Month: June 2021

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

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

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

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

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

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

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 492-98-8 as follows. Formula: C6H6N4

A mixture of CuCl22H2O (0.068 g, 0.40 mmol), K3[Fe(CN)6](0.099 g, 0.30 mmol) and 2,20-biimidazole (0.101 g, 0.75 mmol)in H2O (7 ml) was stirred for 15 min at room temperature,then sealed in a 15 ml Teflon-lined stainless steel containerand heated to 433 K for 6 d. After it had been cooled to roomtemperature at a rate of 10 K h1, red block-shaped crystalswere obtained in 40% yield (based on Cu). Analysis calculated(%) for C4H3CuN3, (I): C 30.67, H 1.93, N 26.82; found: C 30.46, H 1.85, N 26.95. IR (KBr, pellet, cm1): (N-H) 3448(w), (C-H) 3318 (w), (C N) 2108, 2042 (s), (C C andC N) 1526 (m).

According to the analysis of related databases, 492-98-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Qin, Ying-Lian; Sun, Hong; Jing, Yan; Jiang, Xiu-Ping; Wang, Gao-Feng; Qin, Jian-Fang; Acta Crystallographica Section C: Structural Chemistry; vol. 75; (2019); p. 1517 – 1523;,
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 33543-78-1 as follows. category: imidazoles-derivatives

4-Benzylcarbamoyl-2-(ethoxycarbonylimidazolyl)-1-indanone can be prepared in the following way: a mixture of 0.5 g of 4-benzylcarbamoyl-2-bromo-1-indanone, 0.37 g of 2-ethoxycarbonylimidazole and 10 ml of toluene is heated at reflux for 12 hours. The reaction mixture is concentrated on a rotary evaporator. Dichloromethane is added to the evaporation residue, filtration is carried out and the filtrate is washed with distilled water, dried over sodium sulphate and evaporated on a rotary evaporator. The brown oil obtained (0.26 g) is purified by chromatography on a silica column (diameter: 1.5 cm, height: 30 cm), elution being carried out with a dichloromethane/methanol (95/5 by volume) mixture. The foamy product obtained is triturated with 5 ml of ethyl acetate, filtered and the solid is washed with ethyl acetate (2*5 ml) and dried at 50° C. under vacuum (1 mm Hg; 0.13 kPa). 0.07 g of 4-benzylcarbamoyl-2-(2-ethoxycarbonylimidazolyl)-1-indanone is obtained in the form of an orange solid melting at 218° C. 4-Benzylcarbamoyl-2-bromo-1-indanone can be prepared in the following way:

According to the analysis of related databases, 33543-78-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Rhone-Poulenc Rorer S.A.; US5902803; (1999); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 2302-25-2, A common heterocyclic compound, 2302-25-2, name is 4-Bromo-1H-imidazole, molecular formula is C3H3BrN2, 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.

[00622] To a solution of 197-2c (1.0 g, 6.8 mmol, 1.0 eq) in DMF (10.0 mL) was added K2C03 (1.4 g, 10.2 mmol, 1.5 eq) and 197-2b (1.2 g, 7.4 mmol, 0.8 mL, 1.1 eq). The mixture was stirred at 80 C for 2 h. TLC indicated 20% of 197-1 was remained, and one major new spot with lower polarity was detected. The reaction mixture was diluted with H20 (20.0 mL), extracted with EtOAc (10.0 mL * 3). The combined organic layers were washed with brine (30.0 mL), dried over Na2S04, filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (Si02) to give 197-2a (500.0 mg, 2.1 mmol, 31% yield). 1HNMR (400 MHz, CDC13) 7.38 (s, 1H), 6.94 (s, 1H), 4.69-4.61 (m, 2H), 4.30-4.20 (m, 3H), 1.35-1.26 (m, 3H).

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; VIVACE THERAPEUTICS, INC.; KONRADI, Andrei W.; LIN, Tracy Tzu-Ling Tang; (396 pag.)WO2018/204532; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 4857-06-1,Some common heterocyclic compound, 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole, molecular formula is C7H5ClN2, 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 275A 2-chloro-1-methyl-1H-benzo[d]imidazole To a solution of 2-chloro-1H-benzo[d]imidazole (2.0 g, 13.1 mmol) in DMF (10 mL) was added NaH (0.63 g, 15.7 mmol) at 0 C. under N2. After stirring for 30 min at 0 C., iodomethane (5.58 g, 39.3 mmol) was added and the mixture was stirred at room temperature for additional 1 hour. The reaction mixture was quenched with water (100 mL). The aqueous layer was extracted with EtOAc (3*20 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated to give the title compound (1.9 mg, 8.9 mmol, 67.9% yield) as a white solid. MS: MS (M+H)+; 1H NMR (400 MHz, CDCl3): delta 7.71-7.68 (m, 1H), 7.31-7.27 (m, 3H), 3.79 (s, 3H).

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

Reference:
Patent; AbbVie Inc.; Bayburt, Erol K.; Clapham, Bruce; Cox, Phil B.; Daanen, Jerome F.; Dart, Michael J.; Gfesser, Gregory A.; Gomtsyan, Arthur; Kort, Michael E.; Kym, Philip R.; Schmidt, Robert G.; Voight, Eric A.; US2013/131036; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem