Month: September 2021

Related Products of 616-47-7, These common heterocyclic compound, 616-47-7, name is 1-Methyl-1H-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.

1-methylimidazole (1 mmol, 82.1 mg),Carbon tetrabromide (1.1 mmol, 364.8 mg) was placed in a 10 mL round bottom flask.Added 5 mL of N,N-dimethylformamide and sodium tert-butoxide (4.0 mmol, 384.4 mg).Stir at room temperature for 3 hours,TLC monitored the endpoint of the reaction. The mixture is poured into water and extracted with dichloromethane. The organic phase is collected, dried, and the dichloromethane is removed by rotary evaporation.Crude product. The crude product was subjected to silica gel column chromatography with petroleum ether and ethyl acetate as eluents (volume ratio = 10:1) to obtain 2-Bromo-1-methylimidazole (red-brown liquid, 101.4 mg, yield 63%).

The synthetic route of 616-47-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Liaoning University; Liang Fushun; Liu Xia; Han Zhengbo; Su Zhongmin; (10 pag.)CN107501023; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 6160-65-2, 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. 6160-65-2, name is 1,1′-Thiocarbonyldiimidazole, This compound has unique chemical properties. The synthetic route is as follows.

After performing this reaction several times, all product fractions were pooled and the resulting residue of the dihydroxyl derivative (124 mg, 269 mumol, 1 eq.) was dissolved under argon in tetrahydrofurane (80 mL) in a 250 mL flame-dried flask. To this solution was added thiocarbonyl diimidazole (480 mg, 2.69 mmol, 10 eq.) and 4-(dimethylamino)pyridine (329 mg, 2.69 mmol, 10 eq.). The resulting reaction mixture was heated to 80C and stirred at this temperature overnight. After cooling to room temperature, a small portion of silica gel was added and the solvent was removed under reduced pressure. The adsorbed crude product was purified by flash column chromatography (50% ethyl acetate in cyclohexane) to yield 119 mg (237 mumol, 88%) of (VII) as a colorless solid.

The chemical industry reduces the impact on the environment during synthesis 1,1′-Thiocarbonyldiimidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Max-Planck-Gesellschaft zur Foerderung der Wissenschaften e.V.; EP2210881; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 57090-88-7, name is 1H-Imidazole-4-carbonitrile, 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 57090-88-7, name: 1H-Imidazole-4-carbonitrile

Example 1 Production of 1-(1H-imidazol-4-yl)-2-methyl-1-propanone A solution of 4-cyanoimidazole (42.7 g, 0.458 mol) in THF (500 ml) was added dropwise over 30 min to a solution (1.4 L, 1.47 mol, 3.2 equivalents) of 1.1 M isopropyl magnesium bromide in THF at 0 to 10°C under a nitrogen atmosphere. The mixture was stirred at 15 to 25°C for 3 h. Water (430 ml) and 10percent aqueous sulfuric acid solution (860 ml) were successively added dropwise, and the mixture was stirred at 30 min. A 30percent aqueous sodium hydroxide solution was added dropwise to adjust the pH to 8. After partitioning, the aqueous layer was extracted with ethyl acetate (300 ml * 2). The organic layer was combined, and the mixture was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine, and concentrated under reduced pressure. The concentration residue was broken up with isopropyl ether (300 ml). The crystals were collected by filtration and washed with isopropyl ether. The crystals were dried in vacuo (40°C) to give 1-(1H-imidazol-4-yl)-2-methyl-1-propanone (51.9 g, yield 82percent). 1H-NMR (CDCl3): delta1.25(6H, d, J=6.9Hz), 3.36(1H, quint, J=6.9Hz), 7.81(1H, s), 7.87(1H, s)

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, 1H-Imidazole-4-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1193258; (2002); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde, molecular formula is C5H6N2O, 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. Recommanded Product: 39021-62-0

To a cloudy mixture of 6-bromo-2,4-dichloro-3-phenylquinoline (290.5 mg, 0.823 mmol, Intermediate 1: step c) and 1-methyl-1H-imidazole-5-carbaldehyde (90.6 mg, 0.823 mmol) in THF (8 mL) under nitrogen at -78 C. was added n-BuLi (1.6 M in hexane, 0.643 mL, 1.03 mmol) dropwise. The resulting solution was stirred at -78 C. for 3 hours, then was warmed to 0 C. for 15 minutes before addition of saturated aqueous NH4Cl to quench. The mixture was diluted with water and was extracted three times with EtOAc. The organic phase was dried (Na2SO4), filtered, and concentrated. The residue was purified by flash column chromatography (silica gel, 0-6% MeOH-DCM) to afford the title compound as a white powder.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 39021-62-0, its application will become more common.

Reference:
Patent; Janssen Pharmaceutica NV; Leonard, Kristi A.; Barbay, Kent; Edwards, James P.; Kreutter, Kevin D.; Kummer, David A.; Maharoof, Umar; Nishimura, Rachel; Urbanski, Maud; Venkatesan, Hariharan; Wang, Aihua; Wolin, Ronald L.; Woods, Craig R.; Fourie, Anne; Xue, Xiaohua; Cummings, Maxwell D.; (53 pag.)US2017/258782; (2017); 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 496-46-8 as follows. Recommanded Product: 496-46-8

Preparation tetranitro glycoluril: equipped with a reflux condenser, a thermometer, a stirrer, pressure-equalizing dropping funnel, the reaction 3000ml four-necked round flask, 500ml of fuming nitric acid.When the temperature to about 10 , 20g glycoluril added rapidly, stirred to dissolution, to give glycoluril – fuming nitric acid solution; the glycoluril – nitric acid solution is sent down to the temperature of the smoke 0 ~ 5 , 250ml of acetic anhydride was added dropwise, drops added maintaining the temperature at 0 ~ 5 ; acetic anhydride addition was completed, the nitration temperature is maintained at 0 ~ 5 , nitration reaction after 4h, the temperature raised to nitration 5 ~ 10 , 3H continued nitration; nitrated using a temperature gradient to gradually warm ,, 5 gradient for 2 hours and then raised 5 , nitration began maintaining the temperature at 0 deg.] C, nitration reaction 2h, 5 increased, i.e., the temperature was raised 5 nitration, nitration continued 2h, then increased 5 , i.e. nitration temperature was raised to 10 , maintained for 3 hours.10min nitration reaction bottle with a precipitate beginning, gradually warming nitration temperature gradient, the amount of precipitation as the reaction temperature, the reaction time increased, the precipitation was complete, the reaction mixture was lowered vial -10 ~ 0 , the reaction was stopped, the bottle within fritted funnel mixture was filtered, the white solid was washed with tetranitromethane glycoluril dichloromethane to large neutral stand soaked in dichloromethane

According to the analysis of related databases, 496-46-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hubei Aerospace Institute of Chemical Technology, CASC; Ha, HengXin; (8 pag.)CN105777575; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 7152-24-1,Some common heterocyclic compound, 7152-24-1, name is 2-(Methylthio)benzimidazole, molecular formula is C8H8N2S, 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.

EXAMPLES Synthesis of Compound 1 A suspension of 164 g (1.0 mol) of 2-methylthiobenzimidazole (manufactured by Tokyo Kasei Co. or Aldrich Co.) in 1500 ml of water was prepared. To it were added 1.65 g (0.005 mol) of sodium tungstate dihydrate and 280 ml of 35% aqueous hydrogen peroxide. The mixture was placed in a water bath of 50 C. and stirred for 6 hours. During this period, 181 g of 2-methanesulfonylbenzimidazole precipitated and was collected by filtration.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(Methylthio)benzimidazole, its application will become more common.

Reference:
Patent; Fuji Photo Film Co., Ltd.; US5097042; (1992); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 16681-59-7, name is 2-Bromo-1-methyl-1H-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. COA of Formula: C4H5BrN2

The 3-methyl-1-(1-methyl-1 H-imidazol-2-yl)-2-oxo-4-imidazolidinecarboxylic acid used in the method described above was prepared as follows: (i) To a stirred solution of 1 ,1-dimethylethyl 3-methyl-2-oxo-4- imidazolidinecarboxylate (0.200 g, 1.00 mmol) (prepared as described in step (iii) of Example 13, starting from (4S)-2-oxo-3-{[(phenylmethyl)oxy]carbonyl}-4- imidazolidinecarboxylic acid) and 2-bromo-1-methyl-1 H-imidazole (0.146 ml, 1.500 mmol) in 1 ,4-dioxane (8 ml) was added potassium phosphate (1.062 g, 5.00 mmol), copper(l) iodide (0.190 g, 1.000 mmol) and trans-N,N-dimethylcyclohexane-1 ,2- diamine (0.155 ml, 1.000 mmol) and the mixture heated at reflux under argon overnight. The mixture was cooled to room temperature and diluted with dichloromethane. The solid was filtered off, washed with dichloromethane and the filtrate reduced under vacuum. The residue was re-dissolved in dichloromethane and washed with 0.880 ammonia solution (x2), water then brine and passed through a hydrophobic frit and the organic layer reduced under vacuum. The residue was purified by Flashmaster automated silica gel chromatography eluting with 0-10% methanol in dichloromethane to give 1 ,1-dimethylethyl 3-methyl-1-(1-methyl-1 H- imidazol-2-yl)-2-oxo-4-imidazolidinecarboxylate (145 mg, 37.8 % yield). LC/MS[M+H]+ = 281.

The synthetic route of 2-Bromo-1-methyl-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/119825; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 15965-31-8, name is 5-Chloro-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: imidazoles-derivatives

A stirred suspension of 4-chloro-lH-imidazole (9.75 mmol, 1.0 g) , 2-chloro-5-nitropyridine (9.75 mmol, 1.54 g) and potassium carbonate (11.70 mmol, 1.61 g) in DMF (10 mL) was heated at 80 C for 3 hours. The mixture was cooled to room temperature and water was added. The resulting precipitate was filtered, washed with water and dried to give crude 6- ( 4-chloroimidazol-l-yl ) -3- nitropyridine (1.94 g, 89%).

The synthetic route of 15965-31-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ONO PHARMACEUTICAL CO., LTD.; SAITO, Tetsuji; HIGASHINO, Masato; KAWAHARADA, Soichi; LEWIS, Arwel; CHAMBERS, Mark Stuart; RAE, Alastair; HIRST, Kim Louise; HARTLEY, Charles David; WO2015/115673; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 16042-25-4,Some common heterocyclic compound, 16042-25-4, name is 2-Imidazolecarboxylic acid, molecular formula is C4H4N2O2, 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.

To a suspension of 0.351 g of imidazole-2-carboxylic acid (3.13 mmol) in 15 ml DMF were added 0.508 g of CDI (3.13 mmol) and 0.43 ml triethylamine (3.13 mmol), and the mixture stirred at ambient temperature for 1 h. Then the mixture was refluxed for 30 min. After cooling to ambient temperature, 0.5 g of 2-methoxy-5-(tetrahydro-pyran-4-yl)-phenylamine (2.4 mmol) was added and the reaction mixture was heated to reflux for 16 h. The mixture was evaporated and the residue taken up in water (40 ml) and extracted 3 times with methylene chloride. The combined organic phases were tried on sodium carbonate, evaporated and the residue was stirred in hot ethyl acetate. After filtration and trying 0.42 g 1H-Imidazole-2-carboxylic acid [2-methoxy-5-(tetrahydro-pyran-4-yl)-phenyl]-amide (57%) were obtained as a yellow solid; M.p.: 227-228 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Imidazolecarboxylic acid, its application will become more common.

Reference:
Patent; Flohr, Alexander; Jakob-Roetne, Roland; Norcross, Roger David; Riemer, Claus; US2004/229862; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 57667-50-2, 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. 57667-50-2, name is 1-Propyl-1H-benzo[d]imidazol-2-amine, This compound has unique chemical properties. The synthetic route is as follows.

1 ,3-bis(1 -Propyl-1 H-benzo[d]imidazol-2-yl)urea (1 9a) and 1 0-propyl-3-(1 -propyl-1 H-benzo[d]-imidazol2-yl)benzo[4,5]imidazo[1,2-a][1,3,5]triazine-2,4(3H,1OH)-dione (9b) were obtained in 8% (16.0 mg,0.045 mmol) and 12% (0.027 g, 0.067 mmol) yield respectively via a reaction of 1-propyl-1H- benzo[d]imidazol-2-amine (20a) (0.200 g, 1.141 mmol), 4-nitrophenylchloroformate (0.127 g, 0.628 mmol) and DIPEA (0.258 mL, 1.484 mmol) in CH2CI2 (4.0 mL) at room temperature. Reaction time 16h. 1,3-bis(1-Propyl-1H-benzo[d]imidazol-2-yl)urea (19a) White solid ; m.p. 178 o 1H-NMR (400 MHz, CDCI3): : 7.30-7.29(m, 2H), 7.13-7.09(m, 6H), 4.02(t, 4H, J= 7.20 Hz), 1.78(d, 4H, J= 7.60 Hz),0.88 (t, 6H, J = 7.60 Hz). 1 0-propyl-3-(1 -propyl-1 H-benzo[d]imidazol-2-yl)benzo[4,5]imidazo[1 2- a][1 ,3,5]triazine-2,4(3H,1OH)-dione (9b). Colorless solid; m.p. 222 C. 1H-NMR (400 MHz, DMSO-d6):: 8.01 (d, 1H, J = 7.60 Hz), 7.75 (d, 1H, J = 8.00 Hz), 7.71 -7.67 (m, 2H), 7.54-7.49 (t, 2H, J = 8.00 Hz), 7.41-7.28(m, 3H), 4.21-4.04(m, 4H), 1.91-1.81 (m, 2H), 1.79-1.69(m, 2H), 1.00(t, 3H, J= 7.20 Hz), 0.87 (t, 3H, J = 7.20 Hz).

The chemical industry reduces the impact on the environment during synthesis 1-Propyl-1H-benzo[d]imidazol-2-amine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; UNIVERSITEIT ANTWERPEN; MAES, Bert; WYBON, Clarence; CHEN, Chen; BHEETER, Charles Beromeo; SERGUEEV, Serguei; (88 pag.)WO2017/46133; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem