Month: November 2020

96797-15-8,Some common heterocyclic compound, 96797-15-8, name is 4-Iodo-1-trityl-1H-imidazole, molecular formula is C22H17IN2, 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 solution of 4-IODO-1-TRITYL-LH-IMIDAZOLE (1 eq) in THF at room temperature was added ethylmagnesium bromide (1.2 eq) under dry conditions. After stirring for 90 minutes, zinc chloride (1.2 eq) was added to the reaction mixture. After stirring for another 90 minutes, tetrakis (triphenylphosphine) palladium (10%) and 5- bromopyrazine (1.3 eq) were added to the reaction mixture. Subsequent reaction conditions and work up are as described previously in Example 73, the resulting solid 2-(LH-IMIDAZOL-4-YL)-PYRAZINE (37%) was collected by filtration. MH (147)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Iodo-1-trityl-1H-imidazole, its application will become more common.

Reference:
Patent; CHIRON CORPORATION; WO2004/96822; (2004); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

693-98-1, 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. 693-98-1, name is 2-Methyl-1H-imidazole, A new synthetic method of this compound is introduced below.

General procedure: A mixture of aryl imidazoles (0.5 mmol), arylboronic acid (1 mmol), K2CO3 (1 mmol), C-1 complex (5 mol percent, 9.79 mg) in iso-propanol (1.5 mL) was stirred in a 50 mL oven dried round bottomed flask. After the completion of the reaction (monitored by TLC), the mixture was diluted with 20 mL water. The organic part was extracted with diethyl ether (3 20 mL) followed by drying over anhydrous Na2SO4, and the solvent was evaporated under reduced pressure to obtain the crude product. The residue was then purified with column chromatography using methanol/ethyl acetate (1:9) as eluent to afford the desired product.

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; Gogoi, Ankur; Sarmah, Gayatri; Dewan, Anindita; Bora, Utpal; Tetrahedron Letters; vol. 55; 1; (2014); p. 31 – 35;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A common heterocyclic compound, 10111-08-7, name is Imidazole-2-carboxaldehyde, molecular formula is C4H4N2O, 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. 10111-08-7.

Example 61;3H-Imidazole-2,4-dicarboxylic acid 2-amide 4-{ [2-(4,4-dimethyl-cyclohex-l-enyl)- phenyl] -amide}; a) 1 -(2-Trimethylsilanyl-ethoxymethyl)- lH-imidazole-2-carbaldehyde; A mixture of lH-imidazole-2-carbaldehyde (1.1 g, 11 mmol), potassium carbonate (3.0 g, 23 mmol), and SEM-Cl (2.4 mL, 14 mmol) in 10 mL of acetone was heated to 60 0C for 8 h. The mixture was diluted with EtOAc (100 mL) and washed with NaHCO3 (2 x 100 mL) and brine (100 mL) and the organic layer dried (Na2SO4) and concentrated. The title compound was purified by elution from a 20-g SPE column with 50 % EtOAc to give 1.5 g (58 %) of a colorless oil. 1H-NMR (CDCl3, 400 MHz): delta 9.82 (s, IH), 7.38 (d, J = 1.0 Hz, IH), 7.34 (d, J = 1.0 Hz, IH), 5.78 (s, 2H), 3.55 (m, 2H), 0.94 (m, 2H), -0.02 (s, 9H).

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

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2007/123516; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

60-56-0, A common heterocyclic compound, 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, molecular formula is C4H6N2S, 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.

Figure 1 shows the structures and synthetic pathways of methimazole derivatives. Briefly, compound 3 (3) was prepared through the reaction of an MMI (compound 2; 2) (400 mg, 3.5 mmol) and potassium carbonate (968 mg, 7 mmol) in 7 mL of N,N-dimethylformamide and the subsequently di-tert-butyl dicarbonate (1.1 mL, 5.2 mmol) was added. The reaction mixture was stirred at 60 C for 30 min in an N2 atmosphere. The resulting mixture was partitioned between ethyl acetate (40 mL) and H2O (20 mL). The organic layer was washed with brine (20 mL), dried over MgSO4, and then concentrated in vacuo. The residue was separated by chromatography over silica gel and eluted with hexane/ethyl acetate (1:1) to afford 665 mg (89% yield) of 3.

The synthetic route of 60-56-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chan, Chin-Feng; Lai, Shih-Ting; Guo, Yi-Cin; Chen, Ming-Jen; Bioorganic and Medicinal Chemistry; vol. 22; 9; (2014); p. 2809 – 2815;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 46006-36-4, name is 1H-Benzimidazole-7-carboxylic acid belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. 46006-36-4

1 H-Benzoimidazole-4-carboxylic acid (7.3 g) was suspended in 350 ml of tetrahydrofuran and cooled with dry ice-acetone bath. Lithium aluminium hydride (4M, 21 ml) was slowly added. The reaction wasstirred and allowed to warm up to room temperature overnight. The reaction was quenched with 5 ml methanol and extracted with 800 ml of 20% methanol and 80% ethyl acetate. After filtration, solid was discarded. Evaporation of filtrate under reduced pressure resulted in 7 g crude (1H-Benzoimidazol-4-yl)methanol (M+1=149.1,) to be used for next step

The synthetic route of 46006-36-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; ZHOU, Qun-Yong; (93 pag.)WO2017/177026; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

3034-50-2, 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. 3034-50-2, name is Imidazole-4-carbaldehyde, A new synthetic method of this compound is introduced below.

A 22-L, four-neck, round-bottom flask equipped with a mechanical stirrer, a temperature probe, a condenser, and an addition funnel with a nitrogen inlet was charged with 1H-imidazole-4-carboxaldehyde (Aldrich, 1.10 kg, 11.5 mol) and pyridine (3.0 L, 3.0 mol). The reaction flask was cooled to 8¡ã C. with an ice bath and hydroxylamine hydrochloride (871 g, 12.5 mol) was added slowly in portions to maintain the internal temperature below 30¡ã C. The reaction was allowed to cool to ambient temperature and stirred for 2 h at ambient temperature. The resulting thick yellow solution was heated to 80¡ã C. with a heating mantle and acetic anhydride (2.04 L, 21.6 mol) was added dropwise over 200 min to maintain the temperature below 110¡ã C. during the addition. The reaction mixture was heated at 100¡ã C. for 30 min, after which time it was allowed to cool to ambient temperature and then further cooled in an ice bath. The pH was adjusted to 8.0 (pH meter) by the addition of 25 wt percent NaOH (5.5 L) at such a rate that the internal temperature was maintained below 30¡ã C. The reaction mixture was then transferred into a 22-L separatory funnel and extracted with ethyl acetate (6.0 L). The combined organic layer was washed with brine (2.x.4.0 L), dried over MgSO4, filtered, and concentrated to dryness under reduced pressure at 35¡ã C. to give the crude product as a yellow semisolid. The resulting semisolid was suspended in toluene (3.0 L) and stirred for 1 h, after which time it was filtered to give a light yellow solid, which was resuspended in toluene (3.0 L) and stirred for 1 h. The resulting slurry was filtered and the filter cake washed with toluene (2.x.500 mL) to give the title compound as a light yellow solid [870 g, 82percent). The 1H and 13C NMR spectra were consistent with the assigned structure.

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; Baumann, Christian Andrew; Gaul, Michael David; Johnson, Dana L.; Tuman, Robert W.; US2006/281788; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 1849-01-0 name is 1-Methyl-1H-benzo[d]imidazol-2(3H)-one, 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. 1849-01-0

Example 7 Preparation of 1,3-dihydro-1-methyl-3-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-2H-benzimidazol-2-one (Compound 159) A mixture of 3-[4-(chloromethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (i.e. the product of Example 1, Step B) (0.3 g, 1.1 mmol), 1,3-dihydro-1-methyl-2H-benzimidazol-2-one (0.17 g, 1.1 mmol) and cesium carbonate (0.56 g, 1.7 mmol) in N,N-dimethylformamide (2.5 ml) was stirred at room temperature for 12 h. The reaction mixture was partitioned between ethyl acetate (25 ml) and water (5 ml). The organic layer was separated and washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting material was purified by silica gel chromatography (eluting with a gradient of 0 to 50% ethyl acetate in hexanes) to provide the title compound, a compound of the present invention, as a solid (0.095 g). 1H NMR (CDCl3): delta 3.49 (s, 3H), 5.16 (s, 2H), 6.81-6.90 (m, 1H), 6.97-7.06 (m, 2H), 7.06-7.18 (m, 1H), 7.47 (d, 2H), 8.07 (d, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Methyl-1H-benzo[d]imidazol-2(3H)-one, and friends who are interested can also refer to it.

Reference:
Patent; FMC Corporation; PASTERIS, Robert James; CHITTABOINA, Srinivas; MCMAHON, Travis Chandler; KAMIREDDY, Balreddy; REDDY, Ravisekhara Pochimireddy; (121 pag.)US2020/148672; (2020); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

2849-93-6, 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. 2849-93-6, name is 1H-Benzimidazole-2-carboxylic acid, A new synthetic method of this compound is introduced below.

To awarm solution of [(eta6-p-cymene)RuI2]2 (49 mg, 0.05 mmol)in ethanol (2.5 mL) a warm solution of HL (16 mg, 0.1 mmol) inethanol (2.5 mL) and triethylamine (13.92 mL), were added. Themixture was stirred at room temperature for 4 h. The orange-redproduct was filtered off, washed with ethanol (4 mL), diethylether and dried in vacuo. Yield: 35.7 mg, 68.4%. Anal. Calcd forC18H19IN2O2Ru, %: C, 41.31; H, 3.66; N, 5.35. Found, %: C, 41.27; H,3.75; N, 5.22. IR (ATR, cm1): 3070(m), 2962(s), 2754(m), 1637(s),1590(m), 1527(s), 1474(s), 1329(s), 1228(m). 1H NMR (199.97 MHz,DMSO-d6, delta, ppm): 14.06 (s, 1H, NH), 7.98 (dd, 1H, JHeH 2.7 and6.5, Hz, CHL), 7.63e7.56 (m, 1H, CHL), 7.55e7.45 (m, 2H, CHL), 5.99(d, 1H, JHeH 5.9 Hz, CHcymene), 5.90 (q, 2H, JHeH 6.3 Hz, CHcymene),5.80 (d, 1H, JHeH 5.9 Hz, CHcymene), 2.81 (m, 1H,JHeH 6.9 Hz, eCH(CH3)2), 2.33 (s, 3H,eCH3), 1.14 (dd, 6H,JHeH 2.8 and 6.9 Hz, eCH(CH3)2). 13C NMR (50.28 MHz, DMSO-d6 ,delta, ppm): 20.27 (eCH3), 22.15 (eCH(CH3)2), 31.55 (eCH(CH3)2),79.05, 80.18, 80.88, 81.08, 86.17 (CHcymene), 96.76 (CeCH3), 103.30(CeCH(CH3)2), 114.12, 118.40, 124.42, 125.69 (CHL), 134.02, 140.90(CeCHL), 145.11 (CeCOO), 163.65 (eCOO). ESI-MS (MeOH): m/z397.049 [M-I]+, 353.059 [M-I-CO2]+.

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; Panti?, Darko N.; Arancrossed D Signelovi?, Sandra; Radulovi?, Sini?a; Roller, Alexander; Arion, Vladimir B.; Grguri?-?ipka, Sanja; Journal of Organometallic Chemistry; vol. 819; (2016); p. 61 – 68;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

60-56-0, Adding some certain compound to certain chemical reactions, such as: 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, 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 60-56-0.

To 10 mL of Acetonitrile were added 3 mmol (1.05 g) of methyl 4-chloro-3-[(E)- dimethylaminomethyleneamino]sulfonyl-5-nitro-benzoate (WO 2012/018635) 3.3 mmol (376 mg) of 2-mercapto-1-methylimidazole and 6.6 mmol (910 mg) of K2C03. The solution was stirred at room temperature overnight. When TLC showed no remaining methyl 4-chloro-3-[(E)- dimethylaminomethyleneamino]sulfonyl-5-nitro-benzoate the reaction mixture was diluted with 10 mL of water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried with Na2S04 and evaporated under reduced pressure. The crude product was then purified by recrystallization from ethanol to yield 1.04 g of yellow crystals (81 % yield). 1H NMR (200 MHz, DMSO-cf6) d 8.66 (d, J = 1.9 Hz, 1 H), d 8.34 (d, J = 1.8 Hz, 2H), d 7.28 (s, 1 H), d 6.87 (s, 1 H), d 3.91 (s, 3H), 3.51 (s, 3H), d 3.10 (s, 3H), d 2.92 (s, 3H). MS m/z: not found

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 60-56-0.

Reference:
Patent; UNIVERSITAeT WIEN; ERKER, Thomas; SCHREPPEL, Philipp; (235 pag.)WO2019/193159; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

57090-88-7, 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. 57090-88-7, name is 1H-Imidazole-4-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows.

Step 1: 1-((6-(trifluoromethyl)pyridin-3-yl)methyl)-1H-imidazole-4-carbonitrile 1H-imidazole-4-carbonitrile (300 mg, 3.22 mmol) and chloromethyl)-2-(trifluoromethyl)pyridine (662 mg, 3.385 mmol) were taken into anhydrous DMF (5 ml) and cooled to 0 C. Sodium hydride (150 mg, 3.72 mmol) was added to the mixture portionwise then warmed to room temperature. After stirring for 2 hours, the reaction was quenched with saturated ammonium chloride (10 ml). The mixture was diluted with dichloromethane (25 ml) and water (20 ml) and the layers separated. The aqueous was extracted with dichloromethane (2*10 ml). The combined organic extracts was washed with water (10 ml) and brine (2*10 ml), dried over anhydrous sodium sulfate, filtered, and evaporated in vacuo. The crude product was purified by column chromatography (SiO2) eluting with to provide a white solid (79 mg, 9.7% yield). 1 H NMR (300 MHz, CDCl3) delta H NMR (300 MHz, (m, 1H), 8.79-8.57 (m, 1H), 8.50-8.23 (m, 1H), 8.02-7.83 (m, 2H), 7.84-7.72 (m, 1H), 5.56 (s, 2H).

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; Vertex Pharmaceuticals Incorporated; Lauffer, David J.; Bemis, Guy; Boyd, Michael; Deininger, David; Deng, Hongbo; Dorsch, Warren; Gu, Wenxin; Hoover, Russell R.; Johnson, JR., Mac Arthur; Ledeboer, Mark Willem; Ledford, Brian; Maltais, Francois; Penney, Marina; Takemoto, Darin; Waal, Nathan D.; Weng, Tiansheng; (667 pag.)US2019/322673; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem