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. 75370-65-9, name is 4-Amino-1H-benzo[d]imidazol-2(3H)-one, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 4-Amino-1H-benzo[d]imidazol-2(3H)-one

Preparation of 1-(4-(trifluoromethyl)benzyl)-3-(2,3-dihydro-2-oxo-1H-benzo[d]imidazol-4-yl)urea Commercially available 4-trifluoromethylbenzylamine (0.5 ml, 3.5 mmol) was dissolved in 20 ml of AcOEt and at OC triphosgene (1 g, 3.5 mmol) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 5 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (5 ml) of compound 1a (350mg, 2.33mmol) 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 (30ml) and washed with water (1 X 20ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 290mg of a white solid. Yield = 36% 1HNMR (DMSO, 400 MHz) delta 4.40 (2H, d, J = 6 Hz), 6.62 (1H, d, J = 7.2 Hz), 6.84 (2H, m), 6.96 (1H, d, J = 8 Hz), 7.54 (2H, d, J = 8 Hz), 7.70 (2H, d, J = 8.4 Hz), 8.30 (1H, s), 9.99 (1H, bs), 10.60 (1H, bs); [M+1] 351.1 (C16H13F3N4O2 requires 350.3).

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 75370-65-9.

Reference:
Patent; Pharmeste S.r.l.; EP2377850; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 288-32-4, These common heterocyclic compound, 288-32-4, name is 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.

General procedure: Heterocycle (0.1 mol) was added into a solution of EtONa (8.16 g, 0.24 mol) in EtOH (30 mL) heated to reflux. After the solution was stirred for 30 min, 2-chloroethanol (8 g, 0.2 mol) was added dropwise. The resulting suspension was filtered, and the residue was concentrated by vacuum. The crude product was purified by column chromatography on silica gel to yield the desired product. (Rf = 0.3 (EA/ CH3OH= 5:1). The esterification procedure was the same as that in the synthesis of N series.

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

Reference:
Article; Hong, Fengying; Xia, Zhengce; Zhu, Dezhao; Wu, Hongxiang; Liu, Jianhui; Zeng, Zhuo; Tetrahedron; vol. 72; 10; (2016); p. 1285 – 1292;,
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. 7189-69-7, name is 1,1′-Sulfonyldiimidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 1,1′-Sulfonyldiimidazole

General procedure: A solution of 500 mg (4.46 mmol) of 2-fluorophenol 1.769 g (8.92 mmol) of 1,1?-sulfonyldiimidazole in 15 mL of tetrahydrofuran was treated with 727 mg (2.23 mmol) of cesium carbonate. The reaction was stirred for 12 h, concentrated, and the residue was partitioned between the ethyl acetate and water (10 mL each). The organic layer was washed sequentially with saturated ammonium chloride solution and brine. After drying over the anhydrous sodium sulfate, the organic layer was concentrated and chromatographed on silica with 1:5 ethyl acetate / hexane as the eluant to afford 880 mg (90%) of 11bas a clear oil:

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:
Article; Yang, Baocheng; Sun, Zhexun; Liu, Changzhi; Cui, Yan; Guo, Zhilei; Ren, Yuwei; Lu, Zhijian; Knapp, Spencer; Tetrahedron Letters; vol. 55; 49; (2014); p. 6658 – 6661;,
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

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

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

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

Electric Literature 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.

2,6-Dichloro-4-nitro-phenol (243 mg, 1.17 mmol) is dissolved in methylene chloride (2 mL). To the solution is added (3-methyl-2-nitro-3H-imidazol-4-yl)-niethanol (115 mg, 0.732 mmol) and triphenylphosphine (211 mg, 0.805 mmol). The mixture is stirred at roomtemperature until a solution is achieved. The solution is then cooled in an ice bath and treated with diisopropyl azodicarboxylate, DIAD (158 mu,, 0.805 mmol). After 1 hour the ice bath is removed and the mixture is stirred overnight at room temperature. Crude product is purified on a silica gel column to isolate the product mixed with triphenylphosphine oxide. The solids are triturated with t-butyl methyl ether to remove the triphenylphosphine oxide to afford 5-(2,6- dichloro-4-nitro-phenoxymethyl)- 1 -methyl-2-nitro- IH-imidazole. MS (ESI+) for C11H8Cl2N4O5 m/z 347.0 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, its application will become more common.

Reference:
Patent; GENCIA CORPORATION; KHAN, Shaharyar; (80 pag.)WO2018/129258; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 195053-92-0, The chemical industry reduces the impact on the environment during synthesis 195053-92-0, name is 2-(1-Trityl-1H-imidazol-4-yl)ethanamine, I believe this compound will play a more active role in future production and life.

A mixture of Meldrum’s acid (5.52 g, 38.3 mmol), potassium carbonate (26.5 g, 191 mmol) and methyl iodide (7.15 mL, 115 mmol) in acetonitrile (75 mL) was heated at 75 C in a sealed tube for 7 hrs. The mixture was cooled to room temperature, diluted with dichloromethane (300 mL), filtered and the filtrate evaporated to dryness in vacuo. Ethyl acetate (75 mL), hexanes (75 mL) and water (50 mL) were added and phases were separated. The organic layer was washed with 10% aqueous solution of sodium thiosulfate (50 mL) and water (50 mL); dried over anhydrous magnesium sulfate and solvent removed in vacuo to give 2,2,5,5-tetramethyl-[1,3]dioxane-4,6-dione as white solid. Yield: 6.59 g (79%). RF (SiO2, chloroform/ethyl acetate, 98:2): 0.60. 1H NMR spectrum (300 MHz, CDCl3, deltaH): 1.76 (s, 6 H); 1.65 (s, 6 H). A solution of 2-(1-Trityl-1H-imidazol-4-yl)-ethyl amine (5.00 g, 14.2 mmol) prepared as described above and triethylamine (9.86 mL, 70.7 mmol) in toluene (80 mL) was added dropwise over 50 min to a solution of the above dione compound (3.65 g, 21.2 mmol) in toluene (40 mL) at 75 C. The mixture was stirred at this temperature for additional 3 hrs (until the starting amine was detected on TLC), then it was evaporated to dryness. The residue was redissolved in chloroform (300 mL) and washed with 10% aqueous solution of citric acid (200 mL). The aqueous phase was extracted with chloroform (2 x 60 mL); the chloroform phases were combined, dried over anhydrous magnesium sulfate and solvent removed in vacuo. The residue was triturated with hot chloroform (140 mL); hexanes (70 mL) were added and the suspension was stirred at room temperature overnight. Solids were filtered off, washed with chloroform/hexanes mixture (1:1, 2 x 50 mL) and dried in vacuo to give the title product. Yield: 6.73 g (88%). M.p.: 161-162 C. RF (SiO2, chloroform/methanol, 85:15): 0.40. 1H NMR spectrum (300 MHz, DMSO-d6, deltaH): 12.45 (bs, 1 H); 7.66 (t, J=5.1 Hz, 1 H); 7.57-7.31 (m, 9 H); 7.26 (s, 1 H); 7.20-7.02 (m, 6 H); 6.66 (s, 1 H); 3.25 (m, 2 H); 2.57 (t, J=7.3 Hz, 2 H); 1.21 (s, 6 H).

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-(1-Trityl-1H-imidazol-4-yl)ethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Novo Nordisk A/S; SAUERBERG, Per; LAU, Jesper; LINDEROTH, Lars; KODRA, Janos Tibor; SPETZLER, Jane; GARIBAY, Patrick William; (119 pag.)EP3000482; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 172499-76-2, name is Ethyl 3-(1H-imidazol-2-yl)propanoate, 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 172499-76-2, Safety of Ethyl 3-(1H-imidazol-2-yl)propanoate

General procedure: A suspension of tBuOK (1.1 equiv. or 2.2 equiv.) and the imidazole derivative (1.0 equiv.) in DMF (6 mL/mmol) was stirred at rt for 1 h. The reaction mixture was treated with the corresponding alkyl bromide or alkyl mesylate (1.3 equiv. or 2.0 equiv.) and the temperature was raised up to 60 C and stirred at this temperature for 72 h. The solution was then diluted with EtOAc (20 mL/mmol) and washed three times with brine and H2O. The organic layers were dried over MgSO4, filtered, and concentrated. The crude product was purified by CC.

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, Ethyl 3-(1H-imidazol-2-yl)propanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kerscher-Hack, Silke; Renukappa-Gutke, Thejavathi; Hoefner, Georg; Wanner, Klaus T.; European Journal of Medicinal Chemistry; vol. 124; (2016); p. 852 – 880;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem