Category: imidazoles-derivatives

Reference of 641571-11-1, 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 641571-11-1 as follows.

Method II; To a flask was added 6-methyl-5-[4-(pyrid-3-yl)pyrimid-2-ylamino) nicotinic acid (30.7 g) and SOCl2 (500 mL) and the reaction mixture was refluxed for 4 hours. The reaction mixture was concentrated under reduced pressure to give a solid, which is used for the next step directly. To the above acid chloride was added a clear solution of 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline (24.1 g) in pyridine (200 mL) and the reaction mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure, and then the residue was added with chloroform (500 mL) and water (500 mL) and extracted. The organic phase was dried, filtrated, concentrated, and purified through column chromatography to give the titled compound.

According to the analysis of related databases, 641571-11-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sun, Piaoyang; EP1840122; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1072-62-4, These common heterocyclic compound, 1072-62-4, name is 2-Ethyl-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.

40 mmol of 2-ethylimidazole was dissolved in 20 ml of dimethylsulfoxide (DMS0), and the mixture was milledNa0H80mmol, heated to 60 C, then add 40mmol chloromethyl benzotriazole, 60 C water bath heating lh, cooling to room temperature,Poured into 100g ice water, stirring, precipitation, filtration, precipitation washed 3 times with water to get crude;The crude product was recrystallized from ethyl acetate to give the colored crystals as the ligand 1- (benzotriazole-1-methyl) -1- (2-ethylimidazole).

Statistics shows that 2-Ethyl-1H-imidazole is playing an increasingly important role. we look forward to future research findings about 1072-62-4.

Reference:
Patent; Henan College of Traditional Chinese Medicine; Wang, Xia; Zhang, Chao; Ceng, Dai; Cheng, Di; Song, Ning; Yang, Huai Xia; (11 pag.)(2016);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 1615-14-1, A common heterocyclic compound, 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol, molecular formula is C5H8N2O, 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.

Into a round bottom flask was added 057 (2.331 g, 0.003345 mol), triphenylphosphine (1.14 g, 0.00435 mol) and tetrahydrofuran (13.6 mL, 0.167 mol). The mixture was cooled to O0C under a nitrogen atmosphere. Imidazole ethanol fragment (0.450 g, 0.00401 mol) was added, followed by addition on diethyl azodicarboxylate (0.685 mL, 0.00435 mol). The reaction was allowed to warm slowly to room temperature while stirring. A TLC test revealed an intense product spot together with some unreacted starting material. The reaction was cooled to O0C and an additional 0.2eq of the amine, triphenylphosphine, and DEAD were added. The ice bath was removed and reaction was allowed to warm to room temperature. After 30min, TLC showed the reaction was complete and all starting material was consumed. All solvent was removed under high vacuum. The residue was dissolved in MTBE, the mixture was cooled in an ice bath and some of the triphenyl phosphate was filtered off. The residue was purified on 4Og column, using 0-5%MeOH/DCM. Product fractions containing compound 066 were combined and concentrated down to a residue. Yield: 3.65g(100%).

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; EISAI R & D MANAGEMENT CO., LTD.; WO2009/15368; (2009); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 1792-40-1, 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. 1792-40-1, name is 2-Methyl-5-nitro-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

In a 150 mL round-bottomed flask, the benzimidazole compound represented by Formula III (R1 is methyl, R2 is H, R3 is nitro) (0.361 g, 2.04 mmol) was added, and potassium carbonate was used as a base (0.324 g, 2.35 mmol) of acetonitrile as solvent. After stirring at 70C for 30 minutes, the mixture was cooled to room temperature and Compound II (0.400 g, 1.57 mmol) was added to continue the reaction and the temperature was raised to 70C. TLC followed the reaction to completion. After concentration, extraction, column chromatography, drying and other post-treatments, compound IV-3 (0.449 g) was obtained with a yield of 66.1%.

The synthetic route of 2-Methyl-5-nitro-1H-benzo[d]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Southwest University; Zhou Chenghe; Man Nabaonei·lamohan·laao·yadafu; Ge Pala·lawaya; Wang Yanan; Fang Xuejie; (27 pag.)CN107721933; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 693-98-1, 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. 693-98-1, name is 2-Methyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Synthesis of 2-methyl-1-aryl-1H-imidazole 5: To a stirring solution of 2-methyl- 1H-imidazole 4 (800 mg, 9.74 mmol) in 6 mL anhydrous dimethyl sulfoxide under argon was added iodobenzene (1.09 mL, 9.74 mmol), copper(I) iodide (185 mg, 0.97 mmol) and anhydrous potassium carbonate (2.69 g, 19.49 mmol). The reaction mixture was then heated to 130 C and allowed to stir for 48 hours in a sealed tube. Following completion of the reaction, the mixture was transferred to a separatory funnel containing ethyl acetate (200 mL) and the crude product was washed with water (4×40 mL) and brine (2×30 mL) before the organic layer was collected and dried with anhydrous sodium sulfate, filtered, and concentrated in vacuo. The product was purified via flash column chromatography using hexanes :ethyl acetate (1:1 to 1:4) to elute pure 2-methyl-i -phenyl- 1H-imidazole 5 as a clear oil (730 mg, 47%). [00264] Yield: 47% yield; 730 mg of 5 was isolated as a clear oil. ?H NMR (400 MHz, CDC13): 7.51 -7.37 (m, 3H), 7.30 -7.22 (m, 2H), 6.98 (dd, J = 9.7, 1.4 Hz, 2H), 2.35 (s, 3H). ?3C NMR (100 MHz, CDC13): 144.8, 138.2, 129.6, 128.3, 127.8, 125.6, 120.8, 13.9.Note: NMR spectra match those previously reported.?

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-Methyl-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITY OF FLORIDA RESEARCH FOUNDATION, INCORPORATED; HUIGENS, Robert, William; ABOUELHASSAN, Yasmeen; BASAK, Akash; (220 pag.)WO2018/106922; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 3752-24-7, name is 4,5,6,7-Tetrahydro-1H-benzo[d]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 3752-24-7, name: 4,5,6,7-Tetrahydro-1H-benzo[d]imidazole

A mixture of 4,5,6,7-tetrahydro-1H-benzo[d]imidazole (5.00 g, 40.9 mmol), 90% KOH (3.74 g, 60 mmol) and DMSO (70 mL) was stirred under argon and heated at 40 C for 2 h. After cooling to 10 C, 1-bromohexane (6.3 mL, 45 mmol) was addedin one portion, and the resulting mixture was stirred and heated at 40 C for 4 days.The reaction mixture was poured into ice/water (600 mL), treated with 5 N NaOH(100 mL) and extracted with DCM (2 x 400 mL). The extract was washed with water(300 mL), dried over Na2SO4, and the solvent was removed under reduced pressureto give a residue. Column chromatography of the residue (silica gel, ethylacetate/methanol, 97:3) afforded pure 1-hexyl-4,5,6,7-tetrahydro-1H-benzo[d]imidazole (6.54 g, 77% yield).

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; NITTO DENKO CORPORATION; STANISLAW, Rachwal; HU, Yufen; ZHANG, Hongxi; WANG, Peng; (42 pag.)WO2018/191238; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 29043-48-9, A common heterocyclic compound, 29043-48-9, name is 2-Methyl-1H-benzoimidazol-5-ylamine, molecular formula is C8H9N3, 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 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.

The synthetic route of 29043-48-9 has been constantly updated, and we look forward to future research findings.

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

Electric Literature of 144689-93-0, 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 144689-93-0 as follows.

Example 6:; (5-MethyI-2-oxo-l,3-dioxol-4-yI)methyl 5-(2-hydroxypropan-2-yl)-2-propyl-3-[[4-[2- (2H-tetrazoI-5-yl)phenyl]phenyl]methyl]imidazole-4-carboxylate (olmesartan medoxomil) (Ie); Step I: 5-(2-Hydroxypropan-2-yl)-2-propyl-3-[[4-[2-(N-(2-trimethylsilylethoxymethyl) tetrazol-5-yl)phenyl]phenyl]methyl]imidazole-4-ethylcarboxylate (Vd); 2-Propyl-5-[(l-hydroxy-l-methyl)ethyl]-3H-imidazole-4-ethylcarboxylate (0.808 g, 0.0033675 mol) was added to the two isomers (IVb) (1.5 g, 0.0033675 mol) and K2CO3 (0.558 g, 0.0040382 mol) in anhydrous DMF (10 mL) under N2 atmosphere. The mixture was stirred at room temperature for 17 hrs (TLC monitoring: cyclohexane/AcOEt 6:4). The mixture was partitioned between water and AcOEt. The organic layer was washed with water (3 times), dried over Na2SO4 and concentrated under reduced pressure to give a residue (1.8 g) that was purified by flash chromatography on silica (cyclohexane/AcOEt 6:4) to give the isomer (Vd1) (0.499 g) and the isomer (Vd2) (0.206 g) as oils. Yield: 35%. (Vd1) (isomer with lower elution time):1H-NMR (400 MHz, CDCl3, delta): -0.03 (s, 9H, Me3Si), 0.92 (t, J=8.2Hz, 2H, SiCH2CH2O), 0.96 (t, J=7.2Hz, 3H, CH2CH2CH3), 1.18 (t, J=7.2etaz, 3H, OCH2CHi), 1.64 (s, 6eta, CMe2), 1.67-1.76 (m, 2H5 CH2CH2CH3), 2.66 (t, J=7.6Hz, 2H, CH2CH2CH3), 3.66 (t, J=8.2Hz, 2H, SiCH2CH2O), 4.22 (q, J=7.2etaz, 2H, OCH2CH3), 5.44 (s, 2H, ArCH2N), 5.78 (s, 2H, OCH2N), 6.84-6.86 (m, 2H) 7.14-7.16 (m, 2H) 7.41-7.43 (m, IH) 7.46-7.56 (m, 2H) 7.84- 7.86 (m, IH) (aromatic protons).(Vd2) (isomer with higher elution time): 1H-NMR (400 MHz, CDCl3, delta): -0.10 (s, 9H, Me3Si), 0.70 (t, J=8.4Hz, 2H, SiCH2CH2O), 0.92 (t, J=7.4Hz, 3H, CH2CH2CH5), 1.13 (t, J=7.0etaz, .3eta, OCH2CH3), 1.60 (s, 6eta, CMe2), 1.62-1.71 (m, 2H, CH2CH2CH3), 2.58 (t, J=7.8Hz, 2H, CH2CH2CH3), 3.39 (t, J=8.4Hz, 2H, SiCH2CH2O), 4.17 (q, J=7.2etaz, 2H, OCH2CH3), 5.05 (s, 2H, ArCH2N), 5.38 (s, 2H, OCH2N), 6.81-6.83 (m, 2H) 7.05-7.07 (m, 2H) 7.49-7.52 (m, 2H) 7.55-7.57 (m, IH) 7.61- 7.65 (m, IH) (aromatic protons). Step II: 5-(2-Hydroxypropan-2-yl)-2-propyl-3-[[4-[2-(N-(2-trimethylsilylethoxymethyl) tetrazol-5-yl)phenyl]phenyl]methyl]imidazole-4-carboxylic acid (Ve i); A solution of NaOH (0.052 g, 0.001311 mol> in water (1 mL) was added to compound (VdO (0.262 g, 0.0004337 mol) in THF (1 mL). The mixture was stirred at room temperature for 23 hrs (TLC monitoring: CH2Cl2/MeOH/AcOH 85:10:5). HCl IN was added until pH 4 was reached. The mixture was extracted with AcOEt. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to give the compound (Vei) (0.261 g) as a white solid, m.p. 68-69C. Yield: 99%. 1H-NMR (400 MHz, CDCl3, delta): -0.05 (s, 9H, Me3Si), 0.86 (t, J-7.2Hz, 3H, CH2CH2CH3), 0.89 (t, J=8.1etaz, 2H, SiCH2CH2O), 1.54-1.60 (m, 2H, CH2CH2CH3) 1.67 (s, 6H, CMe2), 2.94 (t, J-7.2Hz, 2H, CH2CH2CH3), 3.65 (t, J=8.1Hz, 2H, SiCH2CH2O), 5.75 (s, 2eta, ArCH2N), 5.79 (s, 2H, OCH2N), 6.97-6.99 (m, 2H) 7.12-7.14 (m, 2H) 7.35-7.38 (m, IH) 7.44-7.53 (m, 2H) 7.83-7.85 (m, IH) (aromatic protons). Step III: 4-Bromomethyl-5-methyl~l,3-dioxol~2-one; A mixture of 4,5-dimethyl-l,3-dioxol-2-one (1.5 g, 0.013158 mol), NBS (2.34 g, 0.013158 mol) and benzoyl peroxide (0.089 g, 0.0003684 mol) in CCl4 (20 mL) was stirred at 77C for 6 hrs (TLC monitoring: cyclohexane/AcOEt 6:4). The solution was treated with an aqueous solution OfNaHCO3 and extracted with CH2Cl2. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to give 4-bromomethyl-5 -methyl- 1,3- dioxol-2-one (2.34 g). Yield: 92%.1H-NMR (400 MHz, CDCl3, delta): 2.13 (s, 3H, CH3), 4.18 (s, 2H, CH2Br). Stp IV: (5-Methyl-2-oxo-l,3-dioxol-4-yl)methyl 5-(2~hydroxypropan-2-yl)-2-propyl-3-[[4- [2-(N-(2-trimethylsilylethoxymethyl)tetrazol-5-yl)pherpsil]phenyl]methyl]imidazole-4- carboxylate (Vf1); A mixture of the compound (Ve1) (0.260 g, 0.0004516 mol), 4-bromomethyl-5-methyl-l,3- dioxol-2-one (0.1 g, 0.000518 mol) and K2CO3 (0.033 g, 0.000239 mol) in anhydrous DMF (1.5 mL) was stirred for 1.5 hrs at room temperature under N2 atmosphere (TLC monitoring: CH2Cl2/Me0H/Ac0H 85:10:5). The mixture was partitioned between a saturated solution of NaHCO3 and AcOEt. The organic phase was washed with water (3 times), dried over Na2SO4 and concentrated under reduced pressure to give the compound (Vf1) (0.3042g) as a yellow oil. Yield: 98%.1H-NMR (400 MHz, CDCl3, delta): -0.02 (s, 9H, Me3Si), 0.92 (t, J=8.1Hz, 2H, SiCH2CH2O), 0.98 (t, J=7.2Hz, 3H, CH2CH2CH3), 1.64 (s, 6eta, CMe2), 1.70-1.80 (m, 2H, CH2CH2CH3), 2.07 (s, 3H, CH3C=C), 2.76 (m, 2H, CH2CH2CH3), 3.67 (t, J=8.1Hz, 2H, SiCH2CH2O), 4.89 (s, 2eta, COOCH2), 5.41 (s, 2H, ArCH2N), 5.79 (s, 2H, OCH2N), 6.80-6.82 (m, 2H) 7.14-7.16 (m, 2H) 7.44-7.52 (m, 2H) 7.54-7.58 (m, IH) 7.85-7.87 (m, IH) (aromatic protons). Step V: (5-Methyl-2-oxo-l,3-dioxol-4-yl)methyl 5-(2-hydroxypropan-2-yl)~2~propyl~3-[[4- [2~(2H-tetrazol-5-yl)phenyl]phenyl]methyl]imidazole-4-carboxylate (olmesartan medo…

According to the analysis of related databases, 144689-93-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; S.I.M.S. S.r.l. – SOCIETA ITALIANA MEDICINALI SCANDICCI; WO2008/12852; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 46006-36-4, 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 46006-36-4 as follows.

3H-Benzoimidazole-4-carboxylic acid[3-(1H-tetrazol-5-yl)-phenyl]-amide (16) 3-(1H-Tetrazol-5-yl)aniline (75 mg, 0.47 mmol), 1H-benzimidazole-4-carboxylic acid (76 mg, 0.47 mmol), 1-ethyl-3-[3-dimethylaminopropyl]carbodiimide hydrochloride (135 mg, 0.7 mmol), 1-hydroxybenzotriazole (95 mg, 0.7 mmol) and N,N’-diisopropylethylamine (0.17 mL, 0.94 mmol) was stirred in DMF (0.5 mL) at room temperature for 24 h. The reaction mixture is diluted with water (2 mL) and after approximately adjusting the pH to 4 with 1N HCl, the mixture was extracted with ethyl acetate. The organic extracts were washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. The crude material was purified by reverse phase HPLC to afford the product as a trifluoroacetic acid salt in 5% yield. 1H NMR (DMSO-d6) delta 8.62 (s, 1H), 8.53 (s, 1H), 7.99-8.02 (m, 3H), 7.86 (d, J=8 Hz, 1H), 7.77 (d, J=4 Hz, 1H), 7.62 (t, J=8 Hz, 1H), 7.43 (t, J=8 Hz, 1H), 7.04 (s, 1H); LCMS (ESI) m/z 306 (MH+).

According to the analysis of related databases, 46006-36-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITY OF SOUTH FLORIDA; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; Chen, Yu; Nichols, Derek; Renslo, Adam R.; Jaishankar, Priyadarshini; Lauterwasser, Erica M. W.; (29 pag.)US9556131; (2017); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 2302-25-2, name is 4-Bromo-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 2302-25-2, Computed Properties of C3H3BrN2

(i) Production of (1H-Imidazol-4-yl)-(naphthalen-2-yl)ketone 4-Bromo-1H-imidazole (1.95 g) was dissolved in THF (30 ml), and the solution was cooled to -78 C. To the solution was added a solution of t-butyllithium in pentane (1.7 M; 20 ml). The mixture was stirred at 0 C. for 1.5 h. The mixture was again cooled to -78 C., and a solution of 2-formylnaphthalene (3.32 g) in THF (20 ml) was added. After the temperature was elevated from -78 C. to room temperature, the mixture was stirred at room temperature for 16 h. To the mixture was added an aqueous solution of ammonium chloride, and the mixture was extracted with ethyl acetate. The organic layer was dried and concentrated. The residue was purified by silica gel column chromatography,(eluent, dichloromethane_methanol=10:1). Recrystallization from dichloromethane-methanol gave the titled compound (1.00 g) as a colorless solid. 1H-NMR (CDCl3) delta: 7.53-7.70 (2H, m), 7.84-8.40 (6H, m), 8.53 (1H, s), 10.82 (1H, brs). IR (KBr): 2592, 1640, 1127, 779 cm-1.

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; Takeda Chemical Industries, Ltd.; US6573289; (2003); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem