Tag: M.W=100-200

Electric Literature of 15965-31-8, 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. 15965-31-8, name is 5-Chloro-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows.

A solution of 2-chloro-l-[2-chloro-4-(4-chlorophenoxy)phenyl]ethanone (550 mg; 1.74 mmol) and 4- chloroimidazole (214 mg; 2.09 mmol; 1.20 eq) in dry acetonitrile (5.0 mL) was stirred at 80C for 20 h, then at 130C for 1 h under microwave irradiation. Thereafter the reaction mixture was allowed to cool down to room temperature, diluted with water, the organic layer was washed with saturated aqueous sodium bicarbonate, dried (MgSO i) and concentrated to dryness in vacuo. The oily residue was purified by chromatography over silica gel, eluted with a mixture of w-heptane/ethyl acetate (100:0 to 0: 100). After evaporation of the solvents, a second purification by preparative HPLC was performed. Evaporation of the solvents in vacuo afforded 141 mg (21%) of l-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-(5-chloroimidazol- l-yl)ethanone as a colourless solid. MS (ESI): 381.0 ([M+H]+)

The chemical industry reduces the impact on the environment during synthesis 5-Chloro-1H-imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; BAYER AKTIENGESELLSCHAFT; COQUERON, Pierre-Yves; BERNIER, David; GENIX, Pierre; MILLER, Ricarda; NAUD, Sebastien; WITTROCK, Sven; BRUNET, Stephane; KENNEL, Philippe; MEISSNER, Ruth; WACHENDORFF-NEUMANN, Ulrike; GOeRTZ, Andreas; (104 pag.)WO2018/60088; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1546-79-8,Some common heterocyclic compound, 1546-79-8, name is 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone, molecular formula is C5H3F3N2O, 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.

5-(5-(4-Bromo-3-fluorophenyl)-4-ethyl-3-trifluoromethyl-1H-pyrazol-1-yl)-2-pyridinesulfonamide (Step 4) To a stirred solution of hexamethyldisilazane (2.5 ml, 11.75 mmol) in tetrahydrofuran (25 ml) was added n-butyllithium (7.5 ml, 11.75 mmol) dropwise at 0 C. under nitrogen. The reaction mixture was stirred at room temperature for 30 min. Then cooled to -78 C., to the mixture was added a solution of 1-(4-bromo-3-fluorophenyl)-1-butanone (2.4 g, 9.79 mmol) in tetrahydrofuran (12 ml) dropwise and stirred at rt for 1 h. Then 1-trifluoroacetylimidazole (1.3 ml, 11.75 mmol) was added to the mixture at same temperature, the mixture was stirred at rt for 5 h. This was quenched by water and the pH was adjusted to pH 4-5, extracted with ethyl acetate. The extracts was dried (MgSO4) and concentrated. This was purified on silica gel eluding with ethyl acetate/hexane (1:20/1:15) to afford 2.7 g (80.9%) as a yellow oil. A mixture of 1-(4-bromo-3-fluorophenyl)-2-ethyl-4,4,4-trifluoro-1,3-butanedione (1.5 g, 4.40 mmol) and 5-hydrazino-2-pyridinesulfonamide hydrochloride (1.28 g, 5.72 mmol) in ethanol (60 ml) was stirred at reflux for 3 h. After cooling, the solvent was removed and the residue was diluted with ethyl acetate, washed with water. The extracts was dried (MgSO4), and concentrated. This was purified on silica gel eluding with ethyl acetate/hexane (1:10/1:5/1:4) to afford 1.64 g (75.6%) of the titled compound as a white amorphous. 1H-NMR (CDCl3) delta: 8.58-8.57 (1H, m), 7.99-7.95 (1H, m), 7.79 (1H, dd, J=8.6, 2.5 Hz), 7.70-7.64 (1H, m), 7.05 (1H, dd, J=8.6, 1.8 Hz), 6.91-6.88 (1H, m), 5.40 (2H, br.s), 2.56 (2H, q, J=7.6H), 1.14 (3H, t, J=7.6 Hz)

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

Reference:
Patent; PFIZER INC.; US2003/144280; (2003); 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. 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., name: 2-Chloro-1H-benzo[d]imidazole

2-Chloro-1H-benzimidazole (7.5 g, 49 mmol) was dissolved in dimethylformamide (20 mL),and the reaction mixture was cooled to oo C. Sodium hydride ( 60% dispersion in mineral oil 2.16 g,5 5.4 mmol) was carefully added. The reaction mixture was stirred at ambient temperature for 1 hour,and after that iodomethane (8.37g, 59 mmol) was added. The reaction mixture was stirred at ambienttemperature overnight, and then water (200 mL) was added. The solid was collected by filtration toafford 5 g, 61% of the titled compound as a white solid. 1H NMR (300 MHz, DMSO-d6) o ppm 3.79(s, 3H), 7.21-7.33 (m, 2H), 7.58 (t, J=7.0 Hz, 2H).

The synthetic route of 4857-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBVIE INC.; GOMTSIAN, Artour; DEKHTYAR, Tatyana; FRANK, Kristine E.; FRIEDMAN, Michael M.; JOSEPHSOHN, Nathan; MOLLA, M-Akhteruzz; VASUDEVAN, Anil; NG, Teresa; SHAFEEV, Mikhail; WO2014/5129; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 2302-25-2, name is 4-Bromo-1H-imidazole, 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 2302-25-2, name: 4-Bromo-1H-imidazole

General procedure: Amberlyst A21 (20 wt %) was added to a mixture of amine (1 mmole) and (Boc)2O (1 mmole) and the mixture was stirred for the appropriate reaction time as specified in (Table 1). The progress of reaction was monitored by Thin layer chromatography (10-20% ethyl acetate: hexane) on TLC plates (Merck) precoated with silica. After completion of reaction, the reaction mass was diluted with methanol, filtered off the catalyst which was washed for several times and then dried at 800 C under reduced pressure for 1 hour and subjected to further recycle study (Table 4). It showed no much more decrease in the product yield indicating high activity of the catalyst. The filtrate was concentrated on rotavacc and the product was purified by column chromatography to afford pure products.

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Reference:
Article; Tekale, Sunil U.; Kauthale, Sushama S.; Pawar, Rajendra P.; Journal of the Chilean Chemical Society; vol. 58; 1; (2013); p. 1619 – 1623;,
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. 4887-88-1, name is 5-Bromo-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H5BrN2

Step C-Methyl 5-(5-bromo-1H-henzimidazol-1-yl)-3-{[tert-butyl(dimethyl)silyl]oxy}thiophene-2-carboxylate and methyl 5-(6-bromo-1H-benzimidazol-1-yl)-3-{[tert-butyl(dimethyl)silyl]oxy}thiophene-2-carboxylate (Title Compounds)To a solution of crude, impure 5-bromobenzimidazole (48.2 g) and methyl 2-chloro-3-oxo-2,3-dihydrothiophene-2-carboxylate (42 g, 220 mmol) in 800 mL of CHCl3 was added N-methylimidazole (28 ml, 350 mmol). After 16 h, N-methylimidazole (17 mL, 220 mmol) and tert-butylchlorodimethylsilane (36 g, 240 mmol) was added. When TLC showed the reaction to be complete, the solution was diluted with water. The layers were separated. The organic phase was washed with water, dried over MgSO4 and concentrated onto celite. The crude mixture was purified by flash column chromatography (0-25% EtOAc:bexanes) in batches to separate the 2 regioisomers, giving 33.5 g of Intermediate 4 eluting first and 29.2 g of Intermediate 5 eluting second (58%). (Intermediate 4, 5-Br) 1H NMR (400 MHz, d6-DMSO) delta 8.77 (s, 1H), 8.01 (d, J=1.6 Hz, 1H), 7.78 (d, J=8.8 Hz, 1H), 7.58(dd, J=8.8 and 1.6 Hz, 1H), 7.25 (s, 1H), 3.78 (s, 3H), 0.99 (s, 9H), 0.27 (s, 6H). (Intermediate 5, 6-Br) 1H NMR (400 MHz, d6-DMSG) delta 8.71 (s, 1H), 7.88 (d, J=1.6 Hz, 1H), 7.73 (d, J=8.8 Hz, 1H), 7.50 (dd, J=8.8 and 2.0 Hz, 1H), 7.26 (s, 1H), 3.77(s, 3H), 0.99 (s, 9H), 0.28 (s, 6H).

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 4887-88-1.

Reference:
Patent; Kuntz, Kevin; Emmitte, Kyle Allen; Rheault, Tara Renae; Smith, Stephon; Hornberger, Keith; Dickson, Hamilton; Cheung, Mui; US2008/300247; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 7189-69-7, name is 1,1′-Sulfonyldiimidazole, molecular formula is C6H6N4O2S, 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. 1,1′-Bis-(3-methyl-imidazole)-1-sulfonyl triflate salt (1-F). To a solution of compound 1-E (1.26 g, 6.36 mmol) in CH2Cl2 (10 mL), cooled to 0 C., was added methyl triflate (0.719 mL, 6.36 mmol). The reaction mixture was allowed to warm to ambient temperature and stirred for 18 hours. The solvent was evaporated under reduced pressure to afford compound 1-F as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7189-69-7, its application will become more common.

Reference:
Patent; Matthews, Jay M.; US2010/160337; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 4856-97-7, 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. 4856-97-7, name is (1H-Benzoimidazol-2-yl)methanol belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a three-necked flask was added 1.24 g (6 mmol) of dicyclohexylcarbodiimide, 0.12 g (lmmol) of 4-dimethylaminopyridine, followed by the addition of 25 mL of tetrahydrofuran. After stirring and stirring, 0. 81 g of indole-3-carboxylic acid (5 mmol) After stirring for half an hour at room temperature, 0.75 g (5 mmol) 2-hydroxymethyl benzimidazole, And then stirred at room temperature for 8h, stop the reaction, filtration, steaming the filtrate, drying, and then dissolved in methylene chloride, room temperature conditions, until a large number of green precipitate precipitation, filtration, filter cake washed, vacuum drying 1.10 g (1H-benzimidazol-2-yl) methyl-1H-indole-3-carboxylate in 90.41percent yield.

The synthetic route of (1H-Benzoimidazol-2-yl)methanol has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Qingdao University of Science & Technology; Kang, Congmin; Wang, XinYing; Liu, yizhou; (5 pag.)CN105315262; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole, 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 4857-06-1, Safety of 2-Chloro-1H-benzo[d]imidazole

General procedure: Alternatively, to a stirred mixture of 2-chlorobenzimidazole (1.0 eq.) and R3CH2Br (1.0 eq.) in dimethylformamide was added N,N-diisopropylethylamine (1.5 eq.). The reaction mixture was heated to 110 C and stirred for 12 h. After the reaction was completed, the reaction mixture was cooled down to room temperature, diluted with ethyl acetate and washed with water. The organic layer was dried over anhydrous MgSO4 and concentrated in vacuo. The crude product was purified by flash column chromatography (ethyl acetate/hexane) to give desired product 1d.

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:
Article; Oh, Sangmi; Kim, Sungbum; Kong, Sunju; Yang, Gyongseon; Lee, Nakyung; Han, Dawoon; Goo, Junghyun; Siqueira-Neto, Jair L.; Freitas-Junior, Lucio H.; Song, Rita; European Journal of Medicinal Chemistry; vol. 84; (2014); p. 395 – 403;,
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. 106429-59-8, name is 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H6N2O2

(d) 5-(2,3-Dihydro-2-oxo-1H-benzimidazol-5-yl)-2,4-imidazolidinedione (20d) 10.7 g (0.0659 mol) of 20c in methanol/water are reacted with 27.8 mol) of ammonium carbonate and 5.2 g (0.107 mol) of sodium cyanide in analogy to Example 1c. Yield: 10 g (65%). C10 H8 N4 O3 (232.2). NMR (DMSO): delta=5.11 (s, 1H), 6.85 (s, 1H), 6.9 (weak d, 2H), 8.36 (s, 1H), 10.68 (s, 3H) ppm.

According to the analysis of related databases, 106429-59-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bayer Aktiengesellschaft; US4748163; (1988); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 312-73-2, name is 2-(Trifluoromethyl)-1H-benzo[d]imidazole, 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 312-73-2, Formula: C8H5F3N2

General procedure: mixtureof benzimidazole derivative (0.01 mol, insoluble in H2O) and correspondingacid (0.01 mol, insoluble in H2O) in absolute methanol (25 ml)was stirred at 65 C for 1-3 h. The solvent was distilled off, and theresidue was multiply washed with diethyl ether and dried (24 h) overP2O5 at ~0.01 Torr to afford viscous liquids or powders (soluble in water).Compounds 14, 15 were prepared by the reaction of ion exchange undersimilar conditions for 7-8 h.

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:
Article; Adamovich, Sergei N.; Mirskova, Anna N.; Mirskov, Rudolf G.; Lopyrev, Valentin A.; Mendeleev Communications; vol. 22; 6; (2012); p. 330 – 331;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem