Month: July 2021

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

Synthetic Route of 39070-14-9,Some common heterocyclic compound, 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, molecular formula is C5H7N3O3, 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 Compound i (1 g) in DMF (15 mL) was added N- bromosuccinimide (NBS, 1.25 g) and the reaction mixture stirred at 600C for 3h. Then the reaction mixture was diluted with brine, extracted with EtOAc, dried and concentrated to yield a residue that was separated by column chromatography using 0 – 80% EtOAc/Hexanes to yield Compound ii (1.3 g).

The synthetic route of 39070-14-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THRESHOLD PHARMACEUTICALS, INC.; CHEN, Tao; WO2008/151253; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 53484-16-5,Some common heterocyclic compound, 53484-16-5, name is 6-Bromo-1-methyl-1H-benzo[d]imidazole, molecular formula is C8H7BrN2, 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 intermediate 5 (2.5g, 11.8 mmol) in dioxane (100ml) were addedtributyl(vinyl)tin (5,2ml, 18 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.69g, O.Smmol) and the mixture was heated under reflux for 24 hours and then concentrated under reduced pressure. The residue was purified by chromatography on silica gel, eluting with CH2CI2/MeOH (95/5). The title compound was obtained as an oil (1.8g, 96.1percent); NMR H1 (300MHz, CDCI3, ppm) 5: 7.9 (s, 1H), 7.75 (d, 1H), 7.4 (m, 2H), 6.85 (dd, 1H), 5.8 (d, 1H), 5.25 (d, 1H), 3.85 (s, 3H).

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

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2004/111046; (2004); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 73746-45-9, A common heterocyclic compound, 73746-45-9, name is 5-Iodo-2-methyl-1H-imidazole, molecular formula is C4H5IN2, 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 160 mg (1.11 mmol) of 5-chloro-2-methyl-2H-pyridazin-3-one (CAS: [14628- 34-3]), 230 mg (1.11 mmol) of 4-iodo-2-methyl-lH-imidazole (CAS: [73746-45-9]), in 3.5 ml of dry DMF were added 721 mg (2.21 mmol) of cesium carbonate. The suspension was stirred for 30 min at 45C, then for 3h at 65C and allowed to cool. The cristallised product is filtered off, washed with ethyl acetate and dried in vaccuo to yield 250 mg (0.791 mmol, 71%) of the title compound as a crystalline light yellow solid, MS: m/e = 316.9 (M+H+).

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; F. HOFFMANN-LA ROCHE AG; JAESCHKE, Georg; LINDEMANN, Lothar; VIEIRA, Eric; WICHMANN, Juergen; WO2011/6910; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 75370-65-9,Some common heterocyclic compound, 75370-65-9, name is 4-Amino-1H-benzo[d]imidazol-2(3H)-one, molecular formula is C7H7N3O, 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.

Amine 2c (500 mg, 1.9 mmol) was dissolved in 20ml of AcOEt and at 0C triphosgene (580 mg, 2 mmol) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 5ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound la (265 mg, 1.78 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt 9.5 / MeOH 0.5). The solvent was evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1 X 20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 140 mg of a pale yellow solid. Yield = 18% ‘HNMR (DMSO, 400 MHz) delta 1.54 (2H, m), 1.68 (4H, m), 2.85 (4H, m), 4.42 (2H, d, J = 6 Hz), 6.63 (1H, d, J = 7.6 Hz), 6.76 (1H, t), 6.84 (1H, t, J = 8.4 Hz), 6.95 (1H, d, J = 8.4 Hz), 7.31 (1H, s), 7.41 (1H, d), 7.52 (1H, d, J = 8.4 Hz), 8.33 (1H, s), 10.01 (1H, bs), 10.60 (1H, bs); [M+1] 434.1 1 (C2iH22F3N5O2 requires 433.43).

The synthetic route of 75370-65-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMESTE S.R.L.; NAPOLETANO, Mauro; TREVISANI, Marcello; PAVANI, Maria Giovanna; FRUTTAROLO, Francesca; WO2011/120604; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem