Tag: M.W=200-300

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. 13275-42-8, name is 2-(2-Bromophenyl)-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., Safety of 2-(2-Bromophenyl)-1H-benzo[d]imidazole

General procedure: First, 100 mmol of 2-(2-bromophenyl)imidazole derivatives introduced into 300 ml of triethylamine and 200 ml of DMF. And stirring continuously added to 200 ml alkyne, 5 mmol triphenylphosphine and 5 mmol of copper iodide (I) and 2 mmol palladium(II) acetate. The reaction mixture was then stirred for 20 hours at 80 . After cooling, the reaction mixture was diluted with 400 ml of methylene chloride, to separate a solid, by filtration through a bed of salt C and the filtrate was evaporated to dryness. The residue was dissolved in 300 ml of methylene chloride, 100 ml of concentrated aqueous ammonia with individual cleaning solution three times, and then washed three times with 100 ml of water, and dried over magnesium sulfate. With spherical fractionating tube distillation or sublimation, resulting in the manipulation of the vacuum pump oil / solids release low-boiling components and trace metals.

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; MERCK PATENT GMBH; STOESSEL, PHILIPP; HEIL, HOLGER; JOOSTEN, DOMINIK; PFLUMM, CHRISTOF; GERHARD, ANJA; BREUNING, ESTHER; (214 pag.)TWI520958; (2016); B;,
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Imidazole | C3H4N2 – PubChem

Related Products of 641571-11-1, 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. 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A suspension of 1 (0.10 g, 0.40 mmol), 51 (0.13 g, 0.54 mmol), Pd2(dba)3 (25 mg, 0.027 mmol), t-tert-buty phosphine (IM in toluene; 0.1 mL, 0.10 mmol) and potassium tert- butoxide (0.25 g, 2.2 mmol) in dioxane/DMF (1/1; 6 mL) was sealed in a microwave reaction tube and irradiated with microwave at 160 0C for 30 min. After cooling to room temperature, the resulting mixture was filtered and the filtered solid washed with DCM. The filtrate was concentrated and the residue purified by HPLC. The fractions were combined and poured into saturated NaHCO3 solution (20 mL). The combined aqueous layers were extracted withEtOAc (2 x 20 mL) and the combined organic layers washed with brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated and the residue re-dissolved in minimum amount of EtOAc and hexanes added until solid precipitated. After filtration, the title compound was obtained as a light brown solid (23 mg, 13%).[0264] 1K NMR (500 MHz, DMSO-J6): delta 2.20 (s, 3H), 2.33 (s, 3H), 6.93 (dd, J = 3.6, 1.7 Hz, IH), 7.41 (dd, J = 3.6, 2.3 Hz, IH), 7.44 (s, 2H), 7.50 (s, IH), 7.97 (s, IH), 8.20 (d, J = 0.8 Hz, IH), 8.27 (s, IH), 8.46 (s, IH), 11.84 (s, IH)MS (ES+): m/z 455 (M+H)+

The synthetic route of 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TARGEGEN INC.; WO2009/49028; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

14741-71-0, name is Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate, 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. Computed Properties of C11H12N2O2

General procedure: To the dry solid of compound 3 (2.04 g, 0.01 mol) ammonium acetate (0.50 g) eithercyclophentanone (0.78 g, 0.01 mol) or cyclohexanone (0.92 g, 0.01 mol) were added. Thereaction mixture was heated in an oil bath at 120 oC for 1 h then left to cool. The product wastriturated with ethanol and the formed solid product was collected by filtration.Ethyl 2-(1H-benzo[d]imidazol-2-yl)-2-cyclopentylideneacetate (15a). Pale yellow crystals fromethanol; yield: 2.53 g (83%); m.p. 155 oC. IR, : 3459-3322 (NH), 3053 (CH aromatic), 2929,2863 (CH3, CH2), 1686 (CO), 1636 (C=N), 1630 (C=C). 1H-NMR: : 1.13 (t, 3H, J = 6.93 Hz,CH3), 1.18-1.24 (m, 4H, 2CH2), 2.19-2.21 (m, 4H, 2CH2), 4.22 (q, 2H, J = 6.93 Hz, CH2), 7.27-7.38 (m, 4H, C6H4), 8.32 (s, 1H, NH, D2O exchangeable). 13C NMR (DMSO): 16.2 (ester CH3),1.89-2.13 (2m 4CH2), 52.6 (ester CH2), 86.4, 90.6 (C=C), 120.3, 121.2, 123.2, 125.6, 128.6(C6H4), 164.8 (CO), 173.2 (C=N); Anal. calcd for C16H18N2O2: C, 71.09; H, 6.71; N, 10.36%.Found: C, 70.93; H, 6.93; N, 10.47%. MS: m/z: (%) 270 (M+, 36%).

The synthetic route of 14741-71-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mohareb, Rafat M.; Gamaan, Marwa S.; Bulletin of the Chemical Society of Ethiopia; vol. 32; 3; (2018); p. 541 – 557;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 213133-77-8, These common heterocyclic compound, 213133-77-8, name is 2-(3,4-Dichlorobenzyl)-1H-benzo[d]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: To a stirred solution of 2-phenyl-1H-benzo[d]imidazole 7a (50 mg, 0.26 mmol) and NaH (7 mg, 0.31 mmol) in DMF (0.5 mL) was added methyl bromoacetate (29 muL, 0.31 mmol) dropwise. After stirring at room temperature for 16 h, the reaction mixture was extracted with EtOAc (3 ~ 20 mL) and washed with H2O (~ 20 mL). The organic layer was dried over anhydrous MgSO4, and concentrated in vacuo. The residue was purified by column chromatography (SiO2, n-hexane/EtOAc 2/1) to yield the title product 8a (35 mg, 50%).

The synthetic route of 213133-77-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kim, TaeHun; Yang, Ha Yun; Park, Beoung Gun; Jung, Seo Yun; Park, Jong-Hyun; Park, Ki Duk; Min, Sun-Joon; Tae, Jinsung; Yang, Hyejin; Cho, Suengmok; Cho, Sung Jin; Song, Hyundong; Mook-Jung, Inhee; Lee, Jiyoun; Pae, Ae Nim; European Journal of Medicinal Chemistry; vol. 125; (2017); p. 1172 – 1192;,
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 1243204-92-3 as follows. Quality Control of 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzonitrile

[0428] To a stirred solution of 3-methoxy-4-(4-methyl-1H-imidazol-1-yl) benzonitrile (450 mg, 2 mmol) in MeOH (23 mL) at room temperature under an argon atmosphere were added hydroxyl amine hydrochloride (230 mg, 2 mmol) and sodium bicarbonate (230 mg, 3 mmol). The reaction mixture was stirred at 85 C for 3 h. After consumption of starting material (by TLC), the volatiles were evaporated in vacuo. The residue was diluted with ice cold water (50 mL), stirred for 10 mm, to obtain the solid. The solid was collected by filtration and dried in vacuo to obtain (Z)-iV-hydroxy-3-methoxy-4-(4-methyl-1H-imidazol-1- yl) benzimidamide (450 mg, 88%) as an off-white solid.?H NMR (DMSO-d6, 500 MHz): 9.73 (s, 1H), 7.79 (s, 1H), 7.47 (s, 1H), 7.37 (s, 2H), 5.92 (s, 2H), 3.82 (s, 3H), 2.15 (s, 3H); LCMS: 92.4%; 247 (M+1); (column; X-select CSH C-18 (50 x 3.0 mm, 2.7 tim); RT 2.06 mm; mobile phase: 2.5mM NH400CH in water+5% ACN:ACN+5% 2.5mM NH400CH in water; T/B%: 0.01/5, 0.5/5, 3/100, 5/100; flow rate: 1.2 mL/min) (Gradient); TLC: 3% MeOH/CH2C12 (R1: 0.3).

According to the analysis of related databases, 1243204-92-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; HARRISON, Bryce, Alden; (273 pag.)WO2017/31325; (2017); 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. 10040-96-7, name is 1-(4-Bromophenyl)imidazole, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 10040-96-7

Pd(PPh3)4 (112 mg, 96.7 mumol) was added to a mixture of 6 (600 mg, 0.967 mmol) and 1-(4-bromophenyl)-1H-imidazole (863 mg, 3.87 mmol) in aqueous Na2CO3 (2 M, 2.0 mL, 4.0 mmol) and anhydrous THF (18.0 mL), and the solution was stirred at room temperature for 15 min. The resulting two-phase system was refluxed under stirring overnight, and was then allowed to cool to room temperature. To this was added water (50 mL), and the mixture was extracted with CHCl3 (100 mL¡Á3). The organic layer was washed with water (50 mL), dried over anhydrous MgSO4, and filtered. After the solvent was removed by evaporation, the residue was subjected to SEC fractionation to obtain 2 (516 mg, 79%) as a bluish white solid. Mp: 251.8-252.0 C. IR (KBr, cm-1): 1523, 1305, 1273, 1139, 1114, 1055, 989. 1H NMR (500 MHz, CDCl3): delta 7.89 (s, 2H, ArH), 7.65 (d, J=8.6 Hz, 4H, PhH), 7.42 (d, J=8.6 Hz, 4H, PhH), 7.32 (s, 2H, ArH), 7.25 (s, 2H, ArH), 2.01 (s, 6H, CH3). 13C NMR (125 MHz, CDCl3): delta 142.1, 140.9, 136.9, 135.6, 132.7, 130.9, 127.1, 126.2, 123.1, 122.0, 118.2, 14.8. MS (ESI+): m/z=653 [M+H]+. Anal. Calcd for C33H22F6N4S2: C, 60.73; H, 3.40; N, 8.58. Found: C, 60.74; H, 3.48; N, 8.45.

According to the analysis of related databases, 10040-96-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Iida, Hiroki; Umebayashi, Naofumi; Yashima, Eiji; Tetrahedron; vol. 69; 52; (2013); p. 11064 – 11069;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 14741-71-0,Some common heterocyclic compound, 14741-71-0, name is Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate, molecular formula is C11H12N2O2, 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: To a solution of compound 3 (2.04 g, 0.01 mol) in dimethylformamide (30 mL) either aniline(0.93 g, 0.01 mol) or 4-methylaniline (1.08 g, 0.01 mol) was added. The reaction mixture, ineach case, was heated under reflux for 4 h then poured onto ice/water mixture containing fewdrops of hydrochloric acid and the formed solid product was collected by filtration. 2-(1H-Benzo[d]imidazol-2-yl)-N-phenylacetamide (5a). Light brown crystals from ethanol;yield: 2.08 g (80%); m.p. 220-222 oC. IR, : 3472-3324 (2NH), 3050 (CH aromatic), 1680(C=O), 1648 (C=N), 1629 (C=C). 1H-NMR, : 4.93 (s, 2H, CH2), 7.25-7.41 (m, 9H, C6H5,C6H4), 8.26, 8.32 (2s, 2H, 2NH, D2O exchangeable). 13C NMR (DMSO): 54.8 (CH2), 119.2,120.8, 122.8, 123.6, 124.3, 125.2, 126.1, 127.3, 128.3, 129.2, (C6H5, C6H4), 164.8 (CO), 172.4(C=N); Anal. calcd for C15H13N3O: C, 71.70; H, 5.21; N, 16.72%. Found: C, 71.83; H, 5.08; N,16.82%. MS: m/z: (%) 251 (M+, 24%).

The synthetic route of 14741-71-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mohareb, Rafat M.; Gamaan, Marwa S.; Bulletin of the Chemical Society of Ethiopia; vol. 32; 3; (2018); p. 541 – 557;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 1231930-33-8, These common heterocyclic compound, 1231930-33-8, name is 6-Bromo-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]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.

DMSO (100 mL) was added to a 500 mL one-necked flask and the compound of formula XVI-1 (20.0 g,73.80 mmoL), bis (pinacolato) diboron (27.6 g, 108.69 mmol), tricyclohexylphosphine (3.53 g, 12.61 mmol)Potassium acetate (21.3 g, 217.38 mmol). Nitrogen gas was added to the reaction flask after the rapid addition of palladium acetate (1.5g), nitrogen PaulProtect the next open heating to 90C. After 3 hours the reaction flask was cooled to room temperature and the reaction mixture was poured into 700 mL of water, mixed thoroughly and subtractedPressure filtration, the filter cake was washed twice with 100mL of water and dried to give a light brown solid. Crude was added 50mL petroleum ether, 10mL BEthyl acetate beating 10min, vacuum filtration to give a white solid (18.8g, yield 80.3%)

The synthetic route of 1231930-33-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhengda Tianqing Pharmaceutical Group Co., Ltd.; Zhang Yinsheng; Liu Yingshuai; Qin Hui; Li Yuan; Zhao Kaidi; Miao Lei; Hu Jie; Liu Haiyan; Wang Xiaojin; (33 pag.)CN107266421; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 26576-46-5, name is 5-Acetoacetlamino benzimdazolone, 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 26576-46-5, Formula: C11H9N3O3

Into a 250 mL round bottom flask is charged anthranilic acid (6.0 g, available from Sigma-Aldrich, Milwaukee, Wis.), deionized water (80 mL) and 5M HCl aqueous solution (20 mL). The mixture is stirred at room temperature until all solids are dissolved, then cooled to 0 C. A solution of sodium nitrite (3.2 g) is dissolved in deionized water (8 mL) and then is added dropwise into the solution of anthranilic acid at a rate that maintains the internal temperature range in the mixture of 0-5 C. Once diazotization is complete, the solution is stirred an additional 0.5 hr. Prior to coupling reaction, any excess nitrite ion is destroyed using aliquots of dilute aqueous urea solution. A second mixture for the coupling component is prepared by charging deionized water (100 mL) and sodium hydroxide (5.5 g) into a 500-mL vessel, stirring to dissolution, then adding 5-(acetoacetamido)-2-benzimidazolone (10.5 g, available from TCI America, Portland, Oreg.) into this solution while vigorously stirring until all solids dissolved. A separate solution containing glacial acetic acid (15 mL), 5M NaOH solution (30 mL) and deionized water (200 mL) is then added dropwise into the alkaline solution of coupling component while stirring vigorously, after which the coupling component is precipitated as a white suspension of particles, and the mixture is weakly acidic. For coupling reaction, the chilled diazotization mixture is slowly added dropwise into the suspension of coupling component, while stirring vigorously, to produce a reddish-yellow slurry of pigment. The slurry is stirred at room temperature for another 2 hours, after which time the pigment is isolated by vacuum-filtration, is washed with several volumes of deionized water (3 portions of 250 mL), then freeze-dried. Reddish-yellow granules of pigment are obtained, and TEM images show large aggregates of rod-shaped particles having high aspect ratio, with particle diameters ranging from 200 to 500 mm.

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; Xerox Corporation; US7503973; (2009); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 857035-29-1, 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. 857035-29-1, name is Ethyl 2-chloro-1H-benzo[d]imidazole-6-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

LiAlH4 (0. 146 mol) was added portion wise to a solution of tetrahydrofuran (200 ml) at 5C under N2 flow. A solution of b-1 (0.073 mol) in tetrahydrofuran (200 ml) was then added drop wise. The mixture was stirred at 5C for 3 hours. A minimum of H20 was then added, followed by a solution of CH2Cl2/CH30H (90/10). The resulting mixture was dried (over MgSO4), filtered and the solvent was evaporated until dryness, yielding 12.6 g of intermediate b-2 (95%, melting point: 179C).

The synthetic route of Ethyl 2-chloro-1H-benzo[d]imidazole-6-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD.; WO2005/58871; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem