Category: imidazoles-derivatives

Some common heterocyclic compound, 934-22-5, name is 6-Aminobenzimidazole, molecular formula is C7H7N3, 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. Formula: C7H7N3

To a solution of 2,4-dichloropyrimidine (1 mmol) and 5-Aminobenzimidazole (1 mmol) in 5 ml EtOH, was added Et3N(1 mmol). The reaction mixture was refluxed for 5 hours. After removal of the solvent in vacuo and addition of H2O, the mixture was extracted with EtOAc. The organic layers were combined, washed with a saturated NaCl aqueous solution, dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography to give N-(2-chloropyrimidin-4-yl)-1H-benzo[d]imidazol-5-amine in a yield of 80%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 934-22-5, its application will become more common.

Reference:
Patent; Hutchison MediPharma Enterprises Limeted; US2008/255172; (2008); A1;,
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 872-82-2 as follows. Computed Properties of C5H8N2O

0.283 g (1 mmol) of zinc acetylacetonate was dissolved in 20 mLof methanol. In a separate flask 0.224 g (2 mmol) of 4(5)-(bhydroxyethyl)imidazole was dissolved in 5 mL of methanol. Bothsolutions were mixed and stirred for 60 min. The resulting suspensionwas filtered, the filtrate was concentrated to a small volumeand left to evaporate. After 3 years a small amount of colorlesscrystals was formed in the yellow oil. The compound was characterizedonly by X-ray diffraction.

According to the analysis of related databases, 872-82-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ciborska, Anna; Do??ga, Anna; Kentner, Weronika; Ma?lewski, Piotr; Wyrzykowski, Dariusz; Polyhedron; vol. 178; (2020);,
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 57090-88-7 as follows. Application In Synthesis of 1H-Imidazole-4-carbonitrile

A 22-L, four-neck, round-bottom flask equipped with a mechanical stirrer, a temperature probe, and an addition funnel with a nitrogen inlet was charged with 1H-imidazole-4-carbonitrile (830 g, 8.91 mol, as prepared in the previous step), potassium carbonate (2.47 kg, 17.8 mol), and acetone (6.0 L). Agitation was initiated and the mixture was cooled to 10¡ã C. with an ice bath. SEMCl (1.50 kg, 9.00 mol) was added through the addition funnel over 210 min to maintain the internal temperature below 15¡ã C. The reaction was then allowed to warm to ambient temperature and stirred at ambient temperature overnight (20 h). The reaction mixture was then cooled in an ice bath to 10¡ã C. and quenched by the slow addition of water (8.0 L) over 30 min to maintain the internal temperature below 30¡ã C. The resulting mixture was transferred to a 22-L separatory funnel and extracted with ethyl acetate (2.x.7.0 L). The combined organics were concentrated under reduced pressure at 35¡ã C. to give the crude product as a dark brown oil, which was purified through a plug of silica gel (16.5.x.20 cm, 2.4 kg silica gel) using 2:1 heptane/ethyl acetate (15 L) as eluent. The fractions containing the product were combined and concentrated under reduced pressure at 35¡ã C. to afford a mixture of the title compounds as a light brown oil [1785 g, 90percent). The 1H NMR spectrum was consistent with the assigned structure and indicated the presence of a 64:36 ratio of regioisomers.

According to the analysis of related databases, 57090-88-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Baumann, Christian Andrew; Gaul, Michael David; Johnson, Dana L.; Tuman, Robert W.; US2006/281788; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 17334-08-6, A common heterocyclic compound, 17334-08-6, name is (1-Methyl-1H-imidazol-2-yl)methanol, molecular formula is C5H8N2O, 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.

This compound was synthesised using a modified procedure described in literature.6 1-Methyl-2-hydroxymethyl imidazole (6.500 g, 58.000 mmol) was added in small portions to SOCl2 (12.7 mL, 174 mol) at 0 C. The mixture was heated under reflux for 30 min. After cooling, the solution was concentrated under reduced pressure followed by recrystallization from ethanol (17 mL) to afford 2-(chloromethy1)-1-methyl-1H-imidazole hydrochloride. Yellow crystals; 7.580g, yield: 78%. The NMR spectrum was according to literature.6 1H NMR (CDCl3) delta = 7.79 (d, 1H, J = 1.9 Hz; ImH), 7.70 (d, 1H, J = 1.9 Hz; ImH), 5.20 (s, 2H; CH2Cl), 3.86 ppm (s, 3H; NCH3).

The synthetic route of 17334-08-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ionescu, Alexandra; Cornut, Damien; Soriano, Sebastien; Guissart, Celine; Van Antwerpen, Pierre; Jabin, Ivan; Tetrahedron Letters; vol. 54; 45; (2013); p. 6087 – 6089;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 934-22-5,Some common heterocyclic compound, 934-22-5, name is 6-Aminobenzimidazole, molecular formula is C7H7N3, 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.

The respective 2-oxo benzoic acid (1 eq.) was dissolved in THF (5 ml in case of 1 mmol) and DCC (1 eq.) was added. After stirring at r.t. for 1 h, benzimidazol-5(6)-amine (1 eq.) was added and stirring at r.t. was continued for 24 h. The mixture was put into the fridge for 2 h and afterwards the precipitated solid was filtered off. The filtrate was concentrated in vacuo, re-dissolved in a mixture of AcOH and toluol (3 ml and 7 ml in case of 1 mmol batch) and refluxed over night. After cooling the solvents were evaporated. The resulting residue was dissolved in CH2Cl2 (10 ml in case of 1 mmol batch), cooled to 0 C. and treated with TFA (1 ml (4 ml) per mmol). After stirring at r.t. for 10 min, triethylsilane (2 eq. (4 eq.)) was added. The reaction was allowed to warm up to room temperature and stirred for 3 h. After that time, the mixture was quenched with saturated sodium bicarbonate solution. The organic layer was separated and the aqueous layer was extracted with EtOAc (3¡Á25 ml). The combined organic layers were dried over Na2SO4, concentrated in vacuo and the remaining residue was purified by flash-chromatography using silica gel and a CHCl3/MeOH gradient. Example 1262-(1H-benzo[d]imidazol-5-yl)-3-(4-biphenyl)isoindolin-1-oneThe compound was synthesized according to method 11.2-(4-Phenylbenzoyl)benzoic acid (1.0 g; 3.3 mmol), DCC (680 mg; 3.3 mmol), benzimidazol-5(6)-amine (440 mg; 3.3 mmol), TFA (3.92 ml) and triethylsilane (0.624 ml; 3.92 mmol; 4 eq.) and was additional purified by semi-preparative HPLC; yield: 0.120 g (9.1%); MS m/z: 402.1 [M+H]+; 1H-NMR (DMSO d6, 400 MHz): delta 6.79 (s, 1H); 7.28-7.32 (m, 1H); 7.36-7.40 (m, 5H); 7.53-7.60 (m, 5H); 7.63-7.66 (m, 1H); 7.72-7.74 (d, 1H, 3J=8.7 Hz); 7.76-7.79 (dd, 1H, 4J=1.7 Hz, 3J=8.7 Hz); 7.89-7.91 (m, 1H); 8.17-8.18 (d, 1H, 4J=1.7 Hz); 9.06 (s, 1H); HPLC (Gradient 3): rt 15.20 min (97.0%)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Aminobenzimidazole, its application will become more common.

Reference:
Patent; PROBIODRUG AG; US2011/92501; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

17334-08-6, name is (1-Methyl-1H-imidazol-2-yl)methanol, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Safety of (1-Methyl-1H-imidazol-2-yl)methanol

2-Chloromethyl-1-methyl-imidazolhydrochloride The 2-chloromethyl-1-methyl-imidazolhydrochloride is produced according to the description above. 20 ml thionylchloride is added to a suspension of 5.61 g 1-methylimidazolyl-1-methanol in 5 ml dry benzene. Two phases are built. Stir vigorously for half an hour. Then the combined solvents are rotated off and a bright brown product remains. 1H-NMR (CDCl3; 270 MHz): 7.75 (d; 1H); 7.68 (d; 1H); 5.16 (s; 2H); 3.86 (s, 3H); 3.42 (s; 3H). 13C-NMR: 141.5; 124.7; 119.4; 34.2; 31.7 ppm.

The synthetic route of 17334-08-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Unilever Home & Personal Care USA, division of Conopco, Inc.; US6646122; (2003); 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. 2403-66-9, name is 3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: imidazoles-derivatives

In a 300 ml recovery flask, 17.62 g (100.0 mmol) of 2- (3-hydroxypropyl) benzimidazole,22.26 g (220.0 mmol) of triethylamine, 0.22 g (1.0 mmol) of 3,5-di-tert-butyl-4-hydroxytoluene and 200 ml of tetrahydrofuran were added to prepare a reaction solution. After the reaction solution was cooled to 0 C., 23.00 g (220.0 mmol) of methacryloyl chloride was added dropwise and the mixture was stirred at room temperature for 3 hours, and the precipitated triethylamine hydrochloride was filtered off.Then, the filtrate was concentrated and 200 ml of methanol and 0.54 g (10.0 mmol) of sodium methoxide were added to the solution to prepare a solution, and the mixture was stirred at room temperature for 1 hour. Subsequently, this solution was concentrated and extraction operation with 100 ml of ethyl acetate was carried out three times, and the extracted solutions were mixed and concentrated to obtain a dry matter. This dry matter was dissolved in ethyl acetate 10 mlAnd 10 ml of hexane to obtain 14.48g (yield: 59%) of white crystals.

The synthetic route of 2403-66-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SHIKOKU CHEMICALS CORPORATION; OKUMURA, NAOTO; IKEDA, YUICHI; (27 pag.)JP2015/20962; (2015); 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 1003-21-0 as follows. Recommanded Product: 1003-21-0

To a 3 L 4-neck flask equipped with an overhead stirrer, nitrogen bubbler, and thermocouple was added 5-bromo-1-methyl-1H-imidazole (47.96 g, 297.9 mmol), followed by THF (537 mL). To this room temperature solution was added isopropylmagnesium chloride/lithium chloride complex [1.3 M] (246.8 mL, 320.8 mmol) (addition temperature maintained between 16.6 and 25 C.) to afford a milky suspension and the reaction was stirred for 60 minutes and then cooled to 5.3 C. in an ice bath. To this mixture was added a solution of N-methoxy-N-methyl-6-(trifluoromethyl)nicotinamide (53.66 g, 229.14 mmol, Intermediate 15, step b) in THF (268.3 mL) (addition temperature between 5.3 and 5.6 C.) to afford an orange mixture. After addition, the reaction was warmed to room temperature over 2 hours. After stirring at room temperature for 18 hours, THF (200 mL) was added and the reaction was stirred for 2 hours. The reaction was then cooled to 4 C. with an ice bath and carefully quenched with 2N HCl to a pH=7, quenching temperature reached 12 C. The mixture was diluted with ethyl acetate (500 mL), phase split and the organic layer was washed with brine (2¡Á200 mL) and dried over sodium sulfate, filtered, and the solvent was removed. Hot ether was added and then filtered to give the title compound as a solid

According to the analysis of related databases, 1003-21-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Janssen Pharmaceutica NV; Leonard, Kristi A.; Barbay, Kent; Edwards, James P.; Kreutter, Kevin D.; Kummer, David A.; Maharoof, Umar; Nishimura, Rachel; Urbanski, Maud; Venkatesan, Hariharan; Wang, Aihua; Wolin, Ronald L.; Woods, Craig R.; Fourie, Anne; Xue, Xiaohua; Mirzadegan, Taraneh; Ganamet, Kelly; US2014/107097; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 934-32-7, 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. 934-32-7, name is 1H-Benzo[d]imidazol-2-amine, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of ethyl acetoacetate and/or acetylacetone (1 mmol) or malononitrile(1.1 mmol), 2-aminobenzimidazole (1 mmol), aldehyde (1 mmol) and [PVPH]ClO (30 mg, 6.84 mol %) was heated at 100 C in an oil bath for the appropriate time.After completion of the reaction [monitored by thin layer chromatography (TLC): nhexane:ethyl acetate (3:1)], the reaction mixture was cooled to room temperatureand EtOH (5 mL) was added to it and filtered to separate the catalyst. Afterevaporation of the solvent from the filtrate, the crude solid product wasrecrystallized from ethanol to obtain pure A or B products.The spectral [IR, proton ( 1H) NMR and 13C NMR] data of new compounds arepresented below.

The chemical industry reduces the impact on the environment during synthesis 1H-Benzo[d]imidazol-2-amine. I believe this compound will play a more active role in future production and life.

Reference:
Article; Abedini, Masoumeh; Shirini, Farhad; Mousapour, Maryam; Goli Jolodar, Omid; Research on Chemical Intermediates; vol. 42; 7; (2016); p. 6221 – 6229;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 1546-79-8, These common heterocyclic compound, 1546-79-8, name is 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone, 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.

Ethylmagnesium bromide (3M in ethyl ether, 3.95 ml, 11.84 mmol) is added dropwise to example 21a (1.6 g, 5.92 mmol) dissolved in anhydrous THF (20 mL) cooled to 0 C. Stirring is continued at 0 C. for 15 min then overnight at room temperature. The reaction mixture is cooled to 0 C. and methylmagnesium bromide (3M in ethyl ether, 1.97 ml, 5.92 mmol) is added dropwise. Stirring is continued at 0 C. for 15 min followed by 2 h at room temperature. The reaction mixture is cooled to 0 C., aqueous NH4Cl is added dropwise and stirring is continued for 5 min EtOAc is added, the organic layer separated, washed with brine, dried over Na2SO4 and concentrated under reduced pressure to furnish 1.37 g of crude ketone. Lithium bis(trimethylsilyl)amide (1.8M, 1.03 mL, 1.86 mmol) is added dropwise to the crude ketone (370 mg, 1.55 mmol) dissolved in anhydrous THF (10 mL) and cooled to -78 C. Stirring is continued at -20 C. for 1 h. The reaction mixture is cooled to -78 C. and 1-(trifluoroacetyl)imidazole (0.70 ml, 6.18 mmol) is added. Stirring is continued 3 h at room temperature. Aqueous NH4Cl solution and EtOAc are added, the organic layer is separated, dried over a phase-separator cartridge and concentrated under reduced pressure to furnish a residue that is purified by Si flash chromatography (5-40% EtOAc/Hexane as eluent) to obatain 190 mg of intermediate. Hydroxylamine hydrochloride (512 mg, 7.37 mmol) is added to such product dissolved in MeOH (20 mL) and the reaction mixture refluxed for 2 h. Volatiles are evaporated under reduced pressure, the residue is partitioned between EtOAc and saturated NaHCO3, the organic layer is separated, washed with saturated NaHCO3, dried over phase separator cartridge and concentrated under reduced pressure to furnish a 90 mg of residue. TEA (50 muL, 0.36 mmol) followed by methanesulfonyl chloride (26 muL, 0.33 mmol) are added to such residue dissolved in DCM (10 mL) and cooled to 0 C. Stirring is continued at room temperature then further TEA (50 muL, 0.36 mmol) and methanesulfonyl chloride (26 muL, 0.33 mmol) are added and stiffing is continued for 2 h. Water and DCM are added, the aqueous layer is further extracted with DCM, the organic layers are combined, dried over a phase-separator cartridge and concentrated under reduced pressure. The resulting residue is purified by flash chromatography (eluent 0-10% EtOAc/hexane) to furnish the title compound (20 mg, 23% on the last step).

The synthetic route of 1546-79-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GIOVANNINI, Riccardo; BERTANI, Barbara; FERRARA, Marco; LINGARD, Iain; MAZZAFERRO, Rocco; ROSENBROCK, Holger; US2013/197011; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem