Category: imidazoles-derivatives

Electric Literature of 615-15-6,Some common heterocyclic compound, 615-15-6, name is 2-Methyl-1H-benzo[d]imidazole, molecular formula is C8H8N2, 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.

General procedure: A 50 mL Schlenk tube equipped with a stirrer bar was charged with KI (16.6 mg, 0.1 mmol), benzotriazole (59.5 mg, 0.5 mmol), DMA (2 mL), and K2S2O8 (270 mg, 1 mmol) under air. The mixture was then stirred at 80 C for 6 h (TLC monitoring), poured into H2O (20 mL), and extracted with EtOAc (3 ×). Then the organic phase was evaporated under vacuum, and the crude product was purified by column chromatography [silica gel, PE-EtOAc (10:1 to 2:1)] to give a colorless oil; yield: 98 mg (96%);

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

Reference:
Article; Zhu, Zheng; Wang, Yufeng; Yang, Mingmeng; Huang, Ling; Gong, Jiuhan; Guo, Shengmei; Cai, Hu; Synlett; vol. 27; 19; (2016); p. 2705 – 2708;,
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. 16681-59-7, name is 2-Bromo-1-methyl-1H-imidazole, A new synthetic method of this compound is introduced below., Safety of 2-Bromo-1-methyl-1H-imidazole

A solution of 1 mmol (0.167 g) of carbazole, 2 mmol (0.322 g) of 2-bromo-N-methyl-imidazole, benzotriazole 40 mol% (0.046 g) 20 mmol% (0.038 g) of copper iodide and 1.4 mmol (0.157 g) of potassium tertiary-butoxide were stirred in 6 mL of dimethylsulfoxide at 135C for 48 hours. The reaction mixture was allowed to cool and then water was added and extracted with ethyl acetate. The ethyl acetate extract was dried over magnesium sulfate and then distilled under reduced pressure. The resulting brown solid was purified by silica column chromatography (using ethyl acetate and hexane). Finally, a colorless solid ligand 12 was obtained. The yield of the ligand 12 was 40%.

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; Samsung Electronics Co., Ltd.; Samsung SD I Co., Ltd.; Das, Rupa Sri Rajini; Lee, Gang Mun; Noh, Chang Ho; Bae, Hay Jin; Rai, Birendra Kumar; Kravtsuk, Dmitry; (49 pag.)KR2016/12890; (2016); A;,
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. 53484-16-5, name is 6-Bromo-1-methyl-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., Application In Synthesis of 6-Bromo-1-methyl-1H-benzo[d]imidazole

3.1. Compound A 2-[4-[(3-methylbenzimidazol-5-yl)amino]phenyl]acetonitrile j00313j A mixture of Pd2(dba)3 (0.01 mmol) and Xantphos (0.01 mmol) in 1,4-dioxane (1 mL) was sonicated and added under nitrogen to a mixture of 6-bromo- 1 -methyl-benzimidazole (0.45 mmol), 2-(4-aminophenyl)acetonitrile (0.58 mmol) and Cs2CO3 (0.62 mmol) in 1,4-dioxane (2 mL). The mixture was stirred at 110°C for 12 h. The mixture was diluted (DCM), washed (H20), dried (phase separator and concentrated. The residue was purified by prep HPLC to yield the desired product (Compound A).j00314j MW: 262.3. MS Ms?d: 263.2.j00315j NMR: 1HNMR (400 MHz, DMSO-d6): = 8.13 (1 H, s), 7.68(1 H, dd), 7.60(1 H, dd), 7.54 (1 H, d), 7.32 (1 H, d), 7.24 (1 H, t), 6.91 (1 H, dd), 3.77 (3 H, s), 3.39 (3 H, s).

The synthetic route of 53484-16-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GALAPAGOS NV; MENET, Christel, Jeanne, Marie; MAMMOLITI, Oscar; BLANC, Javier; OR?ULIC, Mislav; RO?CIC, Maja; WO2015/110378; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 288-32-4, A common heterocyclic compound, 288-32-4, name is 1H-Imidazole, molecular formula is C3H4N2, 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.

a. 4-(1H-Imidazol-1-yl)-nitrobenzene To a solution of 4-fluoronitrobenzene (25 g; ~0.18 mol) in 250 ml N,N-dimethylformamide was added imidazole (50 g; ~0.74 mol). The reaction mixture was stirred at 140 C. for 2 h, and then poured into ice-water to give the title compound as a precipitate. Yield: 32 g (~94%). M.p. 199-202 C.

The synthetic route of 288-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Novo Nordisk A/S; US5532236; (1996); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 16681-56-4, 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. 16681-56-4, name is 2-Bromo-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows.

In a 10 mL vial was added N-(2,4-dimethyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan- 2-yl)phenyl)-4-(pyridin-2-ylmethoxy)benzamide (0.25 g, 0.55 mmol), 2-bromo-lH-imidazole (0.120 g, 0.82 mmol), and Cs2CO3 (0.444 g, 1.36 mmol) in dioxane (5 mL) to give a brown suspension. The reaction mixture was diluted with water (2 mL). Nitrogen was bubbled in for 20 min before Pd(PPh3)4 (0.063 g, 0.05 mmol) was added. The reaction was heated at 110 0C for 4h under microwave conditions. The reaction mixture was concentrated under reduced pressure. The residue was purified by Gilson HPLC (MeCN/0.1% TFA in water). To the purified product was added HCl in Et2O (0.5 mL, 1 mmol) . The mixture was concentrated in vacuo to give the HCl salt of the title compound (10 mg, 4.2%). 1H NMR (DMSO-d6) delta 2.31 (s, 3 H), 2.36 (s, 3 H), 5.32 (s, 2 H), 7.18 (d, 2 H), 7.39 (s, 1 H), 7.45 ( br s, 1 H), 7.61 (s,2 H), 7.84 (s, 2 H), 7.96 (m, 3 H), 8.63 (d, 1 H), 9.90 (s, 1 H), 14.54 ( br s, 1 H). MS (M+H+) = 399.

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-1H-imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/27746; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 147403-65-4, A 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, 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.

Example 2 Methyl 2-ethoxy- 1 -((2′-((hydroxyamino)iminomethyl)biphenyl-4-yl)methyl)- 1 H-benzo [d] – imidazole-7-carboxylate (la) – modification of the process (US 5,583,141 ; EP 0,520,423)The product obtained using the method of Example 1 (3.9 g) was dissolved in dichloromethane (400 ml) and the resulting, still turbid solution was washed with 4 x 50 ml of 5 % HC1. Thus obtained aqueous solution was alkalinized with a concentrated (20 %) solution of sodium hydroxide and the resulting precipitate was aspirated and washed with water. After drying 1.6 g (the total yield of Example 1 and Example 2 is 36.0 %) of the substance (la) were obtained, containing, according to HPLC, 96.7 % of the product (la), an undetectable amount of the starting nitrile (IVa) and 1.3 % of the desethyl nitrile (Via).

The synthetic route of 147403-65-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZENTIVA, K.S.; RADL, Stanislav; WO2012/119573; (2012); A1;,
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. 16681-56-4, name is 2-Bromo-1H-imidazole, A new synthetic method of this compound is introduced below., name: 2-Bromo-1H-imidazole

2-Bromo-lH-imidazole (100 mg, 0.680 mmol) was dissolved in DMF (2 mL) in a microwave vial in an ice bath and purged with nitrogen for 10 min. With the solution at 0 C, sodium hydride (60% dispersion in mineral oil) (62.6 mg, 1.565 mmol) was added and the solution was stirred for 10 min under nitrogen. A solution of 2-(bromomethyl)pyridine hydrobromide (207 mg, 0.816 mmol) in DMF (2 mL) was added dropwise to the reaction mixture. Once all reagents were added, the reaction mixture was allowed to warm to RT and stirred for 2 days under an atmosphere of nitrogen. The solvent was removed under reduced pressure. The crude product was dissolved in ethyl acetate (20 mL) and washed with brine (20 mL). The solvent was again removed from the organic layer under reduced pressure. The samples were dissolved in 1: 1 MeOH:DMSO (3 mL) and purified by MDAP (Method B). The solvent was evaporated in vacuo to give the title compound. LCMS (System B): tRET = 0.63 min; MH+ 238, 240.

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; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; BAXTER, Andrew; BIT, Rino, Antonio; BROWN, John, Alexander; HIRST, David; HUMPHREYS, Philip; JONES, Katherine, Louise; PATEL, Vipulkumar, Kantibhai; (124 pag.)WO2018/41964; (2018); A1;,
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. 934-32-7, name is 1H-Benzo[d]imidazol-2-amine, A new synthetic method of this compound is introduced below., Quality Control of 1H-Benzo[d]imidazol-2-amine

Step 1: 1-Methyl-1H-benzimidazol-2-amine To a solution of 2-aminobenzimidazole (3.0 g, 0.0225 mol) in acetone (30 ml) was added KOH (6.32 g, 0.112 mol) followed by methyl iodide (3.51 g, 0.025 mol) and stirred at room temperature for 10 min. The reaction mixture was diluted with ethyl acetate and the organic layer washed with water, brine and dried over anhydrous Na2SO4 to afford crude residue which was column purified to yield the desired product: 1H NMR (300 MHz, DMSO-d6) delta 3.47 (s, 3H), 6.34 (br s, 2H), 6.82-6.92 (m, 2H), 7.06-7.09 (m, 2H); ESI-MS (m/z) 148.49 (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; Glenmark Pharmaceuticals S.A.; US2009/286811; (2009); 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. 2301-25-9, name is 1-(4-Nitrophenyl)-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., category: imidazoles-derivatives

(2-1) Take 5.07g (27mmol) of intermediate I into a 500mL round bottom flask with magnetons, add 350mL of ethanol, and put it into the collector type constant temperature heating magnetic stirrer, stir and stir to make the intermediate I completely dissolved; (2-2) Further, 0.12 g of palladium carbon was slowly added thereto, and the mixture was thoroughly mixed with the reaction liquid, and then hydrazine hydrate was added in three portions, each time 20.67 mmol (1 mL), a total of 3 mL (62 mmol), and the reaction was carried out for 6 hours, using a thin layer. Chromatographic TLC tracking detection; (2-3) The reaction is terminated, cooled and filtered, and then steamed to 25-30 mL, placed in a fume hood, heated to dryness to 15 mL of a white solid, and dried; (2-4) 40 mL of distilled water was added, and the mixture was stirred at normal temperature for 3 hours to remove hydrazine hydrate, suction filtered, and dried to give 3.88 g of white Intermediate II pure product, yield 91%.

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 2301-25-9.

Reference:
Patent; Fuyang Normal College; Liu Jie; Yang Chao; Zhou Ziyao; Wu Hai; Li Huiquan; (17 pag.)CN109206370; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 714273-83-3,Some common heterocyclic compound, 714273-83-3, name is 5-(tert-Butyl)-1H-imidazole-4-carbaldehyde, molecular formula is C8H12N2O, 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.

General procedure: First diacetyl piperazine diketone (DKP) and the aldehyde intermediate a or deuterium aldehyde compound b condensation reaction to form a heterocyclic compound c or deuterium-containing heterocyclic compound d;

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

Reference:
Patent; Tsingtao Ocean Bio-pharmaceutical Institute Co., Ltd.; Li Wenbao; Ding Zhongpeng; Wang Shixiao; Zhao Jianchun; Guan Huashi; (12 pag.)CN107286139; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem