Tag: M.W=100-200

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

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

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

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

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

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

Some common heterocyclic compound, 137049-00-4, name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, molecular formula is C4H5ClN2O2S, 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. Recommanded Product: 1-Methyl-1H-imidazole-4-sulfonyl chloride

2.2 Ethyl 1-(3,4-dichlorobenzyl)-7-(2-(1-methyl-1 H-imidazole-4-sulfonamido)ethoxy)- 1 ,2,3,4-tetrahydronaphthalen-2-ylcarbamate; Ethyl 7-(2-aminoethoxy)-1 -(3,4-dichlorobenzyl)-1 ,2,3,4-tetrahydronaphthalen-2- ylcarbamate hydrochloride (100 mg, 0.229 mmol) and DMAP (27.9 mg, 0.229 mmol) were dissolved in CH2CI2 (15 ml) and 1-methyl-1 H-imidazole-4-sulfonyl chloride (41.3 mg, 0.229 mmol) dissolved in CH2CI2 (15 ml) was added. The reaction mixture was stirred over night at RT. After addition of H2O the phases were separated and the aqueous phase was extracted with CH2CI2. The organic layer was washed with HCI (1 N), NaHCO3 solution and NaCI solution, then dried on MgSO4 and the solvent was removed. To the residue EtOAc/ diethylether (1 :1 ) was added, stirred, and the precipitate was separated by filtration to obtain a brown solid of product (100 mg). ESI-MS [M+H+] = 581.5 Calculated for C26H30CI2N4O5S = 580.13

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 137049-00-4, its application will become more common.

Reference:
Patent; ABBOTT GMBH &; CO. KG; AMBERG, Wilhelm; OCHSE, Michael; LANGE, Udo; KLING, Andreas; BEHL, Berthold; HORNBERGER, Wilfried; MEZLER, Mario; HUTCHINS, Charles; WO2010/92180; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1615-14-1,Some common heterocyclic compound, 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol, molecular formula is C5H8N2O, 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.

Diethyl azodicarboxylate (435 mg, 2.5 mmol) was added dropwise to a suspension of 7-hydroxy-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin4-one (612 mg, 2 mmol), 2-(imidazol-1-yl)ethanol (280 mg, 2.5 mmol), (J. Med. Chem. 1993, 25 4052-4060), and triphenylphosphine (655 mg, 2.5 mmol) in methylene chloride (10 ml) at 5 C. The mixture was stirred for 10 minutes at 5 C. and then 1 hour at ambient temperature. The mixture was poured directly on to a silica column and eluted with methylene chloride/methanol (95/5) to give 7-(2-(imidazol-1-yl)ethoxy)-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (640 mg, 80%). 1H NMR Spectrum: (CDCl3) 1.19(s, 9H); 3.98(s, 3H); 4.34(m, 2H); 4.45(m, 2H); 5.94(s, 1H); 7.02(s, 1H); 7.07(s, 1H); 7.11(s, 1H); 7.64(s, 1H); 7.67(s, 1H); 8.17(s, 1H). MS-ESI: 423 [MNa]+

The synthetic route of 1615-14-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zeneca Limited; US6265411; (2001); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 38993-84-9,Some common heterocyclic compound, 38993-84-9, name is (1-Methyl-1H-imidazol-5-yl)methanol, molecular formula is C5H8N2O, 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.

Thionyl chloride (3.88mL, 53.5mmol) was added dropwise to 3-methyl-3H-imidazol-4- yl)-methanol (o.3g, 2.68mmol). The reaction was sonicated briefly, treated with DMF (1 drop) and allowed to stir at ambident temperature for 1 h. The volatiles were removed and the residue treated with diethyl ether. The diethyl ether was decanted and the procedure repeated 3 times. The semi-solid residue was treated with dimethylamine in THF (6.69mL, 13.38mmol) followed DMF (1 mL). The reaction was heated in a CEM microwave reactor at 8O0C for 30 minutes, treated with acetic acid (1 ml_) and purified by SCX cartridge to give the title compound (0.18g, 1.22mmol). LC-MS (method 1): R, 2.9 min, m/z 140 [MH]+.

The synthetic route of 38993-84-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARGENTA DISCOVERY LIMITED; ASTRAZENECA AB; WO2008/23157; (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 85330-50-3 as follows. Application In Synthesis of 4-Nitro-1H-benzo[d]imidazol-2(3H)-one

b)Preparation of 4-amino-benzimidazolin-2-one To a solution of 4-nitro-benzimidazolin-2-one (700 mg, 3.9mmol) in methanol(50 ml) and acetic acid (10 ml) was added 10% Pd/C (200 mg). The mixture was flushed with argon, then hydrogen was bubbled through the solution for 10 ain. and a hydrogen atmosphere was maintained at balloon pressure overnight. The mixture was filtered through celite and the celite was washed with methanol. The solvent was evaporated and chromatography of the resulting solid on silica gel (10%MeOH/CH2C2) gave the desired product (500 mg, 86%). 1H NMR (CD3SO2CD3): delta10.34 (s, 1H), 10.01 (s, 1H), 6.66 (t, 1H), 6.24 (d,1H), 6.22 (d, 1H), 5.15 (bs, 2H).

According to the analysis of related databases, 85330-50-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SmithKline Beecham Corporation; US6300325; (2001); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem