Imidazoles-derivatives

3314-30-5, A common heterocyclic compound, 3314-30-5, name is 1H-Benzo[d]imidazole-2-carbaldehyde, molecular formula is C8H6N2O, 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.

Typical procedure for the preparation of Benzimidazolyl-benzimidazole; A solution of benzimidazole-2-aldehyde 1 (0.5 mmol) and diamine 2 (0.5 mmol) in dimethylacetamide (4mL) was stirred at 100 0C for 12h. Solvent was evaporated and residue was purified by preparative HPLC to give benzimidazole derivative 3. 1H NMR (300 MHz, MeOH-doe : S 2.52 (s, 3H), 2.85 (brs, 4H)5 3.25 (brs, 4H)5 7.05-7.15 (m, 2 H), 7.25-7.35 (s overlapped with m, 2 H)5 7.60-7.75 (m, 4H); LCMS mlz 333 (M + H+), ELSD 99percent.

The synthetic route of 3314-30-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHEMBRIDGE RESEARCH LABORATORIES, INC.; WO2007/56155; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

872-82-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 872-82-2 name is 2-(1H-Imidazol-5-yl)ethanol, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

4-lmidazoleacetic acid hydrochloride (5.93 g, 36.47 mmol) in methanol (125 mL) was saturated with HCI gas and stirred at room temperature for 5.5 h, then concentrated to give a quantitative yield of 4-imidazoleacetic acid methyl ester hydrochloride as a white solid which had NMR (MeOH- d4) delta 8.87 (d, J = 1.2 Hz, 1H), 7.46 (s, 1 H), 3.89 (s, 2H) 3.72 Patent; PFIZER PRODUCTS INC.; WO2007/34277; (2007); A1;,
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Imidazole | C3H4N2 – PubChem

The chemical industry reduces the impact on the environment during synthesis 26576-46-5, name is 5-Acetoacetlamino benzimdazolone, I believe this compound will play a more active role in future production and life. 26576-46-5

To 30 parts of dimethylacetamide were added 5.6 parts of 3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid,And 2.6 parts of thionyl chloride were added, and the mixture was stirred at 40 to 50 C. for 0.5 hour. 3 parts of 4′-aminoacetanilide was added, and the mixture was heated at 90 to 100 C. for 3 hours. 30 parts of water and 8.3 parts of concentrated hydrochloric acid were added, and the mixture was stirred at 90 to 100 C. for 1 hour.It was cooled to 0 to 10 C., and 1.4 parts of sodium nitrite was added to diazotize. 5 parts of sodium hydroxide and 4.7 parts of 5- (acetoacetamido) -2-benzimidazolinone were dissolved in 150 parts of water, the aforementioned diazo solution was added, and the mixture was stirred at 20 to 30 C. for 4 hours, then 70 to 80 0> C for 1 hour. After filtration, washing with water and drying, 11.6 parts of a yellow pigment additive (H) represented by the following formula (H) was obtained.

The chemical industry reduces the impact on the environment during synthesis 26576-46-5. I believe this compound will play a more active role in future production and life.

Reference:
Patent; DAINICHISEIKA COLOR & CHEMICALS MANUFACTURING COMPANY LIMITED; YANAGIMOTO, HIROMITSU; (36 pag.)JP2017/125083; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

98873-55-3, 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. 98873-55-3, name is 2-(1H-Imidazol-1-yl)acetonitrile, A new synthetic method of this compound is introduced below.

EXAMPLE 7 Synthesis of 2-(1-imidazolyl)-2-[4 (2-chlorophenyl)1,3-dithiolan-2-ylidene]acetonitrile (Compound Nos. 34 and 35) To a mixed solution of 2.2 g (0.02 mole) of 1cyanomethylimidazole, 1.60 g (0.02 mole) of carbon disulfide and 10 ml of dimethyl sulfoxide wa added 3.0 g (0.05 mole) of potassium hydroxide powder, and the reaction was carried out with stirring at room temperature for 1 hour. Then, 6.0 g (0.02 mole) of 2′-chloro-(1,2-dibromoethyl)benzene was added dropwise with stirring, and the resulting solution was subjected to reaction for another 2 hours. After completion of the reaction, 20 ml of water was added to the reaction solution, after which the resulting mixture was subjected to extraction with ethyl acetate, and the organic layer was washed with water and dried. The solvent was distilled off and the residue was purified by silia gel chromatography to obtain 0.3 g of the Z isomer and 1.3 g of the E isomer individually in the form of light-yellow crystals. The Z isomer: melting point 119.4 C., yield 5%. The E isomer: melting point 141.5 C., yield 20%.

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; Nihon Nohyaku Co., Ltd.; US4636519; (1987); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

152628-02-9, A common heterocyclic compound, 152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, molecular formula is C19H20N4, 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.

In a 500 mL four-necked flask equipped with a mechanical stirrer and a thermometer, 30.0 g (98.6 mmol) of 2-n-propyl-4-methyl-6- (1′-methylbenzimidazol-2-yl) benzimidazole, 124 g of methylpyrrolidone and 11.1 g (98.9 mmol) of potassium tert-butoxide were added and stirring was started. While cooling the 4-necked flask with ice water, a solution of 33.1 g (108.5 mmol) of 4′-bromomethylbiphenyl-2-carboxylic acid methyl ester in 124 g of N-methylpyrrolidone was heated at an internal temperatureWas added dropwise at 0 to 10 C. over 25 minutes.After the dropwise addition, the mixture was stirred at an internal temperature of 0 to 10 C. for 3 hours.The reaction solution was sampled and analyzed by HPLC. As a result, 2-n-propyl-4-methyl-6- (1′-methylbenzimidazol-2-yl) benzimidazole was not detected and 82.5%4 ‘- [[4-methyl-6- (1 -methyl- 1 H- benzimidazol-2-yl) -2-propyl- 1 H- benzimidazol- 1 – yl] methyl] biphenyl- there were.150 g of water and 130 g of toluene were placed in a 1000 mL four-necked flask equipped with a mechanical stirrer, and while stirring,A reaction solution of a 500 mL four-necked flask was added dropwise.30 g of 35% hydrochloric acid was added to acidify the aqueous layer, and the organic layer and the aqueous layer were separated.209 g of toluene and 46 g of 25% sodium hydroxide aqueous solution were added to the aqueous layer,The aqueous layer was made alkaline and separated into an organic layer and an aqueous layer.An aqueous layer and 78 g of toluene were put into a 500 mL separating funnel and extracted,It was separated into an organic layer and an aqueous layer.The organic layers were combined and concentrated,A solution of 4 ‘- [[4-methyl-6- (1 -methyl- 1 H- benzimidazol-2-yl) -2- propyl- 1 H- benzimidazol- 1 – yl] methyl] biphenyl- 63.3 g of crude product was obtained. This crude product contained about 13.5 g of toluene, and the content of the target product was 49.8 g (yield 95.6%).

The synthetic route of 152628-02-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DNP FINE CHEMICALS UTSUNOMIYA COMPANY LIMITED; MATSUMOTO, TAKAFUMI; IKEDA, SHIN; SUZUKI, YOSHINOBU; (12 pag.)JP5711888; (2015); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1003-21-0, Adding a certain compound to certain chemical reactions, such as: 1003-21-0, name is 5-Bromo-1-methyl-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 1003-21-0.

Intermediate 66: step b (1-methyl-1H-imidazol-5-yl)(pyrimidin-2-yl)methanone 5-Bromo-l-m.ethyl-lH-im.idazole (6.66 g, 41 ,4 mmol) was added to a round bottom flask followed by tetrahydrofuran (150 mL) under an N2atmosphere. The contents were cooled to 0 C in an ice water bath. EtMgBr (3.0 M solution in THF, 13.3 mL, 39.8 mmol) was added slowly via syringe over approximately 5 minutes, then the ice bath was removed and the contents allowed to warm and stirred at room temperature for approximately 30 minutes. The vessel was then re-cooled to 0 C and a solution of N-methoxy-N-methylpyrimidine-2-carboxamide (3.09 g, 15.9 mmol, Intermediate 66: step a) in THF (20 mL) was cannulated into the reaction vessel. The contents were allowed to stir at 0 C, then slowly warmed to room temperature, then heated to 40 C in an oil bath for approximately 36 hours. The contents were then cooled to 0 C, quenched with a saturated aqueous NH4CI solution, diluted with ethyl acetate and transferred to a separatory funnel. The aqueous layer was separated, extracted twice with EtOAc, then the combined organic phases were dried over MgS04, filtered, then distilled under reduced pressure to yield an amber oil. The crude product was purified by flash column chromatography (silica gel, 0-10% DCM / (10% of a 2 M N MeOH in DCM)) to provide the title compound.

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, 5-Bromo-1-methyl-1H-imidazole, other downstream synthetic routes, hurry up and to see.

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.; JONES, William Moore; GOLDBERG, Steven; WO2015/57205; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

7189-69-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 7189-69-7 name is 1,1′-Sulfonyldiimidazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: A solution of 500 mg (4.46 mmol) of 2-fluorophenol 1.769 g (8.92 mmol) of 1,1?-sulfonyldiimidazole in 15 mL of tetrahydrofuran was treated with 727 mg (2.23 mmol) of cesium carbonate. The reaction was stirred for 12 h, concentrated, and the residue was partitioned between the ethyl acetate and water (10 mL each). The organic layer was washed sequentially with saturated ammonium chloride solution and brine. After drying over the anhydrous sodium sulfate, the organic layer was concentrated and chromatographed on silica with 1:5 ethyl acetate / hexane as the eluant to afford 880 mg (90%) of 11bas a clear oil:

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,1′-Sulfonyldiimidazole, and friends who are interested can also refer to it.

Reference:
Article; Yang, Baocheng; Sun, Zhexun; Liu, Changzhi; Cui, Yan; Guo, Zhilei; Ren, Yuwei; Lu, Zhijian; Knapp, Spencer; Tetrahedron Letters; vol. 55; 49; (2014); p. 6658 – 6661;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

288-32-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 288-32-4 name is 1H-Imidazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: For the catalysis reaction, the catalyst C1 (12 mg,0.01 mmol), imidazole (1.0 mmol), aryl halide(1.0 mmol), NaOH (80 mg, 2.0 mmol), and dimethylsulfoxide (DMSO, 5 mL) were taken in a sealed tube. The reaction mixture was stirred at 100 C for 4 h and then cooled to room temperature. After adding 5 mL of H2O, the solution was extracted with ethyl acetate. The organic layer was then dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure.The N-arylated product was finally obtained by columnchromatography on silica gel.

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:
Article; Gou, Gao-Zhang; Wu, Na; Zhang, Ju-Cheng; Shi, Ling; Liu, Gui-Yang; Liu, Wei; Mang, Chao-Yong; Chi, Shao-Ming; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical; vol. 57A; 2; (2018); p. 181 – 185;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

71759-88-1, The chemical industry reduces the impact on the environment during synthesis 71759-88-1, name is 5-Iodo-1-methyl-1H-imidazole, I believe this compound will play a more active role in future production and life.

EXAMPLE 93B (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (4-cyanophenyl)(hydroxy)(1-methyl-1H-imidazol-5-yl)acetate A mixture of zinc dust (9.4 g, 143.7 mmol) in THF (5 mL) was treated with 1,2-dibromoethane (0.62 mL, 7.2 mmol), heated to 50 C., stirred for 15 minutes, and cooled to 30 C. The mixture was treated with chlorotrimethylsilane (0.91 mL, 7.2 mmol), stirred for 5 minutes, heated to reflux, treated slowly with 5-iodo-1-methyl-1H-imidazole (20.0 g, 96.2 mmol), and continued to reflux for 30 minutes. The reaction was cooled to room temperature and stirring was aborted to allow the excess zinc to settle to the bottom of the flask. A solution of magnesium bromide diethyl etherate (10.3 g, 39.9 mmol) and Example 93A (50.0 g, 79.8 mmol) in THF (100 mL) was cooled to -10 C. and treated with a solution of the 1-methyl-5-zinciodo-1H-imidazole from above in THF (120 mL) over 15 minutes. The mixture was warmed to room temperature, stirred for 18 hours, quenched with saturated NH4Cl (100 mL), and the layers were separated. The aqueous phase was extracted with ethyl acetate (300 mL) and the combined organic phases were washed with brine. The reaction mixture was filtered through diatomaceous earth (Celite), treated with toluene (250 mL), concentrated at a bath temperture of 60 C. The mixture was allowed to sit for 18 hours and then filtered. The filter cake was washed with toluene and dried under vacuum at 50 C. to provide 30.0 g (81% potent, 77% yield, 97.4% de). MS (ACPI) m/e 396 (M+H)+; 1H NMR (CD3OD) delta 8.02 (br s, 1H), 7.78 (d, 2H), 7.63 (d, 2H), 7.13 (br s, 1H), 4.76 (ddd, 1H), 3.49 (s, 3H), 2.06 (br d, 1H), 1.72-1.60 (m, 2H), 1.55-1.42 (m, 1H), 1.30 (m, 11), 1.14 (q, 1H), 1.07-0.98 (m, 2H), 0.95 (d, 3H), 0.94-0.84 (m, 1H), 0.66 (d, 3H), 0.50 (d, 3H).

The chemical industry reduces the impact on the environment during synthesis 5-Iodo-1-methyl-1H-imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Claiborne, Akiyo K.; Gwaltney, II, Stephen L.; Hasvold, Lisa A.; Li, Qun; Li, Tongmei; Lin, Nan-Horng; Mantei, Robert A.; Rockway, Todd W.; Sham, Hing L.; Sullivan, Gerard M.; Tong, Yunsong; Wang, Gary; Wang, Le; Wang, Xilu; Wang, Wei-Bo; US2002/115640; (2002); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

52099-72-6, 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. 52099-72-6, name is 1-(Prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one, A new synthetic method of this compound is introduced below.

1-Isopropyl-1,3-dihydro-benzoimidazol-2-one A mixture of 1-isopropenyl-1,3-dihydro-benzoimidazol-2-one (J. Davoll, J. Chem. Soc. 1960, 308) (6.90 g, 39.6 mmol) and 10% palladium on carbon (1.0 g) in MeOH (50 mL) was placed in a Parr shaker under hydrogen (40 psi) for 2 h. The reaction mixture was filtered through celite and evaporated to give 6.97 g (100%) of 1-isopropyl-1,3-dihydro-benzoimidazol-2-one as a white solid. 1H NMR (CDCl3) delta 1.57 (d, J=7.1 Hz, 6H), 4.70-4.81 (m, 1H), 7.02-7.10 (m, 2H), 7.10-7.20 (m, 2H); MS m/e 177 (MH+); Anal. Calcd for C10H12N2O: C, 68.16; H, 6.86; N, 15.90; Found: C, 68.05; H, 6.63; N, 15.77.

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; Yu, Kuo-Long; Wang, Xiangdong; Sun, Yaxiong; Cianci, Christopher; Thuring, Jan Willem; Combrink, Keith; Meanwell, Nicholas; Zhang, Yi; Civiello, Rita L.; US2003/207868; (2003); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem