Tag: M.W=300-400

15469-97-3, name is 1-Trityl-1H-imidazole, 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. Recommanded Product: 15469-97-3

n-butyllithium (1.6M hexane solution, 6.9ml) was added dropwise to a solution of 1-tritylimidazole (3.10g) in THF (80mL) under ice-cooling in the argon atmosphere. After stirred at the same temperature for 30 minutes, (R)-2-[(benzyloxy)methyl]oxirane (1.52mL) was added. After stirred for 1.5 hours under ice-cooling and at room temperature for 1 hour, water was added to the reaction solution, followed by ethyl acetate. The extract was washed with water and a brine, dried with magnesium sulfate, and concentrated under reduced pressure. The residue was purified by subjecting to the silica column gel chromatography (eluent; ethyl acetate_hexane= 1:1) to obtain the title compound (1.402g) as a pale yellow oil. 1H-NMR (CDCl3) delta: 2.06 (2H, dd, J = 2.8Hz, 18.0Hz), 3.08 (1H, dd, J = 5.4Hz, 9.8Hz), 3.21 (1H, dd, J = 5.4Hz, 9.8Hz), 3.55-3.7 (1H, m), 4.36 (2H, s), 6.73 (1H, d, J = 1.4Hz), 6.93 (1H, d, J = 1.4Hz), 7.0-7.4 (20H, m).

The synthetic route of 15469-97-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1350792; (2003); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 15469-97-3, 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. 15469-97-3, name is 1-Trityl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A. 2-Hydroxyethyl-N-triphenylmethylimidazole To a solution of N-triphenylmethylimidazole (15.5 g, 50 mmol) at 0°C in THF was added normal butyl lithium (nBuLi) (34.4 mL, 55 mmol) dropwise over 30 minutes. The mixture was stirred for 1 hour followed by gentle warming to 30°C over 30 minutes. The solution was cooled to 0°C, and ethylene oxide (24.4 mL, 50 mmol) was added to the mixture via a cannula. The mixture was stirred at 0°C for 2 hours and gradually warmed to ambient temperature over 16 hours. The solution was concentrated and the residue was chromatographed (flash silica, 19:1; chloroform:methanol) to yield 14.5g (82percent) of compound A as a white solid. MS (M+Na)+ 377+.

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, 1-Trityl-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; EP675112; (1995); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 15469-97-3, 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. 15469-97-3, name is 1-Trityl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A. 2-Hydroxyethyl-N-triphenylmethylimidazole To a solution of N-triphenylmethylimidazole (15.5 g, 50 mmol) at 0°C in THF was added normal butyl lithium (nBuLi) (34.4 mL, 55 mmol) dropwise over 30 minutes. The mixture was stirred for 1 hour followed by gentle warming to 30°C over 30 minutes. The solution was cooled to 0°C, and ethylene oxide (24.4 mL, 50 mmol) was added to the mixture via a cannula. The mixture was stirred at 0°C for 2 hours and gradually warmed to ambient temperature over 16 hours. The solution was concentrated and the residue was chromatographed (flash silica, 19:1; chloroform:methanol) to yield 14.5g (82percent) of compound A as a white solid. MS (M+Na)+ 377+.

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, 1-Trityl-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; EP675112; (1995); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 760212-58-6, 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. 760212-58-6, name is 1-(4-Bromophenyl)-2-phenyl-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step S101: 2-phenyl-4-N-p-bromophenylbenzimidazole was dissolved in THF (tetrahydrofuran); preferably,In the step, 2-phenyl-4-N-p-bromophenylbenzimidazole was 1. Ommol, THF (tetrahydrofuran)Step S102: cooling to -78 C, adding n-butyllithium, for one hour; preferably, n-butyllithium is 1 · lmmol in this step;Step S103: Diphenylphosphonium chloride is added and the temperature is raised to room temperature for 12 hours. Preferably, diphenylphosphonium chloride is 1.2 mmol in this step;Step S104; adding a methanol quenching reaction while adding 30% H2O2 aqueous solution to give 4- (1-methylbenzimidazolyl) -triphenylphosphine oxide; preferably, 30% H2O2 aqueous solution in this step is 5 ml ; Yield: 70%

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, 1-(4-Bromophenyl)-2-phenyl-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Wuhan Shang Sai Optoelectric Technology Co., Ltd.; Wang Lei; Pan Biao; Wang Bo; Mu Guangyuan; (19 pag.)CN104370964; (2017); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 3543-74-6, name is Ethyl 4-(5-(bis(2-hydroxyethyl)amino)-1-methyl-1H-benzo[d]imidazol-2-yl)butanoate, 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 3543-74-6, Product Details of 3543-74-6

Example-2 Preparation of Ethyl 4-{5-[bis(2-chloroethyl)amino]-1-methyl-1H-benzimidazol-2-yl}butanoate (IV) 4-{5-[bis(2-hydroxyethyl)amino]-1-methyl-1H-benzimidazol-2-yl}butanoate (III, 90.0 g, 1.15 mole) was added to dichloromethane (6.24 L) and agitated till clear solution is formed. A solution of thionyl chloride (292.3 g, 2.52 mol) in dichloromethane (1.56 L) was added slowly in 2 to 3 hours. After complete addition of thionyl chloride solution, reaction mixture was refluxed at 35-45 C. for 6 hours. The reaction mixture was cooled to 20-30 C. and 1.95 L dichloromethane was added. Potassium carbonate solution (351.0 g in 1.95 L water) was added to the reaction mixture slowly to control the evaluation of effervescence. The layers were separated. The organic (dichloromethane) layer was washed with brine solution. The organic layer was concentrated at 30-35 C. under vacuum till viscous mass is obtained. The viscous mass was dissolved in acetone (1.95 L) and DM water (1.365 L) was slowly. The resulting mixture was stirred at 20-30 C. for one hour followed by cooling to 0-5 C. The solid separated out was washed with chilled mixture of acetone (390 mL) and DM water (195.5 mL) twice. The material was sucked dried to dryness and used as such for next step.

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, Ethyl 4-(5-(bis(2-hydroxyethyl)amino)-1-methyl-1H-benzo[d]imidazol-2-yl)butanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FRESENIUS KABI ONCOLOGY LIMITED; MISHRA, Bhuwan Bhaskar; KACHHADIA, Nikunj Shambhubhai; TOMAR, Vinod Singh; LAHIRI, Saswata; US2014/121383; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 103057-10-9, 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 103057-10-9 as follows.

EXAMPLE 1 STR49 To a solution of diisopropylamine (1.078 mL) in anhydrous THF (7 mL) was added n-butyllithium (3.08 mL; 2.5M) dropwise at 0 C. The resulting solution was stirred at 0 C. for 40 minutes and then was cooled to -23 C. To this mixture was added N-methyl-2-piperidinone (0.80 mL) (1), the mixture was stirred at -23 C. for 0.5 hour, and then at -78 C. for 1 hour. To the above mixture was added dropwise a solution of 4-chloromethyl-N-trityl-imidazole (2.70 g) STR50 in anhydrous THF (14 mL). The mixture was stirred at -78 C. for 4 hours and then was allowed to warm up to room temperature slowly overnight (16 hours). Water and ethyl acetate were added to the mixture, the resulting mixture was shaken vigorously, the layers separated, and the aqueous layer was extracted with ethyl acetate several times. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated to give the crude product, which was purified by flash chromatography (1% to 2% of ammonia saturated methanol in CH2 Cl2) to give 2 (1.58 g; 52% yield).

According to the analysis of related databases, 103057-10-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Schering Corporation; US5932596; (1999); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 1003-91-4, name is 2,4,5-Tribromo-1-methylimidazole, 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 1003-91-4, COA of Formula: C4H3Br3N2

To a solution of N-methylimidazole (1.64 g, 19.97 mmol) and sodium acetate (25 g, 300 mmol) in acetic acid (180 mL) at room temperature was added bromine (9.6 g, 60.07 mmol) dropwise as a solution in 20 mL acetic acid. The resulting mixture was stirred for 2.5 h at room temperature. Acetic acid was removed in vacuo, the residue was suspended in 500 mL water and stirred at room temperature for 10 minutes. The resultant precipitate was filtered, washed with water and dried under high vacuum to give 2,4,5-tribromo-l-methyl- lH-imidazole (1.82 g, 29% – some product remained in the mother liquor) as a light yellow powder. Used without further characterization. To a suspension of the tribromide (1.82 g, 5.71 mmol) in 45 mL water was added sodium sulfite (13 g, 103 mmol) and the resulting mixture was stirred at rapid reflux for 24 h. After cooling to room temperature, organics were extracted with ether (3 chi 75 mL), dried over magnesium sulfate, filtered and concentrated to give 1.61 g of a mixture of tri-, di- and monobromoimidazoles. This mixture was re-subjected to the reduction conditions (same quantity of sodium sulfite) using 15 mL of 3: 1 water/acetic acid as solvent and heating in a sealed vessel at 130 C for 60 h. After cooling to room temperature, the pH of the reaction mixture was adjusted to 9-10 by addition of 2 N sodium hydroxide. Organics were extracted with ether (3 chi 50 mL), dried over magnesium sulfate, filtered and concentrated to give crude 4-bromo-l -methyl- lH-imidazole (571 mg, ca. 62%). Used without further characterization.. 4-Butyl-l -methyl- lH-imidazole (95 mg, 22 %) was synthesized as in Example 3.1 using 4-bromo-l -methyl- lH-imidazole (571 mg, ca. 3.53 mmol) in place of 5-bromo-2- formylfuran and propylboronic acid (372 mg, 4.24 mmol) in place of hexylboronic acid. Used without further characterization. To a solution of diisopropylamine (0.13 mL, 0.918 mmol) in 2 mL anhydrous tetrahydrofuran at – 0C was added -butyllithium (0.34 mL, 2.5 M in hexanes) dropwise. The solution was stirred while warming to -20 C over 20 minutes. After cooling to -78 C, 4-butyl-l -methyl- lH-imidazole (95 mg, 0.765 mmol) was added dropwise as a solution in 2 mL anhydrous tetrahydrofuran. The resulting solution was stirred for 40 minutes at -78 C. Dimethylformamide (0.24 mL, 3.06 mmol) was added and the solution stirred while warming to room temperature. The reaction mixture was poured into 15 mL of 1 N hydrochloric acid and stirred for 5 minutes. The pH of the reaction mixture was adjusted to 7-8 by careful addition of saturated sodium bicarbonate solution. Organics were extracted with dichloromethane (3 chi 20 mL), dried over magnesium sulfate, filtered and concentrated. The crude residue was subjected to chromatography on silica gel with gradient elution (5-50% ethyl acetate in hexanes) to give l -methyl-4-propyl-lH-imidazole-2-carbaldehyde (9 mg, 8%) as an off-white solid. Used without further characterization.

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, 2,4,5-Tribromo-1-methylimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY; PROVID PHARMACEUTICALS INC.; EBRIGHT, Richard H.; EBRIGHT, Yon W.; SHEN, Juan; BACCI, James; HIEBEL, Anne-Cecile; SOLVIBILE, William; SELF, Christopher; OLSON, Gary; WO2013/192352; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 195053-92-0, The chemical industry reduces the impact on the environment during synthesis 195053-92-0, name is 2-(1-Trityl-1H-imidazol-4-yl)ethanamine, I believe this compound will play a more active role in future production and life.

A mixture of Meldrum’s acid (5.52 g, 38.3 mmol), potassium carbonate (26.5 g, 191 mmol) and methyl iodide (7.15 mL, 115 mmol) in acetonitrile (75 mL) was heated at 75 C in a sealed tube for 7 hrs. The mixture was cooled to room temperature, diluted with dichloromethane (300 mL), filtered and the filtrate evaporated to dryness in vacuo. Ethyl acetate (75 mL), hexanes (75 mL) and water (50 mL) were added and phases were separated. The organic layer was washed with 10% aqueous solution of sodium thiosulfate (50 mL) and water (50 mL); dried over anhydrous magnesium sulfate and solvent removed in vacuo to give 2,2,5,5-tetramethyl-[1,3]dioxane-4,6-dione as white solid. Yield: 6.59 g (79%). RF (SiO2, chloroform/ethyl acetate, 98:2): 0.60. 1H NMR spectrum (300 MHz, CDCl3, deltaH): 1.76 (s, 6 H); 1.65 (s, 6 H). A solution of 2-(1-Trityl-1H-imidazol-4-yl)-ethyl amine (5.00 g, 14.2 mmol) prepared as described above and triethylamine (9.86 mL, 70.7 mmol) in toluene (80 mL) was added dropwise over 50 min to a solution of the above dione compound (3.65 g, 21.2 mmol) in toluene (40 mL) at 75 C. The mixture was stirred at this temperature for additional 3 hrs (until the starting amine was detected on TLC), then it was evaporated to dryness. The residue was redissolved in chloroform (300 mL) and washed with 10% aqueous solution of citric acid (200 mL). The aqueous phase was extracted with chloroform (2 x 60 mL); the chloroform phases were combined, dried over anhydrous magnesium sulfate and solvent removed in vacuo. The residue was triturated with hot chloroform (140 mL); hexanes (70 mL) were added and the suspension was stirred at room temperature overnight. Solids were filtered off, washed with chloroform/hexanes mixture (1:1, 2 x 50 mL) and dried in vacuo to give the title product. Yield: 6.73 g (88%). M.p.: 161-162 C. RF (SiO2, chloroform/methanol, 85:15): 0.40. 1H NMR spectrum (300 MHz, DMSO-d6, deltaH): 12.45 (bs, 1 H); 7.66 (t, J=5.1 Hz, 1 H); 7.57-7.31 (m, 9 H); 7.26 (s, 1 H); 7.20-7.02 (m, 6 H); 6.66 (s, 1 H); 3.25 (m, 2 H); 2.57 (t, J=7.3 Hz, 2 H); 1.21 (s, 6 H).

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-(1-Trityl-1H-imidazol-4-yl)ethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Novo Nordisk A/S; SAUERBERG, Per; LAU, Jesper; LINDEROTH, Lars; KODRA, Janos Tibor; SPETZLER, Jane; GARIBAY, Patrick William; (119 pag.)EP3000482; (2016); 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. 1003-91-4, name is 2,4,5-Tribromo-1-methylimidazole, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 1003-91-4

To a solution of Example 69b (84 g, 263.3 mmol) in dry THF (2L) was added EtMgBr (88 mL, 263.3 mmol, 3.0M in ether) slowly under N2.The reaction was stirred at r.t. for 2 hours. Then about 2.0L water was added and filtered concentrated and the residue was extracted with EtOAc (50 mL * 2). The combined organic phase was washed with brine, dried over Na2S04, filtrated and concentrated under reduced pressure to give the crude product which was further purified by silica gel chromatography to give the pure product Example 69d (14.0 g) as white solid ‘HNMR (400 MHz, Chloroform- ) delta 7.48 (s, 1H), 3.63 (s, 3H). Example 69c (14.0g) as white solid. NMR (400 MHz, Chloroform- ) delta 6.94 (s, 1H), 3.60 (s, 3H). A solution of Example 69c&d (2.4 g, 10.0 mol) in ether (100 mL) was cooled to -78 C. under nitrogen atmosphere and then a 2.5 M n-BuLi solution in hexane (4.0 mL, 10.0 mol) added dropwise over 15 mins. The mixture was stirred at -78 C. for 30min and then DMF (2.0 mL) was added dropwise over 15 min. The mixture was stirred at -78 C. for 30min and quenched with saturated IN HQ (50 mL) at -78 C. The residue was extracted with EtOAc (50 mL * 2). The combined organic phase was washed with brine, dried over Na2S04, filtrated and concentrated under reduced pressure to give the crude product which was further purified by silica gel chromatography to give the pure product Example 69e (1.8 g, yield 95%) as yellow solid. NMR (400 MHz, Chloroform-d) delta 9.77 (d, J = 0.9 Hz, 1H), 7.51 (s, 1H), 3.93 (s, 3H).

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 1003-91-4.

Reference:
Patent; FRONTHERA U.S. PHARMACEUTICALS LLC; JIN, Bohan; DONG, Qing; HUNG, Gene; (212 pag.)WO2017/218960; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 1219741-21-5,Some common heterocyclic compound, 1219741-21-5, name is 5-Chloro-6-iodo-1H-benzo[d]imidazole-2(3H)-thione, molecular formula is C7H4ClIN2S, 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.

K2C03 (0.22 g, 1.61 mmol), followed by iodomethane (0.1 mL, 1.61 mmol), was added to a solution of 5-chloro-6-iodo- 1,3- dihydro-2H-benzimidazole-2-thione (1 g, 3.22 mmol) in acetone (20 mL) at 0C. The reaction was stirred at rt for 1 h. Additional K2C03 (1. 1 mmol) and iodomethane (1. 1 mmol) were added. The reaction was stirred at rt overnight, then the volatiles were removed and the residue was partitioned between EtOAc and water. Concentration of the EtOAc layer afforded the desired product as a white foam, which was used in the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Chloro-6-iodo-1H-benzo[d]imidazole-2(3H)-thione, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; JIANG, Jinlong; KASSICK, Andrew, J.; KEKEC, Ahmet; SEBHAT, Iyassu, K.; WO2011/106273; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem