Tag: M.W=100-200

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

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

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

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

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

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

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

Reference of 39070-14-9, 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 39070-14-9 as follows.

A mixture of 2-(1-methyl-5-nitro-1H-imidazol-2-yl)-ethanol (1.32 mmol) and 1-fluoro- 3 -nitrobenzene (1.67 mmol) and K2C03(465 mg, 3.36 mmol) in DMF (5 mL) was stirred 2 hours at ambient temperature followed by heating. The reaction was worked-up by extraction. The residue was purified by prep-HPLC with the following condition: column: XBridge preparative CI 8 OBD column 19x 150 mm, 5 um; mobile phase A: water (10 mmol/L NH4HCO3), mobile phase B: ACN; flow rate: 20 mL/min; gradient elution. The product-containing fractions were collected and then lyophilized to give l-methyl-5-nitro-2-(3-nitro-phenoxymethyl)-lH- imidazole. LC-MS: (ES, m/z) 279.07 (M+H)+; analysis: C, 47.53; H, 3.69; N, 20.24; O, 28.85.

According to the analysis of related databases, 39070-14-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENCIA CORPORATION; KHAN, Shaharyar; (80 pag.)WO2018/129258; (2018); 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. 705-09-9, name is 2-(Difluoromethyl)-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-(Difluoromethyl)-1H-benzo[d]imidazole

Preparation Example 1 To a solution of 4,6-dichloro-2-(methylsulfanyl)pyrimidine (5 g) in N,N-dimethylformamide (50 mL) were added potassium carbonate (5.3 g) and 2-(difluoromethyl)-1H-benzimidazole (3.9 g), and the mixture was stirred at room temperature for 5 hours. To the reaction mixture was added water, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and then the residue was purified by silica gel column chromatography (hexane:ethyl acetate) to obtain 1-[6-chloro-2-(methylsulfanyl)pyrimidin-4-yl]-2-(difluoromethyl)-1H-benzimidazole (5.49 g) as a white powder.

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; Astellas Pharma Inc.; TAKAHASHI, Fumie; IMADA, Sunao; ASANO, Toru; KOZUKI, Yoshihiro; MAEDA, Junko; KATO, Koji; FUKAHORI, Hidehiko; SHIWAKU, Masahiko; US2013/150364; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol, 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 1615-14-1, HPLC of Formula: C5H8N2O

Example 10: 2-Imidazol-l-ylethyl 4-[(4-methoxyphenyl)amino]-6-(methylcarbamoyl)- quinoIine-3-carboxyIate. To a suspension of 4-[(4-methoxyphenyl)amino]-6-(methylcarbamoyl)-quinoline-3- carboxylic acid (1.0 g, 2.8 mmol) in dry tetrahydrofuran (15 mL) at 0 0C under nitrogen atmosphere was added l-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (2.0 g, 11.2 mmol), hydroxybenzotriazole (HOBt, 0.64 g, 4.84 mmol), triethylamine (3.2 mL, 2.3 mmol) and 2-hydroxyethylimidazole (0.65 g, 3.4 mmol). The reaction mixture was slowly brought to room temperature and stirred for 12 hours. The reaction mixture was concentrated in vacuo and after aqueous work up, extracted with dichloromethane, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified on column (flash chromatography on alumina gel, chloroform/methanol 99.8 : 0.2) to give 0.25 g (23 % yield) of 2-imidazol-l-ylethyl 4-[(4-methoxyphenyl)amino]-6-(methylcarbamoyl)quinoline-3-carboxylate as a pale yellow solid. LC-MS (m/z) 446.2 (M+l). 1H NMR delta (CDCl3) 10.65 (s, IH), 9.16 (s, IH), 8.05 (dd, IH, J1 = 8.7 Hz, J2 = 1.8 Hz), 7.97 (d, IH, J= 8.7 Hz), 7.84 (s, IH), 7.76 (s, IH), 7.22-7.10 (m, 3H), 7.08 (s, IH), 6.97 (d, 2H, J= 9.0 Hz), 5.67 (broad s, IH), 4.75 – 4.60 (m, 2H), 4.50-4.35 (m, 2H), 3.87 (s, 3H), 2.88 (s, 3H).

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-(1H-Imidazol-1-yl)ethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CLANOTECH AB; MALM, Johan; RINGOM, Rune; CALDIROLA, Patrizia; WESTMAN, Jacob; WO2010/133669; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem