties of C3H3BrN2

A mixture of 4-bromo-lH-imidazole (223 mg, 1.52 mmol), 4- fluorophenylboronic acid (425 mg, 3.03 mmol), copper (II) acetate (413 mg, 2. 28 mmol), pyridine (0.25 mL) and powdered 4A molecular sieves (1 g) in 1,2-dichloroethane (7mL) was stirred at room temperature under a slow stream of air for 44 hours. The reaction mixture was filtered through Celite (D, washing with ethyl acetate. The filtrate was concentrated and the residue purified by flash column chromatography on silica eluting with 10 to 20% ethyl acetate/isohexane to give the product as a white solid (135 mg, 37%). 8 (iH, 400MHz, CDCl8) 7.16-7. 22 (3H, m), 7.32-7. 37 (2H, m), 7.65 (1H, d, J = 1.5 Hz). MS (ES+) 241,243 ([MH]+).

The synthetic route of 4-Bromo-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; WO2003/93252; (2003); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 2620-76-0, 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 2620-76-0 as follows.

A four-neck, 500 mL round bottom flask equipped with a top stirrer, nitrogen inlet, 125 mL addition funnel, and thermocouple was rinsed with dry nitrogen for 10 minutes. The flask was charged with 2-(4-bromophenyl)-1-phenyl-1H-benzo[d]imidazole (25.0 g, 71.59 mmol) and THF (250 mL), and the reaction was cooled to an internal temperature of -71V. 1.6 ME butyllithium (67 mL, 107.2 mmol) in hexane was added dropwise via an addition funnel over 30 minutes, and an additional 30 min was stirred at -72 °C. Add 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-di|1B boron boron by adding funnel (out 0 parent 31301>013116) (32 1111 ^, 171.99 mmol) to a deep red solution for 30 minutes, keeping the temperature below -70t. Remove the cold bath and allow the yellow slurry to warm to room temperature and mix for 16 h. The reaction was concentrated by rotary evaporation, then dissolved in dichloromethane (350 mL) and washed with water (200 mL) to form a cloudy mixture. The aqueous layer was extracted with dichloromethane (2 chi 150 mL) and the combined organic layers dried over EtOAc EtOAc EtOAc The resulting yellow solid was washed with hexanes (100 mL) which removed most of the color to afford 22.2 g of light brown solid. The solid was separated into two portions and recrystallized from EtOAc (EtOAc: EtOAc: EtOAc: EtOAc:

According to the analysis of related databases, 2620-76-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DOW GLOBAL TECHNOLOGIES LLC; ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.; WELSH, DEAN M.; ONDARI, MARK E.; GRAY, KAITLYN; KIM, BONG-OK; CHEE, MOO-KEUN; FROESE, ROBERT D.; (60 pag.)TWI631109; (2018); B;,
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. 71759-88-1, name is 5-Iodo-1-methyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 71759-88-1

[2637] EtMgBr (3Molar in Et2O) solution (791 uL), was dripped into a solution of 914 (0.518 g, 3.15 mmol, 6 eq.) in ClCH2CH2Cl (6 ML), for 30 minutes. To the white suspended mixture, 913b (0.280 g, 0.525 mmol) was then added and stirred at 60 C. for 3 hours. Reaction was treated with saturated NH4Cl at 0 C. by pouring the reaction into the cold NH4Cl. Extracted with Ethyl Acetate, dried over MgSO4 and evaporated to dryness. Column Chromatography (SiO2), eluted with 1%, 2% & 3% MeOH/CH2Cl2 gave 0.054 g of compound 918.

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 71759-88-1.

Reference:
Patent; Schering Corporation; US2004/122018; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 6160-65-2, These common heterocyclic compound, 6160-65-2, name is 1,1′-Thiocarbonyldiimidazole, 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 solution of 3-[4-(-mercapto-5-methoxy-benzimidazole-1-sulfonyl)- [PHENOXY]-2,] 2-dimethyl-propionic acid methyl ester (Intermediate A39,16. 1 g, 0.0395 mol) in pyridine (200 mL) was added 1,1′-thiocarbonyldiimidazole (10.56 g, 0.0592 mol). The reaction mixture was stirred at room temperature overnight and then water was added (2.5 L). After stirring for 1 hr, the solid was collected, washed with water (3 L), and dried to give 16.5 g (93%) of the title compound, benzimidazolethiol as a tan solid.

Statistics shows that 1,1′-Thiocarbonyldiimidazole is playing an increasingly important role. we look forward to future research findings about 6160-65-2.

Reference:
Patent; GARST, Michael, E.; SACHS, George; SHIN, Jai, Moo; WO2004/9583; (2004); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 401567-00-8, name is 2-Chloro-1H-benzo[d]imidazole-5-carbonitrile, 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 401567-00-8, Recommanded Product: 401567-00-8

General procedure: A mixture of 10 (345 mg, 0.853 mmol), 2,5-dichlorobenzimidazole (11a) (191 mg, 1.02 mmol) and N,N-diisopropylethylamine (0.18 mL, 1.0 mmol) in N-methyl-2-pyrrolidone (6 mL) was stirred at 100 C overnight. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with brine, dried and concentrated under reduced pressure. The residue was purified by high performance liquid chromatography to give 3-{(2S,4S)-1-benzyloxycarbonyl-4-[4-(5-chlorobenzimidazol-2-yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl}thiazolidine (122 mg, 26%) as a pale-yellow powder.A mixture of the above compound (110 mg, 0.198 mmol) and 30% hydrogen bromide-acetic acid solution (10 mL) was stirred at room temperature for 6 h. Diethyl ether was added to the reaction mixture, and the precipitate was collected by filtration and recrystallized with ethanol to give the title compound (56 mg, 40%) as a white powder.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-1H-benzo[d]imidazole-5-carbonitrile, and friends who are interested can also refer to it.

Reference:
Article; Yoshida, Tomohiro; Akahoshi, Fumihiko; Sakashita, Hiroshi; Sonda, Shuji; Takeuchi, Masahiro; Tanaka, Yoshihito; Nabeno, Mika; Kishida, Hiroyuki; Miyaguchi, Ikuko; Hayashi, Yoshiharu; Bioorganic and Medicinal Chemistry; vol. 20; 16; (2012); p. 5033 – 5041;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 54624-57-6, 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. 54624-57-6, name is 2-Bromobenzimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step 1: Preparation of intermediate benzyl 2-bromo-1H-1,3-benzodiazole-1-carboxylate (7a) Under nitrogen atmosphere, benzyl chloroformate (0.174 mL, 1.218 mmol) was added to a solution of 2-bromo-1H-1,3-benzodiazole (200 mg, 1.015 mmol) and pyridine (0.123 mL, 1.523 mmol) in anhydrous dichloromethane (4 mL) at 0°C. The reaction mixture was stirred at room temperature for 3 hours, then cooled to 0°C. Water (5 mL) was added, and once at room temperature, the aqueous layer was extracted with dichloromethane (2 x 7 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by preparative TLC (cyclohexane/ethyl acetate: 80/20) to provide benzyl 2-bromo-1H-1,3-benzodiazole-1-carboxylate (7a) (250 mg, 0.755 mmol, 74percent). 1H NMR (400 MHz, CDCl3) d 5.54 (s, 2H), 7.30-7.37 (m, 2H), 7.39-7.48 (m, 3H), 7.50-7.55 (m, 2H), 7.64-7.71 (m, 1 H), 7.85-7.92 (m, 1H).

The synthetic route of 2-Bromobenzimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LABORATOIRE BIODIM; Ledoussal, Benoit; Le Strat, Frederic; Chasset, Sophie; EP2821104; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 2620-76-0, A common heterocyclic compound, 2620-76-0, name is 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, molecular formula is C19H13BrN2, 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.

In a glovebox, three oven-dried reaction jars were each charged with 2-(4- bromophenyl)-l -phenyl- lH-benzimidazole 12 (4.20 g, 12.0 mmol), bis(pinacolato)- diboron (Bpin) (3.05 g, 12 mmol, 1 eq.), potassium acetate (2.95 g, 30 mmol, 2.5 eq.), and Pd(dppf)Cl2 (300 mg, 0.36 mmol, 3 mol%). The solvent (1,4-dio-xane, 80 mL) was added to each jar and the reactions were stirred at 80 C overnight. After complete conversion (-95%) as determined by LC-MS, the contents of the reaction jars were mixed and the solvent removed under reduced pressure. Water (200 mL) was added the product was extracted into chloroform (3×200 mL), the product was passed through a silica plug and recrystallized from acetonitrile. The reaction was successfully scaled up to 12 g in 90% yield after recrystallization to give the desired boronic ester 8 at -98% purity as judged by LC-MS and NMR. *H NMR (500 MHz, cdcl3) delta 7.90 (dt, J = 8.1, 0.9 Hz, 1H), 7.76 – 7.71 (m, 2H), 7.60 – 7.55 (m, 2H), 7.49 – 7.41 (m, 3H), 7.35 – 7.21 (m, 6H), 1.32 (s, 12H); 13C NMR (126 MHz, CDC13) delta 172.37, 157.10, 152.56, 135.25,133.58, 133.11, 131.25, 130.46, 128.49, 128.13, 128.03, 127.96, 127.73, 127.11, 126.47, 125.24, 124.99, 123.30

The synthetic route of 2620-76-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DOW GLOBAL TECHNOLOGIES LLC; ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.; ONDARI, Mark E.; WELSH, Dean M.; FROESE, Robert DJ; NA, Hong-Yeop; (38 pag.)WO2016/209895; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 2620-76-0,Some common heterocyclic compound, 2620-76-0, name is 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, molecular formula is C19H13BrN2, 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 1.3.3; 10; [0087] l-phenyl-2-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl)- lH-benzo[d] imidazole (10): A mixture of Compound 9 (0.70 g, 2 mmol), bis(pinacolate)diborane (0.533 g, 2.1 mmol), l,l’-Bis(diphenylphosphino)ferrocene] dichloropalladium (Pd(dppf)Cl2) (0.060 g, 0.08 mmol) and anhydrous potassium acetate (0.393 g, 4mmol) in 1,4-dioxane (20 mL) was heated at 800C under argon overnight. After cooling to r.t., the whole mixture was diluted with ethyl acetate (80 mL) then filtered. The solution was absorbed on silica gel, then purified by column chromatography (hexanes/ethyl acetate 5:1 to 3:1) to give a white solid (Compound 10) (0.64 g, in 81% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, its application will become more common.

Reference:
Patent; NITTO DENKO CORPORATION; ZHENG, Shijun; CAYAS, Jensen; LI, Sheng; MOCHIZUKI, Amane; CHAF, Hyunsik; HARDING, Brett, T.; WO2011/8560; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem