Month: March 2021

Some common heterocyclic compound, 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, molecular formula is C5H6N2O2, 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. category: imidazoles-derivatives

d) 3-(3,3-Difluoro-2,2-dimethyl-indan-1-yl)-3H-imidazole-4-carboxylic acid methyl ester; To a solution of 3,3-difluoro-2,2-dimethyl-indan-1-ol (388 mg, 1.96 mmol) in THF (16 ml.) is added methyl 4-imidazolecarboxylate (CASNo. 17325-26-7, 370 mg, 2.94 mmol), and triphenylphosphine (770 mg, 2.94 mmol). The reaction is cooled to 0 0C and di-f-butyl azodicarboxylate (670 mg, 2.94 mmol) is added. The reaction is placed at room temperature and permitted to stir for six hours and then is heated to 40 0C overnight. The next day the reaction mixture is cooled to 0 0C and quenched with 4 N HCI in dioxane (5 ml_, 20 mmol) and stirred for 30 minutes. The reaction is concentrated to near dryness and diluted with ethyl acetate. The organic layer is extracted three times with 1 N aqueous HCI. The aqueous extracts are combined, neutralized with Na2CO3, and extracted three times with ethyl acetate. The combined organic layers are dried with Na2SO4, filtered, and concentrated. The resulting residue is purified by silica gel flash chromatography (ethyl acetate-dichloromethane, 0:1 to 1:5) to furnish 3-(3,3-difluoro-2,2-dimethyl-indan-1-yl)-3H- imidazole-4-carboxylic acid methyl ester. MS: (ESI) m/z 307.0 (M+H)+; 1H NMR (400 MHz, CDCI3) delta ppm 0.87 (d, J=2.5 Hz, 3 H), 1.33 (d, J=3.0 Hz, 3 H)1 3.96 (s, 3 H), 6.43 (d, J=2.8 Hz, 1 H), 7.17 (s, 1 H), 7.30 – 7.37 (m, 1 H), 7.56 – 7.64 (m, 2 H), 7.69 – 7.76 (m, 1 H), 7.85 (s, 1 H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 17325-26-7, its application will become more common.

Reference:
Patent; NOVARTIS AG; WO2008/76336; (2008); A2;,
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. 71759-87-0, name is 4-Iodo-1-methyl-1H-imidazole, A new synthetic method of this compound is introduced below., Quality Control of 4-Iodo-1-methyl-1H-imidazole

To a solution of 4-iodo-l -methyl- l/f-imidazole (0.31 g, 1.50 mmol) in dichloromethane (5 mL) was added ethylmagnesium bromide (3.0 M solution in tetrahydrofuran, 0.50 mL, 1.50 mmol). The reaction mixture was stirred at room temperature for 15 minutes and a solution of 3,5-dichloro-6-(2,6-difluorophenyl)-l-(2- methylpropyl)-2(lH)-pyrazinbne (i.e. the product of Example 10 step A) (0.50 g, 1.50 mmol) in dichloromethane (5 mL) was added. The reaction mixture was stirred at room temperature overnight, and then quenched with saturated aqueous ammonium chloride solution (1 mL). The resulting mixture was passed through ChemElute, diatomaceous earth column by Varian, and concentrated under reduced pressure to give an oil. This residue EPO was purified by silica gel flash chromatography (5 % methanol in ethyl acetate as eluant) to afford 150 mg of the title product, a compound of the present invention. 1H NMR (CDCl3) delta 8.35 (s, IH), 7.59 (s, IH)5 7.58-7.51 (m, IH), 7.08 (t, 2H)5 3.78-3.74 (m, 5H), 2.01-1.92 (m, IH), 0.76 (d, 6H).

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; E.I. DUPONT DE NEMOURS AND COMPANY; WO2006/89060; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 3314-30-5,Some common heterocyclic compound, 3314-30-5, name is 1H-Benzo[d]imidazole-2-carbaldehyde, molecular formula is C8H6N2O, 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.

0.21 g (0.54 mmol) of compound L4 was dissolved in 3 mL of ethanol, Under stirring, 0.10 g (0.65 mmol, 1.2 eq) of compound L6 was added, Dropping 2 drops of piperidine, Oil bath reflux 45min, TLC detection reaction is complete. The solvent was distilled off, Get red oil, Column chromatography separation, Dichloromethane-methanol gradient elution, Take the main product, So that it is completely completely dissolved in ethanol, A solution of HCl-ether was added dropwise to a pH of 2, Standing, There is a red solid precipitation. Filter, The filter cake was washed with a large amount of anhydrous ether to neutral, The resulting red solid was recrystallized from ethanol to give 9.8 mg.

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

Reference:
Patent; Institute of Radiation Medicine, Academy of Military Medical Sciences; Wang, Lin; Wang, Jieying; Yan, Haiyan; Zhang, Shouguo; Peng, Tao; Wen, Xiaoxue; Wang, Gang; Ding, Rui; Li, Lu; (24 pag.)CN104211632; (2016); B;,
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. 104619-51-4, name is Di(1H-imidazol-1-yl)methanimine, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 104619-51-4

To 5-hydrazino-3-phenyl-2-(4-{ [4-(5-pyridin-2-yl-lH-l,2,4-triazol-3-yl)piperidm-l- yl]methyl}phenyl)-l,6-naphthyridine (1-3) (70 mg, 0.126 mmol) in DMF (1.5 mL) was added literature known 1,1-di-lH-imidazol-l-ylmethanimine (102 mg, 0.633 mmol). The reaction mixture was stirred at 85C for 4 hours, concentrated in vacuo, and chromatographed to furnish the desired 9-phenyl-8-(4- { [40(5-pyridin-2-yl-lH-l,2,4-triazol-3-yl)piperidin-l-yl]emthyl}phenyl}[l,2,4]triazolo[3,4-f]-l,6- naphthyridin-3-amine (1-4) (46 mg) as its trifluoroacetic acid salt. 1H NMR: (500MHz, CDCl3) delta 8.76 (s, IH), 8.74 (d, J= 4.3 Hz, IH), 8.29-8.27 (m, 2 H), 8.19 (m, IH), 7.67 (m, IH), 7.54-7.53 (m, 2H), 7.48- 7.46 (m, 2H), 7.47 (d, J= 7.7 Hz , IH), 7.34-7.26 (m, 5H), 4.43 (s, 2H), 3.65 (br d, J= 10.9 Hz, 2H), 3.46 (br s, 1 H), 3.27-3.19 (m, 2H), 2.50-2.42 (m, 2H), 2.10-2.06 (m, 2H).

According to the analysis of related databases, 104619-51-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2006/135627; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 760212-58-6, A common heterocyclic compound, 760212-58-6, name is 1-(4-Bromophenyl)-2-phenyl-1H-benzo[d]imidazole, molecular formula is C19H13BrN2, 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.

In an argon atmosphere, 10 g (29 mmol) of 1-(4-bromophenyl)-phenyl-1H-benzimidazole were dissolved into 100 mL of dehydrated THF, and the temperature of the solution was cooled to -78 C. Then, 20 mL of n-butyllithium (in hexane, 1.6 mol/L) were dropped. After the mixture had been stirred at -78 C for 1 hour, the temperature of the mixture was increased to 0C. The temperature of the mixture was cooled to -78 C again, and 9.7 mL (87 mmol) of trimethoxyborane were dropped. The mixture was stirred at -78 C for 1 hour, and was then stirred at room temperature for 2 hours. 100 mL of 10-mass% hydrochloric acid were added, and the whole was stirred for 1 hour, followed by filtration. The organic layer of the filtrate was washed with a saturated sodium chloride solution and dried with magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by means of silica gel column chromatography to obtain 4.2 g of 4-(2-phenyl-1H-benzimidazol-1-yl)phenylboronic acid (46% yield).

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; IDEMITSU KOSAN CO., LTD.; EP1734038; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 3034-50-2, These common heterocyclic compound, 3034-50-2, name is Imidazole-4-carbaldehyde, 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 mixture of 3C (4.35 g, 21.16 mmol) in anhydrous dichloroethane (60 mL) was treated with imidazole-4-carboxaldehye (1B, 2.79 g, 28.99 mmol) and AcOH (0.35 mL, 6 mmol). The mixture was stirred at RT for 10 min and then treated with NaBH(OAc)3 (15.36 g, 72.48 mmol). The reaction mixture was stirred at RT overnight, and quenched with 2N NaOH solution, concentrated under vacuum. The residue was diluted with water (50 mL) and extracted with EtOAc (4¡Á100 mL). The organic layer was dried (MgSO4), filtered, and concentrated under vacuum. Chromatography (DCM containing 1 to 5% of 7N NH3 in MeOH) provided 3D (5.56 g, 89%). MS m/z 261 (MH+).

The synthetic route of 3034-50-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Schering Corporation and Pharmacopeia Drug Discovery, Inc.; US2007/93477; (2007); 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. 10597-52-1, name is 7-Nitro-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., Application In Synthesis of 7-Nitro-1H-benzo[d]imidazole

A 500-mL round-bottomed flask equipped with a magnetic stirrer and nitrogen inlet is charged with compound 3b (3.30 g, 30.6 mmol), potassium carbonate (8.95 g, 64.8 mmol), anhydrous DMF (200 mL) and 4-chloromethylpyridine hydrochloride (3.98 g, 24.3 mmol) and the mixture is then stirred under nitrogen for 24 h at ambient temperature. After such time the reaction is partitioned between water (200 mL) and ethyl acetate (200 mL). The aqueous layer is separated and extracted with ethyl acetate (6¡Á250 mL). The combined organic extracts are dried with sodium sulfate, and the drying agent is filtered off. The filtrate is then concentrated under vacuum to give a brown solid, which is purified by column chromatography to afford compound 3c as a yellow solid.

The synthetic route of 10597-52-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mitchell, Scott A.; Danca, Mihaela Diana; Blomgren, Peter A.; Brittelli, David R.; Zhichkin, Pavel; Voss, Matthew E.; US2006/270702; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 939-70-8, The chemical industry reduces the impact on the environment during synthesis 939-70-8, name is 1-(1H-Benzo[d]imidazol-2-yl)ethanone, I believe this compound will play a more active role in future production and life.

General procedure: A 10%solution of NaOH (5 ml) in EtOH was added to a solutionof 2-acetylbenzimidazole (4) (1.6 g, 0.01 mol) in absoluteEtOH (20 ml) at 0C with stirring. Then the solution of anaromatic aldehyde (0.01 mol) in absolute EtOH (10 ml)was added dropwise. The reaction mixture was stirred for12 h at room temperature. After completion of reaction(monitored by TLC), the reaction mixture was poured ontocrushed ice. The separated solid was filtered off, washedwith water, and dried. The residue was purified by columnchromatography (silica gel, eluent 10% ethyl acetate inpetroleum ether) to afford pure benzimidazole-derived chalcone 5a-m.

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

Reference:
Article; Meshram, Gangadhar A.; Vala, Vipul A.; Chemistry of Heterocyclic Compounds; vol. 51; 1; (2015); p. 44 – 50; Khim. Geterotsikl. Soedin.; vol. 51; 1; (2015); p. 44 – 50,7;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 85330-50-3, name is 4-Nitro-1H-benzo[d]imidazol-2(3H)-one, 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 85330-50-3, HPLC of Formula: C7H5N3O3

Preparation of 4-amino-1H-benzo[d]imidazol-2(3H)-one 1a (scheme 2) To compound 4a (2g, 11.6mmol) dissolved in a mixture of 4/1 MeOH/THF (100ml) was added C/Pd 10% (500mg) and the reaction was hydrogenated at 60 psi overnight. (TLC AcOEt 9 / MeOH 1) The reaction was filtrated through a pad of Celite and the filtrate was evaporated under vacuum. The crude solid was crystallized from ether giving 1,5g of a white solid. Yield = 88%. 1HNMR (DMSO, 200 MHz) delta 4.84 (2H, bs), 6.22 (2H, m), 6.65 (1H, t, J = 8 Hz), 9.98 (1H, bs), 10.33 (1H, bs)

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

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

Related Products of 45676-04-8,Some common heterocyclic compound, 45676-04-8, name is 1-tert-Butylimidazole, molecular formula is C7H12N2, 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.

E) 1,1′-Di-tert-butyl-3,3′-methylenedimidazolium dibromide 12 0.008 mol of dibromomethane (1.391 g; 0.56 ml) and 5 ml of tetrahydrofuran are added to 0.016 mol of tertbutylimidazole 2 (2.000 g) in an ACE pressure tube. The reaction mixture is stirred at 80 C. for 20 hours. The solid which precipitates is washed repeatedly with a little tetrahydrofuran. A white solid 12 is obtained. Empirical formula: C15H26N4Br2 M=422.206 g/mol Yield: 1.449 g (42.9% of theory) Melting point: decomposition at >230 C. 1H (ppm, d6-DMSO, 300.13 MHz): delta=9.85 (s, 2H, NCN); 8.21 (s, 2H, NCCHN); 8.17 (s, 2H, NCHCN); 6.67 (s, 2H, NC2N); 1.62 (s, 18H, C3 group)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-tert-Butylimidazole, its application will become more common.

Reference:
Patent; BASF SE; TECHNISCHE UNIVERSITAET DRESDEN; US2009/326237; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem