Category: imidazoles-derivatives

Adding a certain compound to certain chemical reactions, such as: 86718-07-2, name is Ethyl 4-(1-Imidazolyl)benzoate, 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 86718-07-2, HPLC of Formula: C12H12N2O2

Alternatively the 4-(1-imidazolyl)-benzylalcohol can be obtained by reduction of the ethyl 4-(1-imidazolyl)-benzoate with LiAlH4. The 4-(1-imidazolyl)-benzylalcohol thus obtained is solved in diethyl ether and transformed into the corresponding hydrochloride by bubbling gaseous HCl.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Farmitalia Carlo Erba S.R.L.; US5238953; (1993); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 104619-51-4, name is Di(1H-imidazol-1-yl)methanimine, 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 104619-51-4, Safety of Di(1H-imidazol-1-yl)methanimine

To a of solution 5-fluoro-2-nitrophenol (4.77 mmol, 0.75 g) in methanol (50 mL), PtO2 (0.24 mmol, 0.06 g) was added. The reaction was flushed with argon followed by hydrogen for fifteen minutes each with constant magnetic stirring. The reaction was then maintained under hydrogen atmosphere at ordinary pressure (balloon) for fifteen hours. Argon was again flushed through the reaction vessel for 15 minutes. Then the reaction contents were filtered quickly over a thin pad of celite which was then immediately washed with methanol (25 mL). The filtrate was concentrated in vacuo yielding an orange residue. The residue was quickly re-dissolved in acetonitrile (50 mL) and di(imidazole-1-yl)methanimine (11.92 mmol, 1.92 g) was added with constant magnetic stirring. The reaction was then placed under argon atmosphere and gently refluxed for six hours. The reaction was concentrated under reduced pressure and silica gel column chromatography (2:1 hexanes/ethyl acetate) provided a crystalline white solid in a 71% yield. The product of the reduction (2-amino-5-fluorophenol) is air unstable and appropriate measures should be taken to minimize air exposure.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Rynearson, Kevin D.; Charrette, Brian; Gabriel, Christopher; Moreno, Jesus; Boerneke, Mark A.; Dibrov, Sergey M.; Hermann, Thomas; Bioorganic and Medicinal Chemistry Letters; vol. 24; 15; (2014); p. 3521 – 3525;,
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. 288-32-4, name is 1H-Imidazole, A new synthetic method of this compound is introduced below., Safety of 1H-Imidazole

To a solution of 1H-imidazole (42 g, 617 mmol) in dichloromethane (1 L) was added cyanogen bromide (22.5,212 mmol) and the mixture was heated to reflux for 30 minutes,allowed to cool to room temperature and the white solid was filtered off. The filtrate was concentrated to 100 ml andstored in the refrigerator for 3 days. The precipitated solid wasfiltered off to obtain 8 g di(1H-imidazol-l-yl)methanimine(49.6mmol, 8%).

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; BRISTOL-MYERS SQUIBB COMPANY; COOK II, JAMES H; MCDONALD, IVAR M; KING, DALTON; OLSON, RICHARD E; WANG, NENGHUI; IWUAGWU, CHRISTIANA I; ZUSI, F.CHRISTOPHER; MACOR, JOHN E; (330 pag.)JP5714745; (2015); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 2620-76-0,Some common heterocyclic compound, 2620-76-0, name is 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, molecular formula is C19H13BrN2, 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.

[Example 4] This example will give descriptions of a method of synthesizing 2-[4-(6-phenyldibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation: DBTBIm-IV) represented by the following Structural formula (188). [Show Image] [Synthesis of 2-[4-(6-phenyldibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation: DBTBIm-IV)] The synthesis scheme of 2-[4-(6-phenyldibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation: DBTBIm-IV) is illustrated in (B-4). [Show Image] In a 100-mL three-neck flask, a mixture of 1.7 g (5.0 mmol) of 2-(4-bromophenyl)-1-phenyl-1H-benzimidazole, 1.5 g (5.0 mmol) of 6-phenyldibenzothiophen-4-boronic acid, 22 mg (0.1 mmol) of palladium(II) acetate, 60 mg (0.2 mmol) of tri(ortho-tolyl)phosphine, 20 mL of toluene, 2 mL of ethanol, and 7.5 mL of a 2 mol/L aqueous solution of potassium carbonate was stirred to be degassed under reduced pressure. Then, the mixture was heated and stirred at 90 °C for 2.5 hours under a nitrogen stream. After a predetermined time, 150 mL of toluene was added to this mixture solution, and the organic layer of the resulting suspension was suction filtered through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855). The resulting filtrate was concentrated, followed by purification using silica gel column chromatography. The silica gel column chromatography was carried out using a mixed solvent of toluene and ethyl acetate in a ratio of 19 to 1 as a developing solvent. The obtained fractions were concentrated, and acetone and methanol were added to the mixture, followed by irradiation with ultrasonic waves. The precipitated solid was collected by suction filtration. Thus, 2.2 g of a white powder was obtained in 83percent yield, which was the substance to be produced. The Rf values of the produced substance and 2-(4-bromophenyl)-1-phenyl-1H-benzimidazole were respectively 0.21 and 0.36, which were found by silica gel thin layer chromatography (TLC) (with a developing solvent containing ethyl acetate and hexane in a ratio of 1 to 5). The nuclear magnetic resonance (NMR) measurement identified this compound as 2-[4-(6-phenyldibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation: DBTBIm-IV). 1H NMR data of the obtained compound are as follows: 1H NMR (CDCl3, 300 MHz): delta (ppm) = 7.26-7.59 (m, 15H), 7.64-7.71 (m, 6H), 7.90-7.93 (d, J = 7.8 Hz, 1H), 8.15-8.19 (m, 2H). FIGS. 18A and 18B illustrate the 1H NMR charts. Note that FIG. 18B is a chart showing an enlarged part of FIG. 18A in the range of 7.0 ppm to 8.5 ppm. Further, FIG. 19A shows an absorption spectrum of a toluene solution of DBTBIm-IV, and FIG. 19B shows an emission spectrum thereof. FIG. 20A shows an absorption spectrum of a thin film of DBTBIm-IV, and FIG. 20B shows an emission spectrum thereof. The absorption spectrum was measured using an ultraviolet-visible spectrophotometer (V-550, produced by JASCO Corporation). The measurements were performed with samples prepared in such a manner that the solution was put in a quartz cell while the thin film was obtained by evaporation onto a quartz substrate. The absorption spectrum of the solution was obtained by subtracting the absorption spectra of quartz and toluene from those of quartz and the solution, and the absorption spectrum of the thin film was obtained by subtracting the absorption spectrum of a quartz substrate from those of the quartz substrate and the thin film. In FIGS. 19A and 19B and FIGS. 20A and 20B, the horizontal axis represents wavelength (nm) and the vertical axis represents intensity (arbitrary unit). In the case of the toluene solution, an absorption peak was observed at around 316 nm and emission wavelength peaks were 371 nm and 387 nm (excitation wavelength: 320 nm). In the case of the thin film, absorption peaks were observed at around 242 nm, 304 nm, and 319 nm, and an emission wavelength peak was 402 nm (excitation wavelength: 349 nm).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, its application will become more common.

Reference:
Patent; SEMICONDUCTOR ENERGY LABORATORY CO., LTD.; EP2354135; (2011); 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 1072-84-0 as follows. Safety of 1H-Imidazole-4-carboxylic acid

To a solution containing Intermediate 54 (0. 041g) in N, N-DIMETHYLFORMAMIDE (3ML) were added imidazole-4-carboxylic acid (0. 012g, ALDRICH), (1H-1, 2, 3-benzotriazol-1-yloxy) (TRI-1- pyrrolidinyl) phosphonium hexafluorophosphate (PyBop) (0. 053g) and N, N- diisopropylethylamine (0. 03ML). The solution was stirred under nitrogen at room temperature for 18h and was then concentrated in vacuo. The residual gum was purified using an aminopropyl SPE cartridge eluting with methanol followed by chromatography on silica gel (SPE cartridge), eluting with a gradient of 0% to 8% methanol in chloroform, to give the title compound as a yellow solid (0. 031g). LC/MS Rt 2. 32 min, M/Z 549 [MH+]

According to the analysis of related databases, 1072-84-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2004/103998; (2004); 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 934-22-5 as follows. Recommanded Product: 934-22-5

General procedure: A mixture of compound II-1, II-2 or II-3 (2 mmol),SnCl2·2H2O (10 mmol) in EtOAc (15 mL) was refluxed for12 h. When the reaction was complete according to TLCanalysis, the resulting reaction mixture was cooled to room temperature. Subsequently, the reaction mixture wasadjusted to pH 8-9 with saturated aq. NaHCO3 (50 mL).Then the mixture was extracted with EtOAc (2 × 150 mL).The combined organic phase was washed with brine (200mL), dried over anhydrous Na2SO4, and concentrated toafford compounds III-1, III-2 or III-3, which were useddirectly for the next step without further purification. To amixture of 5-amino-1H-benzimidazole (III-1, III-2 or III-3,2 mmol), water (5 mL) and concentrated HCl (12 mol/L,0.51 mL) at 0C, a solution of sodium nitrite (NaNO2, 2.1mmol) in water (10 mL) was added dropwise whilemaintaining the temperature below 5C. After stirring for 20min, a solution of diazonium chloride was prepared.Subsequently, a solution of diazonium chloride was addedgradually to a mixture of phenols (IV-1-IV-10, 2 mmol),sodium hydroxide (NaOH, 2 mmol), ethanol (15 mL) andwater (25 mL) at 0-5C. After the addition of the abovediazonium solution, the mixture was continued to stir for 3-6h until a lot of precipitate was produced. The solid wascollected, washed with water (3×10 mL), dried and purifiedby PTLC to give the target products V-1~V-28.

According to the analysis of related databases, 934-22-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ke, Yazhen; Zhi, Xiaoyan; Yu, Xiang; Ding, Guodong; Yang, Chun; Xu, Hui; Combinatorial Chemistry and High Throughput Screening; vol. 17; 1; (2014); p. 89 – 95;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 152628-02-9, These common heterocyclic compound, 152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]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.

General procedure: A solution of an appropriate benzimidazole (5.03mmol) and NaH (0.12g, 5.53mmol, 60%) in 100mL anhydrous THF was stirred for 30minat 50C. After cooling to rt, a mixture of an appropriate bromide (6.04mmol) in anhydrous THF (50mL) was added dropwise to the solution. The solution was stirred for 3hat 50C. Then the resulting mixture was poured into 30mL ice water, and extracted with ethyl acetate (50mL×3). The combined organic layer was dried over MgSO4. After filtration, the solvent was removed under reduced pressure and the residue was purified by CC to give the product as white solid 4.1.7.3 [4-[[2-Propyl-4-methyl-6-(1-methylbenzimidazol-2-yl)benzimidazole-1-yl]methyl]-1H-indol-1-yl](phenyl)methanone (12c) 12c was prepared by following the above general procedure. Yield: 91.9%. MP: 214-216 C. 1H NMR (400 MHz, CDCl3): delta 8.34 (d, 1H), 8.04 (s, 1H), 7.27-7.73 (m, 12H), 6.74 (d, 1H), 6.52 (d, 1H), 5.67 (s, 2H), 3.89 (s, 3H), 2.89 (t, 2H), 2.78 (s, 3H), 1.85 (m, 2H), 1.02 (t, 3H). MS (ESI): [M + H]+ calcd 538.3; found 538.3.

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

Reference:
Article; Zhu, Weibo; Bao, Xiaolu; Ren, He; Da, Yajing; Wu, Dan; Li, Fuming; Yan, Yijia; Wang, Li; Chen, Zhilong; European Journal of Medicinal Chemistry; vol. 115; (2016); p. 161 – 178;,
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 15469-97-3 as follows. HPLC of Formula: C22H18N2

Compounds 6 and 7: To a solution of tritylimidazole (2.67 g, 8.6 mmol) in THF (85 ml) cooled to -20 C a stock 1.6 M solution n-butyl lithium in hexanes (5.13 ml, 8.2 mmol) was added dropwise. The resulting wine red coloured solution was allowed to warm up to RT and stirred for 30 min. The solution was then cooled to -78 C and a solution of aldehyde (4.17 g, 7.8 mmol) in THF (15ml) was added dropwise. The resulting solution was stirred for 30 min and then allowed to warm to RT in 30 min. The reaction was quenched by addition of ammonium chloride solution and extracted with ethyl acetate. The aqueous layer was extracted with ethyl acetate once more. The combined organic layer was dried and evaporated. The residue was purified by flash column chromatography in PE-EA gradient 10-20-30percent to give 1.18 g (1.4 mmol, 18percent) of 6 (Rf = 0.55 PE- EA 20percent) and 3.48 g (4.13 mmol, 53percent) of 7 (Rf = 0.4 PE-EA 20percent) .6: [?]D = -10.5 c 1.24 CHCl3HRMS: Positive mode, m/z = 845.4344; expected for C54H6IN2O5Si [M+H]+ = 845.4350.?H (500 MHz) : 0.0 and 0.02 (6H, 2*s, -Si (CH3) C (CH3) 3) , 0.89 (9H, s, -Si(CH3)C(CH3)S) , 2.94 (IH, dd, J4, 5 = 6.5 Hz, J4/3 = 4.1 Hz, H-4) , 3.1 (IH, bs, 2-OH) , 3.14 (IH, dd, J6a,5 = 5.4, Jea,6b = 10.2 Hz, H-6a) , 3.37 (IH, dd, J6b,5 = 3 Hz, H- 6b) , 3.8 (IH, dd, J3, 2 = 3.2 Hz, H-3) , 3.93 (IH, ddd, H-5) , 3.97 and 4.41 (2H, AB spectrum, Jgem = 11.5 Hz, PhCH2O-) , 4.3 (IH, bs, H-2) , 4.33 (2H, s, PhCH2O-) , 4.71 and 4.93 (2H, AB spectrum, Jgem = 11.2 Hz, PhCH2O-) , 6.78 (IH, m) , 7.02 (2H, m) , 7.13-7.4 (28H, m) .?c (125 MHz) : -4.4, 18.2, 26.1, 66.6 (C-2) , 72.8 (C-6) , 72.9 (C-5) , 73.2, 73.8, 74.4, 75.3, 78.8 (C-3) , 81.7 (C-4) , 122.2, 126.08, 127.06, 127.3, 127.4, 127.8, 128.1, 128.3, 128.5, 130, 138.6, 138.8, 138.9, 142.9, 150.7.7: [?]D = -67.5 c 1.34 CHCl3HRMS: Positive mode, m/z = 845.4344; expected for C54H6IN2O5Si [M+H]+ = 845.4350.?H (500 MHz) : -0.09 and 0.0 (6H, 2*s, -Si (CH3) C (CH3) 3) , 0.82 (9H, s, -Si (CH3) C (CH3) 3) , 3.52 (IH, dd, J6a,5 = 6.5 Hz, J6a,6b = 10.4 Hz, H-6a) , 3.73 (IH, dd, J4, 5 = 7.3, J4, 3 = 2.6 Hz, H- A) 1 3.78 (IH, dd, J6b,5 = 2.2 Hz, H-6b) , 4.12 (IH, ddd, J5, 4 =6.7 Hz, H-5) , 4.24 (IH, dd, J3, 2 = 8.7 Hz, H-3) , 4.27 and 4.57 (2H, AB spectrum, Jgem = 12.4 Hz, PhCH2O-) , 4.41 (2H, s, PhCH2O-) , 4.48 and 4.6 (2H, AB spectrum, Jgem = 10.7 Hz, PhCH2O-) , 4.5 (IH, dd, J2, 0H = 4 Hz, H-2) , 6.79 (IH, m) , 6.85-7.4 (31H, m) .?c (125 MHz) : -4.7, 18.2, 26, 65.9 (C-2) , 72.6 (C-5) ,73.1, 73.2 (C-6) , 73.8, 75.5, 79.6 (C-4) , 80.13 (C-3) , 122.3, 125.9, 126.17, 126.5, 127, 127.2, 127.6, 127.8,127.9, 128.1, 128.4, 128.6, 130, 130.2, 138.7, 139, 139.3, 141, 142.5, 150.2 (C-I) .

According to the analysis of related databases, 15469-97-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE UNIVERSITY COURT OF THE UNIVERSITY OF DUNDEE; WO2008/59267; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 36947-68-9, name is 2-Isopropyl-1H-imidazole, molecular formula is C6H10N2, 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. Application In Synthesis of 2-Isopropyl-1H-imidazole

General procedure: To a stirred solution of indole (1.0 mmol)/Imidazole (1.2 mmol) in DMSO was added 1,3-diyne (1.0 mmol), CuI (0.1 mmol), 1,10-phenanthroline (0.05 mmol) and cesium carbonate (1.5 mmol). The reaction mixture was heated at 100 C for 5-16 h and the completion of the reaction was monitored by TLC. After completion of the reaction, it was cooled down to room temperature and then diluted with H2O (5 mL) followed by extraction of the product with EtOAc (3 × 10 mL). The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and the solvent was removed in vacuo. The crude product was purified on a silica gel column using hexane: ethyl acetate as eluent. The Z isomer was crytalised using DCM/EtOH in indole and EtOH in case of imidazole.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 36947-68-9, its application will become more common.

Reference:
Article; Gupta, Sahaj; Agarwal, Piyush K.; Saifuddin, Mohammad; Kundu, Bijoy; Tetrahedron Letters; vol. 52; 44; (2011); p. 5752 – 5757;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 3034-38-6, The chemical industry reduces the impact on the environment during synthesis 3034-38-6, name is 5-Nitro-1H-imidazole, I believe this compound will play a more active role in future production and life.

To a solution of 4-nitro-1H- imidazole (260 mg, 2.299 mmol) in DMF (5 mL) was added 1.0 M NaHMDS/THF (2.53 mL, 2.53 mmol) dropwise at rt. After stirring at rt for 20 min, 1-bromopropan-2-one (315 mg, 2.299 mmol) was added very slowly. The mixture was stirred at rt for ON. Water was added and extracted with EtOAc (4 x 50 mL). The organic layer was concentrated. The residue was purified via silica gel chromatography (12g, DCM-10%MeOH) to give 1-(4-nitro-1H-imidazol-1-yl)propan-2-one (180 mg, 1.064 mmol, 46 % yield). (2333) MS ESI m/z 170.0 (M+H)+ (2334) 1H NMR (499 MHz, CD3OD) delta 8.06 – 8.04 (m, 1H), 7.66 – 7.62 (m, 1H), 5.17 – 5.12 (m, 1H), 2.28 (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, 5-Nitro-1H-imidazole, other downstream synthetic routes, hurry up and to see.

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