Author: Jessica.F

Synthetic Route of 45676-04-8, A common heterocyclic compound, 45676-04-8, name is 1-tert-Butylimidazole, molecular formula is C7H12N2, 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.

1.2.7) 3-tert-Butyl-1-[(tert-butyl(methyl)phosphinooxy)methyl]imidazolium tosylate 15 In a Schlenk tube with pressure release valve, 1.00 g (3.3 mmol) of tert-butyl(methyl)-(tosylmethyl)phosphine oxide (14) and 0.45 g (3.6 mmol) of N-tert-butylimidazole (1) were stirred in 0.7 ml of toluene at 105 C. for 72 hours. The red-brown, viscous oil was precipitated from 10 ml of hexane in an ultrasound bath.

The synthetic route of 45676-04-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF SE; US2010/317866; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 2963-77-1, 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. 2963-77-1, name is 4-(1H-Benzo[d]imidazol-2-yl)aniline belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Oxalyl chloride (191 muL) was added to a solution of 1-methyl-1H-pyrazole-5-carboxylic acid (200 muL) in DCM (2 mL) and DMF (1 drop). After 1 hour, the reaction mixture was evaporated. A solution of 4-(1H-benzo[d]imidazol-2-yl)aniline (166 mg) and triethylamine (420 muL), in DCM (4 mL) was added to the initial reaction residue and stirred at ambient temp for 1 hour. The Reaction mixture was diluted with DCM and extracted sequentially with sat bicarb, water, brine, then dried over sodium sulfate, filtered and evaporated. The bis acylated material was purified on silica, eluting with a gradient of ethyl acetate (50-100%) in hexane. The pure bis acylated material was treated with ethylamine solution (2M in THF, 5 mL) for 18h. The reaction mixture was evaporated. Trituration with ethyl acetate / diethyl ether [1:4], afforded a solid which was collected by filtration (77mg, Y = 30%). UPLC-MS (Acidic Method, 4 min): rt 1.05 min, m/z 318.1 [M+H]+ 1H NMR (400 MHz, DMSO-d6) d ppm 12.83 (br s, 1H), 10.41 (s, 1H), 8.13-8.21 (m, 2H), 7.92 (d, J=8.8 Hz, 2H), 7.64 (br d, J=5.9 Hz, 1H), 7.56 (d, J=2.0 Hz, 1H), 7.52 (br d, J=6.4 Hz, 1H), 7.19 (br d, J=4.3 Hz, 2H), 7.11 (d, J=2.0 Hz, 1H), 4.11 (s, 3H).

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, 4-(1H-Benzo[d]imidazol-2-yl)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JAGUAHR THERAPEUTICS PTE LTD; METE, Antonio; HITCHIN, James, R.; GRAHAM, Mark; (46 pag.)WO2020/43880; (2020); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 14741-71-0, name is Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate, 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. COA of Formula: C11H12N2O2

Step 4: 4-Amino-3-benzimidazol-2-yl-6-(4-methylpiperazinyl)hydroquinolin-2-one Ethyl 2-benzimidazol-2-ylacetate (1.1 equivalents) and 2-amino-5-(4-methylpiperazinyl)benzenecarbonitrile (1.0 equivalent) were dissolved in 1,2-dichloroethane, and then SnCl4 (11 equivalents) was added. The mixture was heated at reflux overnight. Upon cooling, the mixture was concentrated in vacuo. NaOH (3 M) was added to the solid, and the mixture heated at 80 C. for 0.5 hours. The solid was filtered and washed sequentially with H2O, CH2Cl2, and acetone. LC/MS indicated that the product was present in the acetone layer and the solid. These fractions were combined and purified by silica gel chromatography (5-10% MeOH in CH2Cl2 with 1% Et3N) to give the desired product. LC/MS m/z 375.4 (MH+), Rt 1.65 minutes.

The synthetic route of Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHIRON CORPORATION; US2005/256157; (2005); A1;; ; Patent; Chiron Corporation; US2005/261307; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 305790-48-1, 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. 305790-48-1, name is 6-Bromo-1-methyl-1H-benzo[d]imidazol-2(3H)-one belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 8 6-(3-chloro-phenyl)-1-methyl-1,3-dihydro-benzoimidazol-2-one Prepared from 1-methyl-6-bromo-1,3-dihydro-benzoimidazol-2-one and 3-chloro-phenyl boronic acid in the same fashion as that of Example 5. mp 219-220 C.; 1H-NMR (DMSO-d6) delta11.0 (s, 1H), 7.75 (bs, 1H), 7.65 (dd, 1H, J=7.5, 1.76 Hz), 7.49-7.44 (m, 2H), 7.39-7.32 (m, 2H), 7.06 (d, 1H, J=7.94 Hz), 3.35 (s, 3H); MS (ES) m/z 259([M+H]+, 100%); Anal. Calc. For C14H11ClN2O: C, 65; H, 4.29; N, 10.83. Found: C, 64.44; H, 4.36; N, 10.6.

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, 6-Bromo-1-methyl-1H-benzo[d]imidazol-2(3H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; American Home Products Corporation; Ligand Pharmaceuticals, Inc.; US6380235; (2002); B1;,
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

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

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. 10351-75-4, name is 1H-Benzo[d]imidazole-5,6-dicarboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1H-Benzo[d]imidazole-5,6-dicarboxylic acid

Step A: 5,6-di-(methoxycarbonyl)-benzimidazole To a solution of 200 mg of 5,6-benzimidazoledicarboxylic acid dissolved in 2.0 mL of MeOH and 2.0 mL of diethyll ether was added 4 mL of trimethylsilyldiazomethane [2.0 M in hexanes]. The resulting solution was stirred for 1 hour before dilution with 20 mL of H2O and extraction with 2*10 mL of EtOAc. the organic phases were dried over MgSO4 and concentrated under reduced pressure. Column chromatography (SiO2, 5% MeOH in CH2Cl2) yielded 210 mg of the title compound as a yellow oil. Mass Spectrum (ESI) 231 (M+1).

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 10351-75-4.

Reference:
Patent; Merck & Co., Inc.; US6498165; (2002); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 1219741-21-5,Some common heterocyclic compound, 1219741-21-5, name is 5-Chloro-6-iodo-1H-benzo[d]imidazole-2(3H)-thione, molecular formula is C7H4ClIN2S, 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.

K2C03 (0.22 g, 1.61 mmol), followed by iodomethane (0.1 mL, 1.61 mmol), was added to a solution of 5-chloro-6-iodo- 1,3- dihydro-2H-benzimidazole-2-thione (1 g, 3.22 mmol) in acetone (20 mL) at 0C. The reaction was stirred at rt for 1 h. Additional K2C03 (1. 1 mmol) and iodomethane (1. 1 mmol) were added. The reaction was stirred at rt overnight, then the volatiles were removed and the residue was partitioned between EtOAc and water. Concentration of the EtOAc layer afforded the desired product as a white foam, which was used in the next step without further purification.

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; JIANG, Jinlong; KASSICK, Andrew, J.; KEKEC, Ahmet; SEBHAT, Iyassu, K.; WO2011/106273; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 98873-55-3, name is 2-(1H-Imidazol-1-yl)acetonitrile, 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 98873-55-3, Formula: C5H5N3

The cyanomethyl imidazole (5.0 g, 20 mmol) was alkylated using NaH (1.2 g, 60% in oil, washed with hexanes) and iodononane (7.6 g, 30 mmol) as described in Example 5, the General Procedure for the nucleosides. The products were purified by FC using a gradient of ethyl acetate in hexanes (20 to 50%). Evaporation of the fractions containing the products yielded methyl 5-(cyano[nonyl]methyl)-3-tetrahydropyranyl-imidazole-4-carboxylate (5.0 g, 67%) as a yellow foam. 1 H-NMR (200 mHz): 67,8.22 (s, 1H, H-2); 5.87 (m, 1 H, H-2′ tetrahydropyranyl); 4.58 (m, 1H, methene); 3.85 (s, 3H, COOCH3); 1.30 and 0.88(2 m, 19H, nonyl). Anal. Calcd for C21 H33 N3 O3 (375.51): C, 67.17; H, 8.86;N, 11.19. Found: C, 67.47; H, 8.95;N, 11.21.

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, 2-(1H-Imidazol-1-yl)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ISIS Pharmaceuticals, Inc.; US5457191; (1995); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem