Author: Jessica.F

Adding a certain compound to certain chemical reactions, such as: 288-32-4, name is 1H-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 288-32-4, Quality Control of 1H-Imidazole

To a stirred solution of imidazole (6.80 g, 100 mmol) in anhydrous dichloromethane (500 mL) was added BrCN (3.70 g, 33 mmol) and stirring was continued at reflux for 30 min. The mixture was cooled to room temperature and concentrated to afford di(imidazole-1-yl)methanimine (4.05 g, 72 %) as a pale yellow solid which was used without further purification.H NMR (DMSO-d6): 10.21 (br s, 1 H, NH), 8.09 (s, 2 H, 2 * CH), 7.57 (s, 2 H, 2 * CH), 7.12 (s, 2 H, 2 * CH).

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, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SHIRE, LLC; FRANKLIN, Richard; TYSON, Robert G; GOLDING, Bernard T; WO2012/85586; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 5098-11-3, name is 5-Amino-1H-imidazole-4-carbonitrile, 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. Formula: C4H4N4

Example 1 : General procedure for the preparation of cyano-imidazo[1 ,5- a]pyrimidines of general formula (I) following Scheme 1N-[3-(8-cyano-imidazo[1 ,5-a]pyrimidin-4-yl)-phenyl]-N-ethyl- ethanesulfonamide0.035 g (0.32 mmol) of delta-amino-I H-imidazole^-carbonitrile and 0.1 g (0.32 mmol) of N-[3-[3-(dimethylamino)-1 -oxo-2-propenyl]phenyl]-N-ethyl- ethanesulfonamide were dissolved in 10 ml of glacial acetic acid. After refluxing for 4 hours, the solvent was removed by reduced pressure distillation. To the resultant residue 10 ml of dichloromethane and 10 ml of a saturated solution of sodium bicarbonate were added. The two layers were separated, and the aqueous layer was washed with 10 ml of dichloromethane. The organic layers were washed with 10 ml of water and dried over magnesium sulfate. The dichloromethane layer was evaporated to dryness to yield an oil which, in the presence of ethyl acetate gave a yellow solid, 58 mg (yield 51%) of N-[3-(8-cyano-imidazo[1 ,5-a]pyrimidin-4-yl)-phenyl]-N-ethyl- ethanesulfonamide1H NMR (400 MHz, CDCI3): delta 1.2 (3H, t, J= 7.2 Hz), 1.41 (3H, t, J= 7.6 Hz), 3.08 (2H, q, J= 7.6 Hz), 3.84 (2H, q, J= 7.6 Hz), 6.85 (1 H, d, J= 4 Hz), 7.58- 7.71 (3H, m), 7.76-7.77 (1 H, m), 8.25 (1 H, s), 8.56 (1 H, d, J= 4 Hz). MS (ES) m/z = 356 (MH+) HPLC = 94.2%

The synthetic route of 5-Amino-1H-imidazole-4-carbonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FERRER INTERNACIONAL, S. A.; WO2006/84835; (2006); 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. 5465-29-2, name is 2-Propylbenzimidazole, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Propylbenzimidazole

The 1H-benzo[d]imidazole 5a(2.50 mmol) was dissolved in 10 ml of abs. DMF. Sodium hydride(60% dispersion in mineral oil) (0.2 g, 5 mmol) was added withcooling. After the gas formation stopped, 40-bromomethyl-[1,10-biphenyl]-2-carbonitrile dissolved in 2 ml of abs. DMF was addeddropwise and the solutionwas stirred for 1 h under cooling in an icebath and further 2 h at RT. Water was added and after the solutionwas acidified with HCl, the product was extracted three times withmethylene chloride. The combined organic layers were dried overNa2SO4 and evaporated to dryness in vacuo. The crude product waspurified by column chromatography on silica gel with methylenechloride/methanol (95:5) and recrystallized from diethyl ether/methanol.

The synthetic route of 5465-29-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Obermoser, Victoria; Urban, Margarethe E.; Murgueitio, Manuela S.; Wolber, Gerhard; Kintscher, Ulrich; Gust, Ronald; European Journal of Medicinal Chemistry; vol. 124; (2016); p. 138 – 152;,
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. 71759-87-0, name is 4-Iodo-1-methyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C4H5IN2

To a solution of chloride 2 (scheme 1) (2.45 g, 14.4 mmol) in THF (48 mL) at -78C was slowly added w-BuLi (2.5M in hexane, 7.2 mL, 18.0 mmol). The reaction mixturewas stirred for one hour [at -78C] followed by slow addition of ZnCl (0.5M in THF, 36mL, 18.0 mmol). In a few minutes the reaction mixture was allowed to warm to roomtemperature and stirred for one hour.[0422] A solution of 4-iodo-l -methyl- 1/f-imidazole (1.50 g, 7.2 mmol) Tet. Lett. 2004.45. 5529] in THF (5 mL) and the tetrakis(triphenylphosphine) palladium (0) (0.83 g, 0.72mmol) were added to the reaction mixture which was heated to reflux for 1 hour, cooled toroom temperature, diluted with aqueous ammonium hydroxide and, finally neutralized witha IN HC1 solution. The acidic solution was extracted with DCM, the extract was washedwith water and brine, dried over anhydrous magnesium sulfate, filtered and evaporatedunder reduced pressure. The residue was purified by flash chromatography (eluents DCM,then DCM-MeOH, 97:3) to afford title compound 175 (1.45 g, 81% yield) as a yellow solid.LRMS (M+l) 263.9 (100%), 265.9 (33%).

According to the analysis of related databases, 71759-87-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; METHYLGENE, INC.; WO2006/10264; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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