Month: August 2021

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. 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 39021-62-0

n-BuLi (2.5 M in hexanes, 0.52 mL, 1.3 mmol) was added dropwise to a solution of 6-bromo-2,4-dichloro-3-phenylquinoline (353 mg, 1 mmol, Intermediate 1: step c) in dry THF (10 mL) in a 100 mL three necked round bottomed flask at -78 C. under N2. Stirring was continued for 30 minutes then a solution of 1-methyl-1H-imidazole-5-carbaldehyde (110 mg, 1 mmol) in dry THF (10 mL) was added at -78 C. The cooling bath was removed and the mixture was gradually warmed up to room temperature and stirred for 2 hours. The mixture was quenched by adding H2O (10 mL) and then extracted with CH2Cl2 (2*50 mL). The combined organic phase was dried over Na2SO4, concentrated to dryness and purified by prep-TLC (developed by CH3OH/CH2Cl2 1:5) to afford the title compound as a white solid. MS (ESI): 384.1 [M+H]+. 1H NMR (300 MHz, CD3OD) delta ppm 8.45 (s, 1H), 7.94 (dd, J=42.2, 8.0 Hz, 2H), 7.73-7.24 (m, 6H), 6.56 (s, 1H), 6.16 (s, 1H), 3.70 (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 39021-62-0.

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.; US2015/105372; (2015); 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 305790-48-1 as follows. category: imidazoles-derivatives

5-bromo~l-(2,2-diraethylpropyl)-3-raethyl-l,3-dihydro-2H»benziraidazol-2~one (1-5)A solution of 6-bromo-l -methyl- 1, 3 -dihydro-2H-benzimidazol-2-one (1-4, 500 mg, 2.20 mmol) in DMF (10 ml) was treated with Sodium hydride (176 mg, 4.40 mmol, 2.0 eq) followed by the l-Iodo-2,2-Dimethylpropane (585 muEpsilon, 4.40 mmol, 2.0 eq). The reaction was irradiated at 175 deg C for 20 min in a microwave. The reaction was complete by LC/MS, so it was partitioned between EtOAc (2×125 ml) and water (150 ml). The combined organic layers were dried over Na SO4 and concentrated. The crude maroon-orange oil was purified via flash column chromatography (Si02: 100% Hex to 60:40 Hex:EtOAc), affording the title compound, 5-bromo-l-(2,2-dimethylpropyl)-3-methyl-l,3-dihydro-2H-benzimidazol-2-one (1-5), as a yellow solid with >95% purity. ‘HNMR (600 MHz, CDC13) delta 7.18 (dd, 1H, J= Hz), 7.10 (s, H), 6.88 (d, IH, J- Hz), 3.63 (s, 2H), 3.40 (s, 3H), 1.02 (s, 9H). LRMS m/z: Calc’d for C7H7Br 202 (M.+H) 232.1, found 232.8.

According to the analysis of related databases, 305790-48-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DUDKIN, Vadim; FRALEY, Mark, E.; ARRINGTON, Kenneth, L.; LAYTON, Mark, E.; RODZINAK, Kevin, J.; PERO, Joseph, E.; REIF, Alexander, J.; WO2012/21382; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 3034-38-6, 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. 3034-38-6, name is 5-Nitro-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 4-nitro-1H- imidazole (500 mg, 4.42 mmol) in DMSO (3 mL) was added but-3-en-2-one (465 mg, 6.63 mmol) followed by DMAP (32.4 mg, 0.265 mmol). The mixture was stirred at 70 C for 1.5 h. Water was added and extracted with EtOAc (3 x 50 mL). The organic layer was dried over Na2SO4 and concentrated to give 4-(4-nitro-1H-imidazol-1-yl)butan-2-one (420 mg, 2.293 mmol, 52 % yield). (2354) MS ESI m/z 184.0 (M+H)+ (2355) 1H NMR (499 MHz, CDCl3) delta 7.82 (d, J=1.5 Hz, 1H), 7.50 (d, J=1.4 Hz, 1H), 4.35 – 4.31 (m, 2H), 3.01 (t, J=6.0 Hz, 2H), 2.23 (s, 3H).

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WATTERSON, Scott Hunter; ANDAPPAN MURUGAIAH SUBBAIAH, Murugaiah; DZIERBA, Carolyn Diane; GONG, Hua; GUERNON, Jason M.; GUO, Junqing; HART, Amy C.; LUO, Guanglin; MACOR, John E.; PITTS, William J.; SHI, Jianliang; VENABLES, Brian Lee; WEIGELT, Carolyn A.; WU, Yong-Jin; ZHENG, Zhizhen Barbara; SIT, Sing-Yuen; CHEN, Jie; (810 pag.)WO2019/147782; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 760212-58-6, 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. 760212-58-6 name is 1-(4-Bromophenyl)-2-phenyl-1H-benzo[d]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.

SYNTHESIS EXAMPLE 1 (Synthesis of Compound 1); Into a 100-mL three-necked flask, 3.0 g (8.6 mmol) of 1-(4-bromophenyl)-2-phenyl-1H-benzimidazole, 2.2 g (8.7 mmol) of bis(pinacolato)diboronic acid, 0.21 g (0.29 mmol) of [1,1′-bis(diphenylphosphino)ferrocene] dichloropalladium (II), 2.5 g (25 mmol) of potassium acetate, and 50 ml of DMF were charged and the mixture was heated at 80 C for 3 h in argon flow. After confirming the disappearance of the starting boron compound, the mixture was cooled to room temperature. After adding 2.2 g (8.6 mmol) of 9-bromophenanthrene, 0.21 g (0.29 mmol) of [1,1′-bis(diphenylphosphino)ferrocene] dichloropalladium (II), and 21 mL of a 2 M aqueous solution of sodium carbonate, the mixture was further heated at 80 C for 3 h under stirring. After the reaction, water was added. The precipitated crystals were corrected by filtration, washed with water and methanol, and dried under reduced pressure, to obtain a crude reaction product, which was then purified by a column chromatography (silica gel, dichloromethane: hexane), to obtain 2.5 g of white crystals. The obtained crystals were identified to Compound 1 by FD-MS (field desorption mass spectrometry). Yield: 65%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(4-Bromophenyl)-2-phenyl-1H-benzo[d]imidazole, and friends who are interested can also refer to it.

Reference:
Patent; Idemitsu Kosan Co., Ltd.; EP2236501; (2010); 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. 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 41716-18-1

To a solution of 1-methyl-1Himidazole-4-carboxylic acid (0.50 g, 4.0 mmol), 1-hydroxybenztriazole monohydrate (0.74 g, 4.8 mmol), and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (0.92 g, 4.8 mmol) in acetonitrile (10 mL) was added a solution of 3-(trifluoromethoxy) benzylamine 8(0.84 g, 4.4 mmol) in acetonitrile (10 mL), and the mixture was stirred at room temperature for overnight. The reaction mixture was concentrated in vacuo, and saturated aqueous NaHCO3solution was added to the residue. After extraction with ethyl acetate, the organic layer was dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was purified using silica gel column chromatography (0?10percent MeOH in CHCl3) to obtain 9(1.18 g, 98percent) as a colorless powder.1H-NMR (600 MHz, CDCl3) delta: 3.73 (3 H, s), 4.62 (2 H, d, J=6.0 Hz), 7.08?7.13 (1 H, m), 7.18 (1 H, s), 7.26?7.29 (1 H, m), 7.31?7.37 (2 H, m), 7.44?7.51 (1 H, m), 7.55 (1 H, d, J=1.4 Hz); MS ESI: m/z300 [M+H]+.

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 41716-18-1.

Reference:
Article; Yamamoto, Shuji; Ohta, Hiroshi; Abe, Kumi; Kambe, Daiji; Tsukiyama, Naohiro; Kawakita, Yasunori; Moriya, Minoru; Yasuhara, Akito; Chemical and Pharmaceutical Bulletin; vol. 64; 11; (2016); p. 1630 – 1640;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 57090-88-7, 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 57090-88-7 as follows.

a) 1-(2-Trimethylsilanyl-ethoxymethyl)-1H-imidazole-4-carbonitrile A flask charged with imidazole-4-carbonitrile (0.5 g, 5.2 mmol) (Synthesis, 677, 2003), 2-(trimethylsilyl)ethoxymethyl chloride (SEMCl) (0.95 mL, 5.3 mmol), K2CO3 (1.40 g, 10.4 mmol), and acetone (5 mL) was stirred for 10 h at RT. The mixture was diluted with EtOAc (20 mL) and washed with water (20 mL) and brine (20 mL) and the organic layer dried over MgSO4. The crude product was eluted from a 20-g SPE cartridge (silica) with 30percent EtOAc/hexane to give 0.80 g (70percent) of the title compound as a colorless oil. Mass spectrum (CI (CH4), m/z) Calcd. for C10H17N3OSi, 224.1 (M+H). found 224.1.

According to the analysis of related databases, 57090-88-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Illig, Carl R.; Ballentine, Shelley K.; Chen, Jinsheng; Meegalla, Sanath K.; Rudolph, M. Jonathan; Wall, Mark J.; Wilson, Kenneth J.; Desjarlais, Renee L.; Manthey, Carl L.; Molloy, Christopher J.; US2008/51402; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 106429-59-8,Some common heterocyclic compound, 106429-59-8, name is 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carbaldehyde, molecular formula is C8H6N2O2, 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 stirred mixture of intermediate 62 (120 mg, 0.32 mmol), 2-oxo-2,3-dihydro-1Hbenzo[d]imidazole-S-carbaldehyde (CAS: 106429-59-8) (104 mg, 0.64 mmol) and TiG-PrO)s (92 mg, 0.32 mmol) in DCE/DMSO(6 mL/2 mL) at 0 C was added NaBH(OAc); (205 mg, 0.97 mmol) in portions. The reaction mixture was stirred at room temperature overnight. The reaction was quenched with aq. NaHCOsand the resultant was extracted with DCM. The combined organic extracts were washed with brine, dried over anhydrous Na2SQOuq,filtered and concentrated. The residue was purified by prep-HPLC (Waters 2767/Qda, Column: Waters Xbridge 19*150 mm 10 um, Mobile Phase A: H,O (0.1% TFA), B: ACN) to give Compound 117 (22 mg TFA salt, yield: 13%) as a white solid.

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

Reference:
Patent; JANSSEN PHARMACEUTICA NV; JOHNSON & JOHNSON (CHINA) INVESTMENT LTD.; DAI, Xuedong; QUEROLLE, Olivier Alexis Georges; KROSKY, Daniel Jason; CAI, Wei; FU, Liqiang; KONG, Linglong; LIU, Yingtao; WAN, Zhao-Kui; HERKERT, Barbara; PANDE, Vineet; EDWARDS, James Patrick; PATRICK, Aaron Nathaniel; ANGIBAUD, Patrick Rene; PONCELET, Virginie Sophie; (488 pag.)WO2019/120209; (2019); 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. 496-46-8, name is Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, A new synthetic method of this compound is introduced below., Formula: C4H6N4O2

In a 1,000-liter reactor was charged 320 kg of water, Heated to reflux, 71 kg of glycoluril and 58 kg of 50% glyoxal were successively added, Stirring to clear, In the refluxing state, 500 L of a sodium hydroxide solution (8 mol / l) was rapidly added dropwise, After completion of the dropwise addition, The refluxing reaction was continued for 8 hours. Close the heating,When the temperature naturally cool to room temperature,45 kg of chlorine gas was introduced into the reaction system,After completion of the reaction,Concentrated hydrochloric acid was added to adjust the pH to 1,Stirring was reduced to room temperature,After 2 hours,Obtain crude orotic acid.In the 2000-liter reactor, the crude orotate was added and 600 kg of water was added. After boiling, add the concentrated ammonia to dissolve, then add 5 mol / L sulfuric acid to adjust the pH to weak acidity, add activated carbon to boil for 30 minutes, filter it hot, adjust the pH to 1 with concentrated sulfuric acid, Dry, get whey acid finished 25.7 kg, yield 33%, purity 99.9%.

The synthetic route of 496-46-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chengdu Baishixing Science and Technology Industry Co., Ltd.; Shi, Changqing; (6 pag.)CN106187918; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 13435-22-8,Some common heterocyclic compound, 13435-22-8, name is 1-Butyl-2-methyl-1H-imidazole, molecular formula is C8H14N2, 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.

Ex is of a 1-butyl-2-methyl-3(propyl-3-sulfonyl) imidazolium 1-Butyl-2-methylimidazol (710 mg, 0.9 mmol, 1 equivalent) was dissolved in 10 ml toluene and propanesultone (610 mg, 0.9 mmol, 1 equivalent) was added. The clear solution was heated at reflux temperature for 3h at which time a some withe precipitate was formed. The reaction mixture was cooled to room temperature and the white suspension was then filtered and washed with 5 ml toluene. The white solid was dried under high vacuum at 60C for 4 h, yielding the desired product (89 mg, 38% yield). H NMR analysis confirms the structure and a purity of >98 %. Melting point by DSC: 160 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Butyl-2-methyl-1H-imidazole, its application will become more common.

Reference:
Patent; ECOLE D’INGENIEURS ET D’ARCHITECTES DE FRIBOURG; MARTI, Roger; VANOLI, Ennio; AEBY, Sandrine; FISCHER, Fabian; HAPPE, Manuel; WO2013/8172; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 13275-42-8, The chemical industry reduces the impact on the environment during synthesis 13275-42-8, name is 2-(2-Bromophenyl)-1H-benzo[d]imidazole, I believe this compound will play a more active role in future production and life.

General procedure: An oven-dried Schlenk tube equipped with a Teflon valve was charged with a magnetic stir bar, Cu(OAc)2 (18 mg, 0.1 mmol, 20 mol%), NaOEt (68 mg, 1.0 mmol), 1,10-phenanthroline monohydrate (40 mg, 0.2 mmol, 40 mol%), 2-(2-bromophenyl)-1H-benzo[d]imidazole 4 (0.5 mmol), and N-heterocycle 2 (0.5 mmol). The Schlenk tube was evacuated and backfilled with O2 (this procedure was repeated three times). Under a counter flow of O2, DMF (2.0 mL) was added using a syringe. The reaction mixture was stirred at 140 C for 24 h. After the reaction was completed, the mixture was extracted with dichloromethane (3 × 15 mL), and then the organic layer was washed with brine (3 × 10 mL) and dried over anhydrous Na2SO4. Subsequently, the solvent was removed, and the product was purified by column chromatography on silica gel using a mixture of dichloromethane and methanol as the eluent, affording the pure products

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

Reference:
Article; Chen, Dingben; Huang, Ling; Yang, Jianguo; Ma, Junna; Zheng, Yingying; Luo, Yi; Shen, Yang; Wu, Jiashou; Feng, Chao; Lv, Xin; Tetrahedron Letters; vol. 59; 21; (2018); p. 2005 – 2009;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem