Author: Jessica.F

Reference of 5805-57-2, These common heterocyclic compound, 5805-57-2, name is (1H-Benzo[d]imidazol-2-yl)methanamine, 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.

General procedure: 9-Chloroacridine or its derivatives (1.0 mmol) and phenol (10.0 mmol) were added into a 100 ml round-bottom flask and the mixture was stirred for 1 h at 60 C under argon atmosphere. Then benzimidazole derivatives (8a-8n, 8p-8q, 1.2 mmol) were added. The mixture was stirred under 120 C for 2 h. Then the mixture was poured into a mixture of ethyl acetate (50 mL) and N-methyl morpholine (1 ml) to get the crude product as yellow precipitation. The crude product was recrystallized from ethylacetate.

The synthetic route of 5805-57-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gao, Chunmei; Li, Bin; Zhang, Bin; Sun, Qinsheng; Li, Lulu; Li, Xi; Chen, Changjun; Tan, Chunyan; Liu, Hongxia; Jiang, Yuyang; Bioorganic and Medicinal Chemistry; vol. 23; 8; (2015); p. 1800 – 1807;,
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. 3034-38-6, name is 5-Nitro-1H-imidazole, A new synthetic method of this compound is introduced below., Quality Control of 5-Nitro-1H-imidazole

Example 20Preparation of 3-(4-fluorophenylsulfonyl)-N-Q-methyl-lH-imidazol-4- vDisoq uinolin- 1-amine[00277] Step A: To a mixture of 4-nitro-lH-imidazole (2.0 g, 17.7 mmol) andK2CO3 (3.67 g, 26.6 mmol) in acetonitrile (18 mL) was added iodomethane (1.32 mL, 21.2 mmol) and the mixture was heated in a sealed vial at 60 C overnight. The mixture was filtered washing with acetone. The filtrate was concentrated under reduced pressure, and the residue was diluted with hot isopropanol and cooled, and the precipitated solid was collected by filtration. The solid was dissolved in chloroform and filtered, and the filtrate was concentrated under reduced pressure. The residue was triturated with propan-2-ol and collected by filtration to afford 1- methyl-4-nitro-lH-imidazole (1.03 g, 46%) as a tan solid. 1H NMR (300 MHz, DMSO-t/e) delta 8.37 (d, J= 1.1 Hz, 1H), 7.82 (s, 1H), 3.76 (s, 3H).

The synthetic route of 3034-38-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMBIT BIOSCIENCES CORPORATION; FARAONI, Raffaella; HADD, Michael, J.; HOLLADAY, Mark, W.; ROWBOTTOM, Martin; SETTI, Eduardo; WO2012/30944; (2012); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1467-16-9,Some common heterocyclic compound, 1467-16-9, name is 1H-Imidazole hydrochloride, molecular formula is C3H5ClN2, 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.

K2CO3 (3.99 g, 28.8 mmol) and imidazole hydrochloride (1.00 g, 9.60mmol) were dissolved in MeCN (30 mL) in a round-bottomed flask. Benzyl bromide (1.25 mL, 10.6 mmol) was added dropwise to the stirred solution at r.t. After 70 h, the solution was concentrated and the materials redissolved in CH2Cl2 (i.e., CH2Cl2) and then extracted with H2O (3 × 30 mL). The organic layer was then dried (MgSO4). The product was collected as off-white coloured wax (0.63 g, 42% yield). 1H NMR spectrum is consistent with that previously reported.

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

Reference:
Article; Herasymchuk, Khrystyna; Huynh, Jennifer; Lough, Alan J.; Roces Fernandez, Laura; Gossage, Robert A.; Synthesis; vol. 48; 13; (2016); p. 2121 – 2129;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 1450-93-7, 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. 1450-93-7, name is 1H-imidazol-2-amine sulfate(2:1) belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

2-Aminoimidazole sulfate (659 mg) is dissolved in 0.42 mL of concentrated HCl, 1 mL of water, and 3 mL of acetic acid. The resulting solution is cooled to 0 C. To the solution is added 345 mg of NaNO2 in 1 mL of water dropwise so the internal temperature is maintained below 5 C. The resulting yellow-brown solution is stirred for 30 minutes at 0 C. In a separate flask equipped with a mechanical stirrer a mixture of 1.0 g of 2,2,2-trifluoro-1-(4-pentyl-3,4-dihydroquinoxalin-1(2H)-yl)ethan-1-one, 0.82 g of sodium acetate and 3 mL of acetic acid is cooled to 0 C. To this slurry is added the diazonium solution slowly while stirring. After the addition is complete, the resulting red suspension is stirred for 1 hour at 0 C. The dark reaction mixture is poured into a beaker containing 10 g of ice. Aqueous NaOH (20%) is added to the suspension slowly until pH 6.5 is reached. The mixture is filtered and brick red solid is collected. The crude (E)-1-(7-((1H-imidazol-2-yl)diazenyl)-4-pentyl-3,4-dihydroquinoxalin-1(2H)-yl)-2,2,2-trifluoroethan-1-one is dried and used in the next step without further purification (0.94 g).

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-imidazol-2-amine sulfate(2:1), other downstream synthetic routes, hurry up and to see.

Reference:
Patent; The Procter & Gamble Company; MURPHY, Bryan Patrick; ZHANG, Guiru; ZHAO, Jielu; (32 pag.)US2018/72970; (2018); 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 4238-71-5 as follows. Quality Control of 1-Benzyl-1H-imidazole

General procedure: Yield: 82%. Yellow oil. 1H NMR (400HMz, CDCl3, TMS) delta 10.61 (s, 1H), 7.49-7.47 (m, 2H), 7.43(s, 1H), 7.39(s, 1H), 7.34-7.32 (m, 3H), 5.59 (s, 2H), 4.27 (t, J = 6.0 Hz, 2H), 1.90-1.83 (m, 2H), 1.38-1.29 (m, 2H), 0.91(t, J = 6.0 Hz, 3H). 13C NMR (100HMz, CDCl3; TMS) delta 136.12, 134.49, 128.94, 128.68, 128.30, 122.78, 122.50, 51.79, 48.65, 31.23, 18.76, 13.24.

According to the analysis of related databases, 4238-71-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wu, Shi; Wang, Binshen; Zhang, Yongya; Elageed, Elnazeer H.M.; Wu, Haihong; Gao, Guohua; Journal of Molecular Catalysis A: Chemical; vol. 418-419; (2016); p. 1 – 8;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 305790-48-1, 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. 305790-48-1, name is 6-Bromo-1-methyl-1H-benzo[d]imidazol-2(3H)-one belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

[000822j A stirred solution of compound 2 (0.1 g, 1 eq) in POC13 (3 mL) was heated at 110C for 18 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was slowly basified to pH 8 using saturated sodium bicarbonate solution and extracted with ethyl acetate (2 X 25 mL). Combined organic extracts were washed with brine and dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel 100-200 mesh using 50% EtOAc-hexane to afford the title compound 3. LCMS (mlz): 244.95 (M + 1).

The synthetic route of 6-Bromo-1-methyl-1H-benzo[d]imidazol-2(3H)-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; BHAGWAT, Shripad; WANG, Bing; LUEDTKE, Gregory R.; SPYVEE, Mark; (490 pag.)WO2016/57834; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 934-22-5, A common heterocyclic compound, 934-22-5, name is 6-Aminobenzimidazole, molecular formula is C7H7N3, 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.

General procedure: A dry 50 mL flask was charged with 2-halogenated aromatic aldehyde 1 (1.0 mmol), 1H-benzo[d]imidazol-5-amine (0.133 g,1.0 mmol), cyclohexane-1,3-diones (1.0 mmol), CuI (10 mg), L-proline(6 mg), Cs2CO3 (650 mg) and dioxane (10 mL). The reaction mixture was stirred at reflux for 10-18 h. After completion of the reaction, as indicated by TLC, the solid was filtered off by a fast and hot filtration, and the products of 4 were obtained as pale yellow powder or crystals, when the mixture was allowed to cool down to room temperature.

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; Li, Chao; Zhang, Wen-Ting; Wang, Xiang-Shan; Tetrahedron; vol. 70; 46; (2014); p. 8919 – 8924;,
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. 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, A new synthetic method of this compound is introduced below., SDS of cas: 68282-53-1

4-[(3-Carbamoylphenyl)(piperidin-4-yliden e)methyl]-N, N-dimethylbenzamide (40 mg, 11 mmcl) and4-methyl-IH-imidazole-5-carbaldehyde (13.3 mg, 0.12 mmol) were dissolved in dichloroethane (1.5mL). Acetic acid (6.3 pL, 0.11 mmol) was added and the reaction was stirred for 10 minutes at room temperature before NaBH(OAc)3 (37.3 mg, 0.18 mmcl) was added. The reaction mixture was stirred at room temperature for 2 days. Methylene chloride (1 mL) was added and the mixture was washed with water (1 mL). The water phase was extracted with methylene chloride (1 mL x 3). The combined organic phases were dried with Na2SO4, filtered and evaporated. The crude product waspurified by preparative HPLC (10 to 50% CH3CN in 50 mM NH4HCOS(aq)) to give the title compound (14 mg, 28% yield) as a white solid. MS ESI m/z 458 [M+H].

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; PHARMNOVO AB; VON MENTZER, Bengt; STARKE, Ingemar; BRANDT, Peter; (20 pag.)WO2016/99393; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 401567-00-8,Some common heterocyclic compound, 401567-00-8, name is 2-Chloro-1H-benzo[d]imidazole-5-carbonitrile, molecular formula is C8H4ClN3, 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.

A mixture of 2-chloro-1H-benzimidazole~5-carbonitrile (3.0 g, 17 mmol, 1.0 eq), (2S)-2-[(4-tert-0 butylphenoxy)methyl]oxirane (1-2) (3.5 g, 19 mmol, 1.1 eq) and cesium carbonate (0.10 g, 0,31 mmol, 0.020 eq) were heated under microwave irradiation at 130 C for 45 minutes. Ethyl acetate was added (200 ml) and the organic layer was washed with water (50 ml) and dried over sodium sulfate. The residue was purified by silica gel chromatography (0-100% ethyl acetate/hexanes) followed by purification by super critical fluid chromatography (ChiraiPak AS-5 H, 21x250mm, 90/10 CO2/Methanol, 70 ml/min) to separate regioisomers and yield (2S)-2- ( { [tert-butyl(dimethyl )si Iy I ]oxy } methy l)-2 , 3 -dihydro [1,3] oxazolo [3 ,2 -a] benzi midazole-7 – carbonitrile (1-3) as a yellow oil. 1H NMR (400 MHz, CDCl3) delta 7.80 (s, 1H), 7.42 (d, 1H, J = 8.2 Hz), 7.19 (d, 1H, J = 8.2 Hz), 5.51-5.44 (m, 1H), 4.35-4.26 (m, 2H), 4.10 (dd, 1H, J – 1 1.8, 3.8 Hz), 3.95 (d, 1H, J – 3.1 Hz), 0.76 (s, 9 H), 0.00 (s, 6 H). LRMS m/z (M+H) 330.0 found,0 330.2 required. The alternative regioisomer (1-4) was also isolated and characterized.

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

Reference:
Patent; MERCK & CO., INC.; WO2009/140163; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 705-09-9, A common heterocyclic compound, 705-09-9, name is 2-(Difluoromethyl)-1H-benzo[d]imidazole, molecular formula is C8H6F2N2, 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.

A mixture of 2-difluoromethyl-lH-benzimidazole (0.168 g), 4,6-dichloro- 2-morpholinopyrimidine (0.233 g), sodium bicarbonate (0.168 g) and DMA (5 ml) was stirred under nitrogen and heated to 90C for 20 hours. The resultant mixture was cooled, filtered and the filtrate was evaporated. The resultant product was purified by column chromatography on silica using increasingly polar mixtures of ethyl acetate in methylene chloride as eluent. The solid so obtained was washed with a 1 : 1 mixture of isohexane and diethyl ether. There was thus obtained 6-chloro-4-(2-difluoromethylbenzimidazol- 1 -yl)-2-morpholinopyrimidine (0.075 g); NMR Spectrum: (DMSOd6) 3.7 (m, 4eta), 3.78 (m, 4H), 7.2 (s, IH), 7.39-7.72 (m, 3H), 7.84 (d, IH), 7.9 (d, IH); Mass Spectrum: M+H+ 366.

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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BUTTERWORTH, Sam; GRIFFEN, Edward, Jolyon; HILL, George, Beresford; PASS, Martin; WO2008/32089; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem