Category: imidazoles-derivatives

Related Products of 405173-97-9, The chemical industry reduces the impact on the environment during synthesis 405173-97-9, name is 2-(2-Chloroethyl)-1H-benzo[d]imidazole, I believe this compound will play a more active role in future production and life.

General procedure: A mixture of 73 norfloxacin (1.920g, 0.006mol), 97 potassium carbonate (0.830g, 0.006mol) and 98 potassium iodide (0.100g, 0.006mol) in 99 acetonitrile (100mL) was stirred at 50C for 1h. After the mixture was cooled to room temperature, compound 8a (1.000g, 0.006mol) was added. The reaction mixture was then heated at 50C for 3h. After the reaction was completed (monitored by TLC, chloroform/methanol (50/1, V/V)), the reaction was cooled to room temperature and treated with 90 formic acid to adjust the pH value to 5.5-6.5. After the acetonitrile was removed under reduced pressure, the mixture was purified by flash silica gel column eluting with chloroform/methanol (60/1, V/V) to give the pure target 100 compound 13a as white power (1.120g). Yield: 41.7%.

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, 2-(2-Chloroethyl)-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhang, Ling; Addla, Dinesh; Ponmani, Jeyakkumar; Wang, Ao; Xie, Dan; Wang, Ya-Nan; Zhang, Shao-Lin; Geng, Rong-Xia; Cai, Gui-Xin; Zhou, Cheng-He; Li, Shuo; European Journal of Medicinal Chemistry; vol. 111; (2016); p. 160 – 182;,
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. 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 1615-14-1

Example 3; Preparation of Hydroxyethylimidazole Acrylate by Transesterification with Various Catalysts; At a temperature of 60 C., methyl acrylate (MA) and hydroxyethylimidazole (HEI) in a molar ratio of 5:1 were heated in the presence of 50 ppm of phenothiazine, 500 ppm of hydroquinone monomethyl ether and 1.25 mol % of a catalyst (based on hydroxyethylimidazole) for 5 h.After the end of the reaction time, the mixture was analyzed by gas chromatography. The results are compiled in table 2.; It can be seen that, in all cases, the transesterification did not lead to full conversion, since the methanol formed was not removed under the experimental conditions.Consequently, the by-product, according to GC-MS analyses, was the 1,4 addition product of methanol to hydroxyethylimidazole acrylate: Only when Zr(acac)4 was used was a very small amount of by-product formed, since this catalyst virtually completely suppresses this side reaction.It was found that various catalysts such as K3PO4, K2CO3, NaOH, K(acac), Zr(acac)4 and DBU are very suitable for the transesterification of methyl acrylate with hydroxyethylimidazole.

According to the analysis of related databases, 1615-14-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BASF SE; US2010/4462; (2010); 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 1848-84-6 as follows. Safety of 2-Ethyl-1H-benzo[d]imidazole

A mixture of 4-(2-chloro-9-methyl-6-morpholin-4-yl-9H-purin-8-ylmethyl)-3- isopropylpiperazin-2-one (198 mg, 0.49 mmol), 2-ethylbenzimidazole (78 mg, 0.53 mmol), Pd2(dba)3 (11.1 mg, 2.5 molpercent), Xphos (23.1 mg, 10 molpercent) and Cs2CO3 (237 mg, 0.16 mmol) in dioxane (4 mL) was purged with argon gas then heated at 110 0C, for 17 h, in a sealed tube. The reaction mixture was loaded onto an Isolute.(R). SCX-2 cartridge, washed with MeOH then the desired product eluted with 2 M NH3/MeOH in DCM. The resulting residue was purified by column chromatography (Si-PCC, 0-10percent MeOH in EtOAc) to give 648 (196 mg, 78percent) as a white solid. LCMS: (Method I): Rx 3.37 min, [M+H]+ 518.2 1H NMR (400 MHz, CDCl3d): delta 8.05-8.00 (m, 1 H), 7.79-7.75 (m, 1 H), 7.30-7.23 (m, 2 H), 6.02 (s, 1 H), 4.50-3.96 (m, 4 H), 4.09 (d, J = 13.6 Hz, 1 H), 3.94 (d, J = 13.6 Hz, 1 H), 3.89 (s, 3 H), 3.87 (t, J = 4.80 Hz, 4 H), 3.63-3.54 (m, 1 H), 3.37 (q, J = 7.5 Hz, 2 H), 3.34-3.28 (m, 1 H), 3.13-3.04 (m, 1 H), 3.03 (d, J = 5.5 Hz, 1 H), 2.74-2.66 (m, 1 H), 2.25-2.14 (m, 1 H), 1.46 (t, J =7.5 Hz, 3 H), 1.11 (d, J = 6.8 Hz, 3 H), 1.03 (d, J = 6.8 Hz, 3 H)

According to the analysis of related databases, 1848-84-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG; CASTANEDO, Georgette; CHAN, Bryan; GOLDSTEIN, David Michael; KONDRU, Rama K.; LUCAS, Matthew C.; PALMER, Wylie Solang; PRICE, Stephen; SAFINA, Brian; SAVY, Pascal Pierre Alexandre; SEWARD, Eileen Mary; SUTHERLIN, Daniel P.; SWEENEY, Zachary Kevin; WO2010/138589; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 870837-18-6, A common heterocyclic compound, 870837-18-6, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, molecular formula is C12H12N2O2, 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.

Example B7 Preparation of compound 11 A microwave vessel was charged with intermediate 15 (108 mg, 0.5 mmol), 1-phenyl- propane-l,2-dione (74 mg, 0.5 mmol), NH4(OAc) (385 mg, 5 mmol) and AcOH (4 ml). The r.m. was stirred and heated at 160 0C for 7 min. under microwave irradiation. The r.m. was cooled and poured into sat. aq. Na2COs. The mixture was extracted with EtOAc. The o.l. was washed with H2O, brine, and dried (MgSO4). Filtration and concentration gave the crude product which was purified by flash chromatography over silicagel (eluent, 100: 0 to 90:10 DCM/MeOH, gradient elution). The product fractions were collected and evaporated. Yield: 38 mg of compound 11 (22 %).

The synthetic route of 870837-18-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ORTHO-MCNEIL-JANSSEN PHARMACEUTICALS, INC; WU, Tongfei; GIJSEN, Henricus, Jacobus, Maria; ROMBOUTS, Frederik, Jan, Rita; BISCHOFF, Francois, Paul; BERTHELOT, Didier, Jean-Claude; OEHLRICH, Daniel; DE CLEYN, Michel, Anna, Jozef; PIETERS, Serge, Maria, Aloysius; MINNE, Garrett, Berlond; VELTER, Adriana, Ingrid; VAN BRANDT, Sven, Franciscus, Anna; SURKYN, Michel; WO2011/6903; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 3034-50-2, name is Imidazole-4-carbaldehyde, 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 3034-50-2, Computed Properties of C4H4N2O

A 22-L, four-neck, round-bottom flask equipped with a mechanical stirrer, a temperature probe, a condenser, and an addition funnel with a nitrogen inlet was charged with lH-imidazole-4-carboxaldehyde (Aldrich, 1.10 kg, 11.5 mol) and pyridine (3.0 L, 3.0 mol). The reaction flask was cooled to 8 C with an ice bath and hydroxylamine hydrochloride (871 g, 12.5 mol) was added slowly in portions to maintain the internal temperature below 30 C. The reaction was allowed to cool to ambient temperature and stirred for 2 h at ambient temperature. The resulting thick yellow solution was heated to 80 C with a heating mantle and acetic anhydride (2.04 L, 21.6 mol) was added dropwise over 200 min to maintain the temperature below 110 0C during the addition. The reaction EPO mixture was heated at 100 0C for 30 min, after which time it was allowed to cool to ambient temperature and then further cooled in an ice bath. The pH was adjusted to 8.0 (pH meter) by the addition of 25 wt % NaOH (5.5 L) at such a rate that the internal temperature was maintained below 30 C. The reaction mixture was then transferred into a 22-L separatory funnel and extracted with ethyl acetate (6.0 L). The combined organic layer was washed with brine (2 x 4.0 L), dried over MgSO4, filtered, and concentrated to dryness under reduced pressure at 35 0C to give the crude product as a yellow semisolid. The resulting semisolid was suspended in toluene (3.0 L) and stirred for 1 h, after which time it was filtered to give a light yellow solid, which was resuspended in toluene (3.0 L) and stirred for 1 h. The resulting slurry was filtered and the filter cake washed with toluene (2 x 500 mL) to give the title compound as a light yellow solid [870 g, 82%). The 1H and 13C NMR spectra were consistent with the assigned structure.

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; JANSSEN PHARMACEUTICA, N.V.; WO2006/47277; (2006); A2;,
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. 106429-57-6, name is Methyl 2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C9H8N2O3

Potassium tert-butoxide (2.57 g) was added to a solution of 2-oxo-2,3-dihydro-1H-benzoimidazole-5-carboxylic acid methyl ester (2 g) in DMA (30 ml). Allyl bromide (2 ml) was added, and the mixture was stirred for 2 h at room temperature. The mixture was acidified with 2N aqueous HCl and then extracted with EtOAc. The combined organic layers were dried over Na2SO4 and then concentrated to an oil. The residue was purified by flash chromatography (SiO2, EtOAc/heptane 1:2) to give the title compound (2.2 g) as a yellow oil. MS (m/e)=273.2 [M+H+].

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 106429-57-6.

Reference:
Patent; Hunziker, Daniel; Lerner, Christian; Mueller, Werner; Sander, Ulrike Obst; Pflieger, Philippe; Waldmeier, Pius; US2010/249124; (2010); 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. 104619-51-4, name is Di(1H-imidazol-1-yl)methanimine, A new synthetic method of this compound is introduced below., Product Details of 104619-51-4

Example 24: [4-(5-AmJnO- Pl, 3,41 oxadiazot-2-yl)-pyridin-3-yl1-(2-chloro-4-iodo- phenvh-amine; To a solution of 3-(2-Chloro-4-iodo-phenylamino)-isonicotinic acid hydrazide (150mg, 0.39mmol, 1 eq), in DMSO (2mL) C- (Di-imidazol-i-yl)-methyleneamine (124mg, 0.77mmol, 2eq) was added. The reaction mixture was stirred at RT under argon overnight and then poured into water. The product was isolated by filtration (135 mg). LC/MS (Method A) [5.22min; 414(M+1 )]

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; APPLIED RESEARCH SYSTEMS ARS HOLDING N.V.; WO2007/123936; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 33016-47-6,Some common heterocyclic compound, 33016-47-6, name is 1-Trityl-1H-imidazole-4-carbaldehyde, molecular formula is C23H18N2O, 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.

Example 1Under a nitrogen atmosphere, 6-bromo-N-methyl-2- naphthamide (7.0 g, 26.5 mmol) was added to tetrahydrofuran (175 mL) , and then 2.0 mol/L isopropylmagnesium chloridetetrahydrofuran solution (13.7 mL) was added dropwise thereto at room temperature. The reaction mixture was cooled to -30C, 1.6 mol/L n-butyllithium hexane solution (26.6 mL) was added dropwise thereto, and the mixture, was stirred at the same temperature for 2 hr. To the reaction mixture was addeddropwise a solution of l-trityl-4-formyl-lH-imidazole (13.5 g, 39.9 mmol) in tetrahydrofuran (140 mL) at -20C, and themixture was stirred at the same temperature for 2 hr. The reaction mixture was allowed to warm to 0C, and stirred for 1 hr, and 20w/v% aqueous ammonium chloride solution (105 mL) was added dropwise thereto. The organic layer was separated, and concentrated to the volume of about 90 mL under reducedpressure. To the residue was added tetrahydrofuran (140 mL) , and the mixture was concentrated to the volume of about 90 mL under reduced pressure. To the residue was added acetone (140 mL) , and the mixture was concentrated to the volume of about 140 mL under reduced pressure. These operations were repeated three times. To the residue was added acetone to adjust the volume to about 180 mL, and the mixture was stirred at room temperature. The crystals were collected by filtration, and washed with acetone (70 mL) . The obtained wet crystals were dried under reduced pressure to give 6- [hydroxy ( 1-trityl-lH- imidazol-4-yl) methyl] -N-methyl-2-naphthamide (10.3 g, 19.7 mmol) . yield 74%.½ NMR (500 MHz , DMSO-d6) delta 2.84 (d, J = 4.7 Hz, 3H) , 5.76 (d, J = 5.0 Hz, 1H), 5.82 (d, J = 4.7 Hz, 1H) , 6.80 (s, 1H) , 6.98- 7.13 (m, 6H) , 7.28 (d, J = 1.6 Hz, 1H) , 7.32-7.50 (m, 9H) , 7.55 (dd, J = 8.5, 1.6. Hz, 1H) , 7.83-7.99 (m,. 4H) 8.37 (s, 1H) 8.58 (d, J = 4.4 Hz, 1H) ; HRMS (ESI) m/z Calcd for aC35H30 3O2 [M+H] +: 524.2338, Found: 524.2325; Anal. Calcd for a C35H29 3O2: C, 80.28; H, 5.58; N, 8.02. Found: C, 80.17; H, 5.80; N, 7.81.[0097]

The synthetic route of 33016-47-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KAWABATA, Yoichi; SAWAI, Yasuhiro; KANNO, Kazuaki; SAWADA, Naotaka; WO2012/173280; (2012); 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. 52099-72-6, name is 1-(Prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one, A new synthetic method of this compound is introduced below., Recommanded Product: 1-(Prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one

To a solution of 1-isopropenylbenzimidazolone (500 mg, 2.8 mmol) in dry THF (40 mL) are added triphenylphosphine (902 mg, 3.4 mmol) and (4-Methyl-benzo[>]thiophen-3-yl)-methanol (563 mg, 3.2 mmol). Then diisopropyl azodicarboxylate (0.70 mL, 3.4 mmol) is added drop wise into the above solution after it is cooled down to 0 0C. The mixture is then stirred at room temperature for 5 hr and then the solvent is removed under vacuum and the residue is purified by flash column chromatography using gradient EtOAc/Hexane from 0% to 20% to give 630mg (66%) of 1 -isopropenyl-3-(4-methyl-benzo[£]thiophen-3-ylmethyl)- 1 ,3-dihydro-benzimidazol- 2-one.

The synthetic route of 52099-72-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2008/147697; (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 33468-69-8 as follows. Product Details of 33468-69-8

Preparation of 2-[3-ethylsulphanyl-5-(trifluoromethyl)-2-pyridyl]-3-methyl-6-[4-(trifluoromethyl)-imidazol-1-yl]imidazo[4,5-c]pyridine (I-74) Under argon, 99 mg (0.27 mmol) of 6-chloro-2-[3-ethylsulphanyl-5-(trifluoromethyl)-2-pyridyl]-3-methylimidazo[4,5-c]pyridine, 23 mul (0.15 mmol) of trans-N,N’-dimethylcyclohexane-1,2-diamine, 6.8 mg (36 mumol) of copper(I) iodide, 30 mg (0.22 mmol) of 4-(trifluoromethyl)-1H-imidazole and 64 mg (0.46 mmol) of potassium carbonate are added to 1 ml of degassed toluene. The vessel is closed and the reaction mixture is heated in a CEM Discover microwave reactor to 110 C. for 4 h. After cooling to room temperature, ethyl acetate is added and the mixture is filtered through a Celite bed, which is subsequently rinsed with ethyl acetate. The solvent is removed under reduced pressure and the residue is separated chromatographically by MPLC on silica gel (gradient: ethyl acetate/cyclohexane). In this way, 22 mg (100% purity, 18% yield) of 2-[3-ethylsulphanyl-5-(trifluoromethyl)-2-pyridyl]-3-methyl-6-[4-(trifluoromethyl)imidazol-1-yl]imidazo[4,5-c]pyridine are obtained. (log P (neutral): 3.36; MH+: 473; 1H NMR (600 MHz, CD3CN) delta ppm: 8.905 (3.0); 8.903 (3.0); 8.852 (1.6); 8.850 (1.6); 8.500 (1.9); 8.313 (1.5); 8.311 (2.1); 8.309 (1.4); 8.183 (1.7); 8.181 (1.7); 7.962 (3.4); 7.961 (3.4); 4.001 (16.0); 3.940 (0.4); 3.124 (1.1); 3.111 (3.4); 3.099 (3.5); 3.087 (1.2); 2.639 (0.7); 2.184 (55.7); 2.109 (1.2); 2.005 (2.2); 1.998 (195.7); 1.989 (2.7); 1.985 (1.8); 1.981 (10.0); 1.977 (18.2); 1.973 (26.5); 1.969 (18.0); 1.965 (9.0); 1.882 (1.2); 1.419 (0.4); 1.404 (0.7); 1.373 (0.6); 1.330 (4.1); 1.318 (9.0); 1.309 (1.6); 1.305 (5.2); 1.301 (3.4); 0.914 (0.6).

According to the analysis of related databases, 33468-69-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; FISCHER, Ruediger; ALIG, Bernd; ILG, Kerstin; MALSAM, Olga; GOeRGENS, Ulrich; TURBERG, Andreas; LI, Jun; ZHERSH, Sergey; ARLT, Alexander; (58 pag.)US2017/73342; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem