Category: imidazoles-derivatives

Reference of 41716-18-1,Some common heterocyclic compound, 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, molecular formula is C5H6N2O2, 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.

The complex 1 was obtained during attempted 1:2CuSO4.5H2O and L1H in methanol/water (2:1 v/v) solution atroom temperature under continuous stirring. After stirring for20 min, the solution that resulted from the mixture was filteredoff and allowed to evaporate at room temperature. Blue blockcrystals of 1 formed in about 5 days. Elemental analysis for 1,Anal. Calcd. (percent): C, 31.13; H, 4.70; N, 14.52. Found: C, 31.17;H, 4.73; N, 14.59.

The synthetic route of 41716-18-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yang, Li-Jing; Song, Wen-Tao; Luo, Yang-Hui; Sun, Bai-Wang; Inorganic and Nano-Metal Chemistry; vol. 47; 4; (2017); p. 493 – 499;,
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. 934-32-7, name is 1H-Benzo[d]imidazol-2-amine, A new synthetic method of this compound is introduced below., SDS of cas: 934-32-7

General procedure: A mixture of ethyl acetoacetate and/or acetylacetone (1 mmol) or malononitrile(1.1 mmol), 2-aminobenzimidazole (1 mmol), aldehyde (1 mmol) and [PVPH]ClO (30 mg, 6.84 mol %) was heated at 100 C in an oil bath for the appropriate time.After completion of the reaction [monitored by thin layer chromatography (TLC): nhexane:ethyl acetate (3:1)], the reaction mixture was cooled to room temperatureand EtOH (5 mL) was added to it and filtered to separate the catalyst. Afterevaporation of the solvent from the filtrate, the crude solid product wasrecrystallized from ethanol to obtain pure A or B products.The spectral [IR, proton ( 1H) NMR and 13C NMR] data of new compounds arepresented below.

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; Abedini, Masoumeh; Shirini, Farhad; Mousapour, Maryam; Goli Jolodar, Omid; Research on Chemical Intermediates; vol. 42; 7; (2016); p. 6221 – 6229;,
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. 37148-86-0, name is 4-(4-(Trifluoromethyl)phenyl)-1H-imidazole, A new synthetic method of this compound is introduced below., Application In Synthesis of 4-(4-(Trifluoromethyl)phenyl)-1H-imidazole

Example 11 : Preparation of 4-[4-(4-trifluoromethylphenyl)-lH-imidazol-l-yl]-benzonitrile.4-Trifluoromethylphenyl imidazole (4.0 g, 19 mmol), 4-fluorobenzonitrile (1.2 g, 8.5 mmol) and potassium carbonate (1.5 g, 10.9 mmol) were combined in DMSO (15 mL) and heated at 100 0C for 6 h. The cooled solution was then poured onto water (100 mL), and the resulting solid was filtered and air-dried to give the imidazole nitrile (4.65 g) as a white solid: mp 252 0C; 1H NMR (300 MHz, CDCl3) delta 8.05 (s, IH), 7.95 (d, J= 8 Hz, 2H), 7.85 (d, 2 H), 7.72 (s, IH), 7.72 (d, J= 8 Hz, 2 H), 7.62 (d, J= 8 Hz, 2H); ESIMS m/z 314.1 (M+H). Anal. Calcd. for Ci6Hi0F3N3O2: C, 65.18; H, 3.22; N, 13.41. Found: C, 64.49; H, 3.23; N, 13.08.

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; DOW AGROSCIENCES LLC; LAMBERT, William; CROUSE, Gary; SPARKS, Thomas; CUDWORTH, Denise; WO2011/17513; (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 75370-65-9 as follows. Safety of 4-Amino-1H-benzo[d]imidazol-2(3H)-one

Amine 2a (1.3 g, 5.9 mmol) was dissolved in 40 ml of AcOEt and at 0C triphosgene (1.75 g, 5.9 mmol) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 5ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound la (860 mg, 5.77 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt). The solvent was evaporated and the crude was dissolved in AcOEt (50 ml) and washed with water (1 X 30 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 650mg of a yellow solid. Yield = 28% ‘HNMR (DMSO, 200 MHz) delta 2.51 (6H, bs), 4.43 (2H, d, J = 5.6 Hz), 6.62 (1H, dd, J = 7.6 Hz, J’ = 1 Hz), 6.82 (2H, m), 6.97 (1H, dd, J = 8 Hz, J’ = 1 Hz), 7.32 (1H, s), 7.39 (1H, d), 7.49 (1H, d), 8.35 (1H, bs), 9.99 (1H, bs), 10.59 (1H, bs); [M+1] 394.1 (C18H18F3N5O2 requires 393.36).

According to the analysis of related databases, 75370-65-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PHARMESTE S.R.L.; NAPOLETANO, Mauro; TREVISANI, Marcello; PAVANI, Maria Giovanna; FRUTTAROLO, Francesca; WO2011/120604; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 28890-99-5, A common heterocyclic compound, 28890-99-5, name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, molecular formula is C13H9N3, 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.

Compound 4-1 (3 g, 5.8 mmol), benzimidazolo[1,2-a]benzimidazole (1.26 g, 6.1 mmol), and potassium phosphate (2.58 g, 12.2 mmol) were suspended in NMP (29 mL). The mixture was stirred at 190 Cfor48 h. After the reaction mixture was cooled at room temperature, 58 mL of EtCH and 29 mL of water were added to the reaction mixture to give a solid. Itwas collected by filtration, and it was purifed by column chromatography on silica gel eluting with a mixed solvent of toluene and CHCI3. Then, the product was recrystallized with toluene and heptane. The formed solid was collected by filtration and dried in vacuum to yield 2.39 g (59%) of compound (B-25) as a white solid. LC-MS (mlz) 704.1HNMR (300 MHz, DMSC-d6): 68.39-8.36 (m, 2H), 8.15-8.12 (m,1H), 8.01-7.72 (m, 9H),7.61-7.25 (m, 13H), 7.01(d, J= 1.4 Hz, 1H), 7.54 (td, J= 7.5, 1.2 Hz, 1H), 6.57 (td, J= 7.5,1.2 Hz, 1H)

The synthetic route of 28890-99-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IDEMITSU KOSAN CO., LTD.; NISHIMAE, Yuichi; KOHLSTEDT, Julia; SCHAeFER, Thomas; NAGASHIMA, Hideaki; (114 pag.)WO2016/97983; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 17325-26-7, These common heterocyclic compound, 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, 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) Methyl 2-isopropyl- lH-imidazole-4-carboxylateA solution of methyl lH-imidazole-4-carboxylate (5.0 g, 39.68 mmol), AgN03 (4.0 g, 23.81 mmol), isobutyric acid (10.4 g, 1 19.1 mmol) in 10 % H2S04 (150 ml) was heated at 80 C for 15 min. An aqueous solution of (NH4)2S208 (28.0 g, 119.1 mmol) was added to the mixture dropwise in 15 minat 80 C. The reaction mixture was cooled to RT and poured into ice. The mixture was basified with aqueous ammonia (pH 9) and extracted with EtOAc (500 ml). The organic layer was concentrated and the residue was purified by flash chromatography. Yield 1.5 g. 1H- NMR (400 MHz; CDC13): delta 1.36 (d, 6H), 3.05-3.14 (m, 1H), 3.87 (s, 3H), 7.62 (s, 1H).

The synthetic route of 17325-26-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ORION CORPORATION; TOeRMAeKANGAS, Olli; WOHLFAHRT, Gerd; SALO, Harri; RAMASUBRAMANIAN, Rathna, Durga; PATRA, Pranab, Kumar; MARTIN, Arputharaj, Ebenezer; HEIKKINEN, Terhi; VESALAINEN, Anniina; MOILANEN, Anu; KARJALAINEN, Arja; WO2012/143599; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 1003-21-0, 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 1003-21-0 as follows.

Example 14a: 4-((3-(4-(1H-1,2,4-triazol-1-yl)benzyl)-4-chloro-2-methoxyquinolin-6-yl)(hydroxy)(1-methyl-1H-imidazol-5-yl)methyl)benzonitrile A solution of isopropylmagnesium chloride-lithium chloride complex in tetrahydrofuran (1.3 M, 0.986 mL, 1 ,28 mmol) was added dropwise to an ice-water cooled, stirring suspension of 5- bronio-1 -methyl- IH- imidazole (241 mg, 1.50 mmol) in dry tetrahydrofuran (6 mL). After 5 minutes, the flask was removed from the cooling bath and the white suspension was stirred at 23 C. After 10 minutes, the Grignard suspension was added to an ice-water cooled, stirring mixture containing 4-(3-(4-( IH- 1 ,2,4-triazol- 1 -yl)benzyl)-4-chloro-2-methoxyquinoline-6- carbonyl)benzonitrile (205 mg, 0.427 mmol, Intermediate 16: step e) and lanthanum(III) chloride bis(lithium chloride) complex (0.6 M solution in tetrahydrofuran, 1.42 mL, 0.854 mmol) in dry tetrahydrofuran (8 mL), After 20 minutes, 1 M aqueous citric acid solution (1 niL) was added. The flask was removed from, the cooling bath and then ethyl acetate (100 mL) was added. Additional 1 M aqueous citric acid solution (-15 mL) was added until the mixture was comprised of two homogeneous layers, at which point saturated aqueous sodium bicarbonate solution was added until the H of the aqueous layer was ~8 by litmus paper test. The layers were separated. The aqueous layer was extracted with ethyl acetate (20 mL). The organic layers were combined and the combined solution was dried over sodium sulfate. The dried solution was filtered. Silica gel (5 g) was added to the filtrate and the mixture was concentrated by rotary evaporation to afford a free-flowing powder. The powder was loaded onto a silica gel column for flash-column chromatography purification. Elution with dichloromethane initially, grading to 50% methanol–dich.lorometh.ane provided the title compound as a w hite solid. H NMR (5001 MHz, CDCI3) delta ppm 8.45 (s, 1H), 8.10 (d . ./ 2.2 Hz, 1 I S). 8.0(S (s, U S). 7.81 (d, ,/ 8.8 Hz, 1H), 7.65 (d, J = 8.5 Hz, 2H), 7.58-7.51 (m, 5H), 7.44-7.38 (m, 3H), 6.41 (d, ,7 = 1.1 Hz, 1H), 4.33 (s, 2H), 4.09 (s, 3H), 3.94 (s, 1H), 3.38 (s, 3H); MS (ESI): mass calcd. C31H24CIN7O2, 561.2; m/z found, 562.1 [M+H]+.4-((3-(4-(l H-l ,2,4-Triazol-l-yl)benzyl)-4-chloro-2-methoxyquinolin-6lH-imidazol-5-yl)methyl)benzonitrile was purified by chiral SFC (Chiralpak AD-H column, 5 mupiiota, 250 mm. 20 mm, mobile phase: 60% C02, 40% methanol) to give two enantiomers. The first eluting enantiomer was Example 14b:3H NMR (500 MHz, CDCI3) delta ppm 8.44 (d, J = 1.0 Hz, 1H), 8.10 (d, J= 2.1 Hz, 1 H), 8.06 (s, 1 H), 7.81 (d, J= 8.7 Hz, 1H), 7.66 (d, J= 8.2 Hz, 2H), 7.58-7.50 (m, 5H), 7.44-7.38 (m, 3H), 6.42 (s, 1H), 4.33 (s, 2H), 4,09 (s, 3H), 4.02-3.81 (br s, 1 H), 3.38 (s, 3H); MS (ESI): mass calcd. C31H24CIN7O2, 561.2; m/z found, 562.3 [M+H]+ and the second eluting enantiomer was Example 14c: H NMR (500 MHz, CDCI3) delta ppm. 8.45 (s, I I I). 8.09 (d, J —— 2.2 Hz, 1 H), 8.06 (s, IH), 7.85 (d, ./ 8.9 Hz, 1H), 7.66 (d, ./ = 8.1 Hz, 21 1).7.58-7.51 (m, 5H), 7.45-7.38 (m, 3H), 6.43 (s, 5 H), 4.33 (s, 2H), 4.09 (s, 3H), 3.38 (s, 3H); MS (ESI): mass calcd. C31H24CIN7O2, 561 .2; m/z found, 562.3 [M+H]+.

According to the analysis of related databases, 1003-21-0, the application of this compound in the production field has become more and more popular.

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

Electric Literature of 144689-93-0, A common heterocyclic compound, 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, molecular formula is C12H20N2O3, 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.

EXAMPLE 2: 3-(4-Bromo-benzyl)-5-(1-hydroxy-1-methyl-ethyl)-2-propyl-3H-imidazol-4-carboxylic acid ethyl ester (IV; X=Br) A mixture of a compound of formula (IX), in which R4 is ethyl (100 g, 0.417 mol), a compound of formula (X), in which X=Z=Br (107.5 g, 1.03 mol) and K2CO3 (71 g, 0.516 mol) in DMA (400 mL) is reacted at room temperature, under stirring, for 18 hours. The reaction mixture is then diluted with water and the precipitated solid is filtered and dried in a static dryer under vacuum. 152 g of the title compound are obtained; yield: 89%.

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; Dipharma Francis S.r.l.; EP1905770; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

496-46-8, name is Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. category: imidazoles-derivatives

Preparation of a cucurbituril trimer (Figure 23, Compound 38) :; As is exemplified in Figure 23, an exemplary pathway for forming a cucurbituril trimer involves a disubstituted cucurbituril derived from benzil. Such a pathway generally includes preparation of a benzil-derived glycoluril, as described hereinabove, a formation OF A DERIVATIZED CB monomer, and a trimerization step. As a starting material, a benzil-derived glycoluril (Figure 23, Compound 35) is prepared by reacting a para-substituted benzil with urea in a 1: 2 ratio in benzene and trifluoroacetic acid, according to the exemplary syntheses are presented hereinabove. In one non-limiting example, one of the para-substituents on the benzil is a carboxyl group and the second is hydrogen (Figure 23, Compound 34). Compound 35, is reacted with glycoluril, Compound 2, in a 1: 5 ratio, and with formaldehyde, in the presence of concentrated sulfuric acid, to thereby form the derivatized cucurbituril biphenyl-CB [6] (Figure 23, Compound 36). Compound 36 is reacted with 1,3, 5-benzenetriamine (BTA) in a 3: 1 ratio so as to form three amide bonds between each of the carboxyl groups on the derivatized CB [6] and an amine on the BTA, and thus form a cucurbituril trimer having a BTA as the assembling unit (Figure 23, Compound 38).

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

Reference:
Patent; TECHNION RESEARCH & DEVELOPMENT FOUNDATION LTD.; WO2005/23816; (2005); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 288-32-4, name is 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 288-32-4, Application In Synthesis of 1H-Imidazole

General procedure: Arylhalide (1.0 mM), nitrogen-containing heterocycle (1.2 mM), KOH (2 mM), and the catalyst (0.75 M%) were stirred in dimethyl sulfoxide (DMSO) (4 mL) at 110 C for 10 h. After completion of the reaction, the mixture was cooled to room temperature, diluted with ethyl acetate (10 mL) and filtered. The filtrate was concentrated and the residue was purified by column chromatography on silica gel using hexane/ethyl acetate(70 : 30) as eluent to afford the desired product. The products have been characterized by 1H NMR spectroscopy.

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; Anitha, Panneerselvam; Manikandan, Rajendran; Viswanathamurthi, Periasamy; Journal of Coordination Chemistry; vol. 68; 19; (2015); p. 3537 – 3550;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem