Tag: M.W=200-300

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. 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 144689-93-0

The bromide 2 (58.08 g, 104.18 mmol, 1.0 eq), K2CO3 (18.0 g, 130.23 mmol, 1.25 eq) and KI(0.87 g, 5.21 mmol, 0.05 eq) were added to a solution of the ethyl ester 1 (25.03 g, 104.18 mmol, 1.0 eq)in DMF (230 mL). The reaction mixture was vigorously stirred at room temperature for 24 h.H2O (345 mL) was added dropwise and the resulting suspension was allowed to cool to room temperature while stirring. The solid precipitated was filtered off and washed with H2O (230 mL).The wet-cake was macerated in Me2CO (220 mL) under reflux for 30 min. The mixture was allowedto cool to room temperature. The solid was filtered off, washed with Me2CO (50 mL) and dried in airat room temperature to afford the ethyl ester 3 (62.06 g, 83%).

According to the analysis of related databases, 144689-93-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Dams, Iwona; Ostaszewska, Anna; Puchalska, Maria; Chmiel, Justyna; Cmoch, Piotr; Bujak, Iwona; Bia?o?ska, Agata; Szczepek, Wojciech J.; Molecules; vol. 20; 12; (2015); p. 21346 – 21363;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 1450-93-7, These common heterocyclic compound, 1450-93-7, name is 1H-imidazol-2-amine sulfate(2:1), 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 1 5-(alpha,alpha,alpha-Trifluoro-m-tolyl)imidazo[1,2-a]pyrimidine A mixture of 2.64 g of 2-aminoimidazole hemisulfate, 1.64 g of anhydrous sodium acetate, 4.86 g of 3-dimethylamino-3′-(trifluoromethyl)-acrylophenone and 50 ml of glacial acetic acid was refluxed for six hours. The solvent was removed in vacuo to yield a crude solid. The solid was dissolved in dichloromethane and this solution was washed with saturated aqueous sodium bicarbonate solution. The organic layer was separated and dried over powdered anhydrous sodium sulfate. This solution was passed through a short column of a hydrous magnesium silicate and the effluent was refluxed on a steam bath with the gradual addition of hexane until turbidity was noted. After cooling the desired compound was collected by filtration and gave 1.20 g of pale yellow crystals, m.p. 160-163 C.

Statistics shows that 1H-imidazol-2-amine sulfate(2:1) is playing an increasingly important role. we look forward to future research findings about 1450-93-7.

Reference:
Patent; American Cyanamid Company; US5037980; (1991); A;,
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 150058-27-8 as follows. category: imidazoles-derivatives

To the crude CBME (20 g, 1 eq) obtained in the above-mentioned (3) were added methanol:water [(1:1) (160 mL)] and sodium hydroxide (4.4 g, 3 eq) at 25°C – 30°C, and the reaction mixture was stirred at 75°C – 80°C for 4 hr. Using TLC (TLC: 40percent ethyl acetate/hexane, detection method: UV), complete consumption of CBME was confirmed. The reaction mixture was cooled to 25°C – 30°C, and the organic solvent was evaporated under reduced pressure at 40°C – 45°C. To the concentrated residue was added water (200 mL, 10 vol), and the aqueous layer was washed with t-butyl methyl ether (100 mL, 2×5 vol). The aqueous layer was adjusted to pH 5.5 – 6.5 by adding acetic acid (6 mL, 0.3 vol), the obtained slurry was stirred at 25°C-30°C for 1 hr, and the precipitated solid was filtered. The solid was washed with water (40 mL, 2 vol), dried with suction for 15 min, and further dried at 50°C – 55°C for 4 hr to give crude CBCA (16 g). [0327] To the obtained crude CBCA (16 g) were added ethyl acetate (160 mL, 10 vol) and dicyclohexylamine (DCHA) (8.2 g, 1.5 eq), and the mixture was stirred at 25°C – 30°C for 2 hr. The precipitated solid was filtered, washed with ethyl acetate (80 mL, 5 vol), dried with suction for 15 min, and further blast dried at 50°C – 55°C for 4 hr to give a DCHA salt (16 g) of CBCA. To the salt was added isopropyl alcohol (192 mL, 12 vol) at 25°C – 30°C, and the salt was dissolved by heating to 75°C – 85°C, and the mixture was stirred for 15 min. Thereafter, the reaction mixture was cooled to 25°C – 30°C, and stirred at the same temperature for 2 hr. The precipitated solid was filtered, washed with isopropyl alcohol (32 mL, 2 vol), dried with suction for 15 min, and further blast dried at 50°C – 55°C for 4 hr to give a pure DCHA salt (13 g) of CBCA. To this salt was added 25percent aqueous sodium hydroxide solution (120 mL, 10 vol) at 25°C – 30°C, and the mixture was stirred for 15 min, adjusted to pH 5.5 – 6.5 by adding acetic acid (5.8 mL, 0.48 vol), and extracted with methylene chloride (120 mL, 2×5 vol). The extract was combined with the organic layer, and the mixture was washed with water (120 mL, 2×5 vol) and further with saturated brine (60 mL, 5 vol). The organic layer was dried over sodium sulfate, and concentrated under reduced pressure at 40°C – 45°C to give CBCA (9 g, 47percent from BCL).

According to the analysis of related databases, 150058-27-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; API Corporation; SEKI, Masahiko; EP2891650; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 13275-42-8, name is 2-(2-Bromophenyl)-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 13275-42-8, Quality Control of 2-(2-Bromophenyl)-1H-benzo[d]imidazole

Take a quartz reaction tube, add a magnetic stirrer thereto, and then add 0.3 mmol of 2-(2-bromophenyl)benzimidazole (CAS No. 13275-42-8).0.9 mmol of lithium t-butoxide (t-BuOLi), 20 mmol% of cuprous iodide (CuI), N,N-dimethylformamide (DMF) 1 mL, acetonitrile (CH3CN) 1 mL, and finally 0.6 mmol of benzyl amine. Then add a three-way air guide head with a balloon above the quartz reaction tube.First, the reaction liquid is frozen with liquid nitrogen, and then the quartz reaction tube is evacuated by an oil pump, and then the balloon is filled with nitrogen;Under the stirring of magnetic stirrer, the reaction was carried out under nitrogen conditions and ultraviolet light of 254 nm for 12 hours.Then, it was reacted under air conditions and ultraviolet light of 254 nm for 24 hours, and the reaction was completed.The final product was detected by TLC, and finally the final product, 6-phenylbenzimidazole [1,2-c]quinazoline, was isolated by column chromatography, yield 90%.

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; Henan University; Xu Hao; Liu Yawei; Xu Jing; Wang Yanpeng; Ren Yanrong; Liu Baoying; Zhang Wenkai; Xu Yuanqing; Fang Xiaomin; Ding Tao; (10 pag.)CN108610345; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, 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 641571-11-1, COA of Formula: C11H10F3N3

General procedure: To a solution of chloroanhydride in dry CHCl3 was addedamine R2NH2 (one equivalent) and Et3N (1.5 equivalents). The reaction mixture was stirred atroom temperature. The reaction progress was monitored by TLC. Cold water was added to thereaction mixture. The organic layer was separated from the water. The combined organic layers weredried over Na2SO4, filtered, and concentrated under vacuum. The product was purified by columnchromatography on silica gel.

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, 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kalinichenko, Elena; Faryna, Aliaksandr; Kondrateva, Viktoria; Vlasova, Alena; Shevchenko, Valentina; Melnik, Alla; Avdoshko, Olga; Belko, Alla; Molecules; vol. 24; 19; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 4499-07-4,Some common heterocyclic compound, 4499-07-4, name is 2-(1H-Benzo[d]imidazol-2-yl)ethanamine dihydrochloride, molecular formula is C9H13Cl2N3, 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.

The ligand L1 was synthesized by a condensation reaction between 2-aminoethyl-1H-benzimidazole dihydrochloride (1.170g, 5mmol), previously neutralized with K2CO3 (0.828g, 6mmol), and pyridine-2-carbaldehyde (0.535g, 5mmol) in 25mL of methanol. The reaction mixture was stirred at room temperature for approximately 2h. The resulting brown solution was removed on a rotatory evaporator and the light brown product was then filtered and recrystallized from EtOH for two times. Yield: 1.06g (85%). m.p.: 155-156C. IR (KBr pellet, cm-1): 1635(nuC=N), 1437(nuC=C-C=N). 1H NMR (500MHz, DMSO-d6, ppm) delta: 3.22-3.25 (t, 2H, -CH2-), 4.05-4.08 (t, 2H, -CH2-), 7.42-8.97 (m, 8H, Ar-H), 8.98 (s, 1H, -CH=N-), 12.61 (br s, 1H, NH). UV-Vis (methanol, lambdamax, nm): 204, 248, 276, 281. Anal. Calc. for C15H14N4: C, 71.98; H, 5.64; N, 22.38. Found: C, 71.86; H, 5.57; N, 22.29%.

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

Reference:
Article; Zhao, Hai-Yan; Yang, Fu-Li; Li, Na; Wang, Xiao-Jing; Journal of Molecular Structure; vol. 1148; (2017); p. 62 – 72;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 1450-93-7, 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. 1450-93-7, name is 1H-imidazol-2-amine sulfate(2:1), This compound has unique chemical properties. The synthetic route is as follows.

2-Aminoimidazole sulfate (659 mg) is dissolved in 0.42 mL of concentrated HCl, 1 mL of water, and 3 mL of acetic acid. The resulting solution is cooled to 0 C. To the solution is added 345 mg of NaNO2 in 1 mL of water dropwise so the internal temperature is maintained below 5 C. The resulting yellow-brown solution is stirred for 30 minutes at 0 C. In a separate flask equipped with a mechanical stirrer a mixture of 1.0 g of 2,2,2-trifluoro-1-(4-pentyl-3,4-dihydroquinoxalin-1(2H)-yl)ethan-1-one, 0.82 g of sodium acetate and 3 mL of acetic acid is cooled to 0 C. To this slurry is added the diazonium solution slowly while stirring. After the addition is complete, the resulting red suspension is stirred for 1 hour at 0 C. The dark reaction mixture is poured into a beaker containing 10 g of ice. Aqueous NaOH (20%) is added to the suspension slowly until pH 6.5 is reached. The mixture is filtered and brick red solid is collected. The crude (E)-1-(7-((1H-imidazol-2-yl)diazenyl)-4-pentyl-3,4-dihydroquinoxalin-1(2H)-yl)-2,2,2-trifluoroethan-1-one is dried and used in the next step without further purification (0.94 g).

The chemical industry reduces the impact on the environment during synthesis 1H-imidazol-2-amine sulfate(2:1). I believe this compound will play a more active role in future production and life.

Reference:
Patent; The Procter & Gamble Company; MURPHY, Bryan Patrick; ZHANG, Guiru; ZHAO, Jielu; (32 pag.)US2018/72970; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 10351-75-4, 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. 10351-75-4, name is 1H-Benzo[d]imidazole-5,6-dicarboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

2.2.1 H24-DPBB A mixture of benzimidazole-5,6-dicarboxylic acid (2.0616 g, 10 mmol) and 4-aminobenzoic acid (1.3714 g, 10 mmol) in 30 ml DMF was heated at 135 C for 10 h, then filtrated. The product was washed several time with hot DMF and EtOH, then dried in air. Yield: 70%. Element analysis (%): Anal. Calc. for C16H9N3O4: C 62.54, H 2.95, N 13.68. Found: C 62.55, H 2.91, N 13.65%. IR (KBr pellet, cm-1): 3340(m), 3050(s), 1770(m), 1713(vs), 1605(m), 1509(m), 1371(vs), 1264(vs), 1118(m), 865(s), 835(s), 610(s). Negative ESI-MS (m/z): 305.98 (H24-DPBB-H+). 1H NMR (DMSO-d6): delta: 7.630 (J = 4.8 Hz, d, 2H, Ph-H), 8.097 (J = 1.2 Hz, d, 2H, Ph-H), 8.114 (s, 1H, Ph-H), 8.208 (s, 1H, Ph-H), 8.602 (s, 1H, Im-H), 13.320 (s, 1H, COOH). Melting points: above 300 C.

The chemical industry reduces the impact on the environment during synthesis 1H-Benzo[d]imidazole-5,6-dicarboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Article; Yang, Jing-Si; Zhu, Jiang; Liu, Rui-Bin; Ni, Jun; Chang, Zhi-Duo; Hu, Tao; Zhang, Jian-Jun; Meng, Chang-Gong; Inorganica Chimica Acta; vol. 394; (2013); p. 117 – 126;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 870837-18-6, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, 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 870837-18-6, name: 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde

Under ice-cooling, L-selectride (3.73 mL, 1.02 M tetrahydrofuran solution) was added dropwise into a tetrahydrofuran (25 mL) solution containing (4R,6S)-6-(4-chlorophenyl)-1,1-dimethyltetrahydropyrrolo[2,1-c][1,4]oxazine-3,4-dione (850 mg). Stirring was continued for 1 hour at the same temperature. A 5 N sodium hydroxide solution (566 muL) was added to the reaction solution, and stirring was continued for 20 minutes at 0 C. Next, hydrogen peroxide solution (275 muL, 35% solution) was added, and stirring was continued for 20 minutes at 0 C. Sodium bisulfite (294 mg) was added, and after stirring for 20 minutes at room temperature, ethyl acetate and brine were added, and the organic layer was partitioned. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under a vacuum. Acetonitrile (25 mL) and triphenyl phosphonium bromide (990 mg) was added to the residue, and the resultant was heated under reflux for 1 hour. The resultant was returned to room temperature, and 3-methoxy-4-(4-methyl-1H-imidazol-1-yl) benzaldehyde (674 mg) and triethylamine (781 muL) were added, and stirring was continued for 10 hours at room temperature. Ethyl acetate and brine were added, and the organic layer was partitioned. The resultant was dried over anhydrous magnesium sulfate, and the solvent was removed under a vacuum, and ethyl acetate (1 mL) was added to the residue, and diethyl ether (15 mL) was added gradually, and the precipitated solid was collected by filtration, and the title compound (790 mg) was obtained. The physical property values are as follows.ESI-MS; m/z 478 [M++H]. 1H-NMR (CDCl3) delta(ppm): 1.45 (s, 3H), 1.58 (s, 3H), 1.81-1.92 (m, 1H), 2.02-2.14 (m, 2H), 2.29 (s, 3H), 2.34-2.45 (m, 1H), 3.85 (s, 3H), 3.94 (dd, J=11.6, 5.2 Hz, 1H), 5.14 (d, J=9.2 Hz, 1H), 6.78 (s, 1H), 6.91 (s, 1H), 7.18 (d, J=8.0 Hz, 1H), 7.24-7.32 (m, 5H), 0.53 (d, J=9.6 Hz, 1H), 7.69 (d, J=1.6 Hz, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; KIMURA, Teiji; Kawano, Koki; Doi, Eriko; Kitazawa, Noritaka; Takaishi, Mamoru; Ito, Koichi; Kaneko, Toshihiko; Sasaki, Takeo; Sato, Nobuaki; Miyagawa, Takehiko; Hagiwara, Hiroaki; US2008/207900; (2008); 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. 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: 144689-93-0

Example 3; Preparation of olmesartan medoxomilTo dimethyl acetamide (800 ml) was added 4-(1-hydroxy-1-methylethyl)-2-propyl imidazol- 5-carboxylic acid ethyl ester (100 gms) and powdered potassium carbonate (200 gms). To this was charged 4-[2-(trityltetrazol-5-yl)phenyl]benzyl bromide (300 gms) at 45-50C. The contents were stirred for 8-10 hours at 45-50C. The insolubles were filtered. The contents were cooled to 5-100C. Potassium tertiary butoxide (100 gms) was charged at a temperature below 45C. The reaction was maintained at 40-450C for 3 hrs. To this was slowly added 5-methyl-2-oxo-1 ,3-dioxane-4-yl) methyl chloride at 40-450C over a period of 1 hour. The contents were heated to 60-650C and maintained for 4 hours. The reaction mass was then cooled to 30-350C and was neutralized with concentrated hydrochloride acid. The reaction mass was filtered to remove inorganics. The reaction mass was charcoalized using charcoal (10 gms) and was stirred for 30 minutes at 40-450C. The reaction mass was filtered over hyflo. The clear filtrate was acidified with hydrochloric acid (100 ml) slowly at 25-30C. The contents were stirred at 60C for 1 hour. The reaction mass was chilled to 0-5C and was filtered to remove tritanol. The reaction mass was concentrated under reduced pressure. The residue was quenched with water (500 ml), neutralized with base and extracted in dichloromethane (500 ml).The clear dichloromethane extract was then concentrated under reduced pressure, stripped off with acetone. The residue thus obtained was isolated from the acetone (250 ml) to give 55 gms of the title compound. Chromatogrphic purity- > 99%

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; CIPLA LIMITED; CURTIS, Philip, Anthony; WO2008/43996; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem