Category: 16042-25-4

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. 16042-25-4, name is 2-Imidazolecarboxylic acid, A new synthetic method of this compound is introduced below., HPLC of Formula: C4H4N2O2

60 g of N,N-dimethylformamide as a solvent and Zn(OAc)2 and benzimidazole in a molar ratio of 1:1.5 were placed in a flask. The reaction was allowed to proceed at 130 C. for 24 h. The resulting solid was collected by filtration. The solid was precipitated in N,N-dimethylformamide, collected, and dried under vacuum at 180 C. for 3 h to afford Zn(benzimidazole)1.6(OAc)0.4 as a zinc-imidazole complex mixed catalyst. The catalyst was analyzed by Fourier-transform infrared (IR) spectroscopy and X-ray diffraction (XRD) and the results are shown in FIGS. 1-3.

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; KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY; LEE, Hyun Joo; Jae, Jungho; Kim, Hong Gon; Dahnum, Deliana; Cho, Shinhye; (14 pag.)US2020/61596; (2020); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 16042-25-4,Some common heterocyclic compound, 16042-25-4, name is 2-Imidazolecarboxylic acid, molecular formula is C4H4N2O2, 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 suspension of 0.351 g of imidazole-2-carboxylic acid (3.13 mmol) in 15 ml DMF were added 0.508 g of CDI (3.13 mmol) and 0.43 ml triethylamine (3.13 mmol), and the mixture stirred at ambient temperature for 1 h. Then the mixture was refluxed for 30 min. After cooling to ambient temperature, 0.5 g of 2-methoxy-5-(tetrahydro-pyran-4-yl)-phenylamine (2.4 mmol) was added and the reaction mixture was heated to reflux for 16 h. The mixture was evaporated and the residue taken up in water (40 ml) and extracted 3 times with methylene chloride. The combined organic phases were tried on sodium carbonate, evaporated and the residue was stirred in hot ethyl acetate. After filtration and trying 0.42 g 1H-Imidazole-2-carboxylic acid [2-methoxy-5-(tetrahydro-pyran-4-yl)-phenyl]-amide (57%) were obtained as a yellow solid; M.p.: 227-228 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Imidazolecarboxylic acid, its application will become more common.

Reference:
Patent; Flohr, Alexander; Jakob-Roetne, Roland; Norcross, Roger David; Riemer, Claus; US2004/229862; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 16042-25-4, A common heterocyclic compound, 16042-25-4, name is 2-Imidazolecarboxylic acid, molecular formula is C4H4N2O2, 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.

To a stirred suspension of 1H-imidazole-2-carboxylic acid (3.00 g, 26.8 mmol) in anh. DCM (45 mL)cooled to 0 C under N2 was added oxalyl chloride (4.5 mL, 53.5 mmol) followed by addition of DMF (2 drops). The reaction was allowed to warm to rt and stir overnight. A further portion of oxalylchloride (1.13 mL, 13.4 mmol) and DMF (1 drop) was added and the reaction stirred for 4 hr.Volatiles were then removed in vacuo and the residual oxalyl chloride was removed by coevaporationwith toluene to afford acid chloride as a colourless solid. The solid was then addedportionwise to conc NH4OH (15 mL) chilled to 0 C. Volatiles were then removed in vacuo.Residual volatiles were coevaporated with toluene to obtain dry material (25: 75 startingmaterial:product). The crude was retreated to the reaction with oxalyl chloride (1.7 mL, 20.1 mmol)using the above procedure. The solid obtained was then washed with water (2 x 20 mL) and driedin vacuo to obtain a tan solid (2.16 g, 73%) that was used without further purification. LCMS (Waters Atlantis: Gradient Method 2): Rt = 1.44 min, 99 A% 254 nm, [M + H]+ = 112.2. 1H NMR(600 MHz, DMSO-d6) delta 12.95 (s, 1H), 7.73 (s, 4H), 7.43 (s, 1H), 7.23 (br s, 1H), 7.04 (br s, 1H).

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; Jarrad; Debnath; Miyamoto; Hansford; Pelingon; Butler; Bains; Karoli; Blaskovich; Eckmann; Cooper; European Journal of Medicinal Chemistry; vol. 120; (2016); p. 353 – 362;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 16042-25-4, name is 2-Imidazolecarboxylic acid, 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 16042-25-4, name: 2-Imidazolecarboxylic acid

General procedure: Ligand 1 was prepared by refluxing equimolar solution of imidazole- 2-carboxylic acid (0.112 g; 1 mM) and benzhydrazide (0.136 g; 1 mM) (HL1) in 50 mL of methanol. After 24 h, the reaction mixture was cooled to room temperature and the product formed was filtered, washed several times with water and then recrystallized from methanol to afford the desired product in pure form. Other Ligands 2-4 (HL2-HL4) were also prepared by adopting the similar procedure as in the caset of ligand, using the respective hydrazides i.e., isonicotinic acid hydrazide (0.137 g; 1 mM), furoic acid hydrazide (0.126 g; 1 mM) and thiophene-2-carboxylic acid hydrazide (0.142 g; 1 mM as summarized in Scheme 1.

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-Imidazolecarboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sathyadevi, Palanisamy; Krishnamoorthy, Paramasivam; Butorac, Rachel R.; Cowley, Alan H.; Dharmaraj, Nallasamy; Inorganica Chimica Acta; vol. 409; PART B; (2014); p. 185 – 194;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 16042-25-4, name is 2-Imidazolecarboxylic acid, 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 16042-25-4, Product Details of 16042-25-4

General procedure: The syntheses of 1-5 followed a similar procedure. In thesynthesis of 1, CoCl2*2H2O (0.0129 g, 0.100 mmol) and 2-Htza(0.0129 g, 0.100 mmol) were dissolved in distilled water(5.0 ml). The solution was left undisturbed at room temperaturefor several days, from which 1 crystallized. The sameprocedure was adopted for the syntheses of 2 and 3, exceptthat NiCl2*2H2O (0.0129 g, 0.100 mmol) and Cd(NO3)2*4H2O(0.0129 g, 0.100 mmol), respectively, were used instead ofCoCl2*2H2O. The procedure was also applied for the preparationof 4 and 5, except that Co(NO3)2*6H2O (0.0290 g,0.100 mmol) was used as a metal salt, whereas 2-H2ima(0.0112 g, 0.100 mmol) and 4-Hoxa (0.0113 g, 0.100 mmol)were used as the ligands for the preparation of 4 and 5,respectively.

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 of 16042-25-4, These common heterocyclic compound, 16042-25-4, name is 2-Imidazolecarboxylic acid, 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.

PREPARATION 35 1-amino-N-o-tolyl-1H-imidazole-2-carboxamide a) N-o-tolyl-1H-imidazole-2-carboxamide To a solution of 1H-imidazole-2-carboxylic acid (0.52 g, 4.64 mmol) in DMF (20 mL) was added o-toluidine (0.50 mL, 4.64 mmol), EDC·HCl (1.35 g, 6.96 mmol) and HOBt (0.94 g, 6.96 mmol). The reaction mixture was stirred at room temperature for 16 hours. Then, it was poured into water and extracted with ethyl acetate. The combined organic layer was dried over sodium sulphate, filtered and concentrated to dryness. The crude product was purified by flash chromatography (2% to 3% MeOH/DCM) to yield 0.93 g (99%) of the title compound as a beige solid. LRMS (m/z): 202 (M+1)+.

Statistics shows that 2-Imidazolecarboxylic acid is playing an increasingly important role. we look forward to future research findings about 16042-25-4.

Reference of 16042-25-4, 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 16042-25-4 as follows.

A mixture of 3-(N-hydroxycarbamidoyl)-piperidine-l -carboxylic acid tert-butyl ester (0.25 g, 1.03 mmol, prepared as described in Example 5 (C)), lH-imidazole-2- carboxylic acid (116 mg, 1.03 mmol), HOBT (161 mg, 1.05 mmol), EDCLHCl (0.3 g, 1.55 mmol) and dry triethylamine (0.29 mL, 2.05 mmol) in dry DCM (10 mL) was stirred for 4h at ambient temperature, under nitrogen atmosphere. The solution was then concentrated under vacuum and the crude was purified on silica gel (eluent: DCM: MeOH 20:1) to afford 100 mg of 3-{[(hydroxyimino]-[(lH-imidazole-2- carbonyl)-amino] -methyl }-piperidine-l -carboxylic acid tert-butyl ester (yield: 29%; LCMS (RT): 2.54 min (Method B); MS (ES+) gave m/z: 357.95 (MH+).).A solution of 3-{[(hydroxyimino]-[(lH-imidazole-2-carbonyl)-amino]- methyl}-piperidine-l-carboxylic acid tert-butyl ester (0.1 g, 0.3 mmol) and DIEA (0.043 mL, 0.3 mmol) in MeCN (4 mL) was heated for 30 min at 150 in a sealed tube under microwave irradiation. Upon cooling a white solid precipitated which was collected by filtration to afford 43 mg of the title compound.Yield: 45% (white solid); LCMS (RT): 2.97 min (Method B); MS (ES+) gave m/z: 320.1 (MH+). EPO 17(B) 3-[5-(lH-imidazol-2-yl)-[l,2,4]oxadiazol-3-yl]-rhoiperidine trifluoroacetate.

According to the analysis of related databases, 16042-25-4, the application of this compound in the production field has become more and more popular.

Adding a certain compound to certain chemical reactions, such as: 16042-25-4, name is 2-Imidazolecarboxylic acid, 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 16042-25-4, Quality Control of 2-Imidazolecarboxylic acid

N-((3R,11R,E)-5,12-dioxo-3-phenyl-1-oxa-4-azacyclododec-8-en-11-yl)-1H-imidazole-2-carboxamide Under nitrogen, 1H-imidazole-2-carboxylic acid (8.40 mg, 0.075 mmol) was dissolved in anhydrous DMF (1.2 ml) with (iPr)2EtN (48.0 mul, 0.277 mmol). Next, the TFA salt form of (3R,11R,E)-11-amino-3-phenyl-1-oxa-4-azacyclododec-8 ene-5,12-dione (30.0 mg, 0.075 mmol), 1-hydroxybenzotriazole (15.93 mg, 0.104 mmol) and 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide (19.95 mg, 0.104 mmol) were added. The reaction mixture was stirred overnight (15 hours). Upon completion of the reaction, the reaction was diluted with EtOAc. The crude mixture was washed twice with saturated NH4Cl (*2), the half-saturated NaHCO3, and brine. The crude mixture was dried over Na2SO4 and concentrated under vacuum to yield a white wax. The product (23.8 mg) was isolated via silica chromatography using an ISCO automated system (MeOH/DCM gradient) in 90% yield in the form of a white solid. LRMS (ESI+) (M+H): 383.17

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Imidazolecarboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Buhrlage, Sara; Dockendorff, Chris; Foley, Mike; Kim, Han-Je; Germain, Andrew; MacPherson, Lawrence; Nag, Partha; Schreiber, Stuart; Ting, Amal; Weiwer, Michel; Youngsaye, Willmen; US2014/94462; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 16042-25-4,Some common heterocyclic compound, 16042-25-4, name is 2-Imidazolecarboxylic acid, molecular formula is C4H4N2O2, 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.

Synthesis of tert-butyi 4-(4-carbamoyl-4-(methylamino)piperidin-1~yl)~ 3-( 1 H-imidazote-2-carboxamido)phenylcarbamate (lnt-14b)A mixture of 1 H-imidazole-2-carboxylic acid (19 mg, 0.17 mmol), aniline lnt-14b (60 mg, 0.17 mmol), HATU (69 mg, 0.18 mmol), diisopropyiethylamine (57 pL, 0.33 mmol) was stirred in N,N-dimethylformamide (2 mL). Water and ethyl acetate were added, and the layers were separated. The separated organic layer was washed with water. The separated organic layer was dried ( gS04) and filtered. The solvents were removed in vacuo and chromatographic purification (ethyl acetate – hexane) of the residue gave amide lnt-14c (26 mg, 35%) as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Imidazolecarboxylic acid, its application will become more common.

Reference:
Patent; SCHERING CORPORATION; TSUI, Hon-Chung; PALIWAL, Sunil; KIM, Hyunjin, M.; KEREKES, Angela, D.; CAPLEN, Mary Ann; ESPOSITE, Sara, J.; MCKITTRICK, Brian, A.; FISCHMANN, Thierry Olivier; DOLL, Ronald, J.; RAINKA, Matthew Paul; LI, Ang; WO2011/149874; (2011); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 16042-25-4, These common heterocyclic compound, 16042-25-4, name is 2-Imidazolecarboxylic acid, 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.

The synthesis of complex 2 was similarly to 1 except that H3PW12O40¡¤13H2O (0.22g, 0.07mmol) was used instead of H3PMo12O40¡¤26H2O. The pH value was adjusted to 1.8 with molL-1 HNO3 (final pH 2.17). Yellow block crystals were filtered and washed with distilled water (35% yield based on W). Elemental Anal. Calc. for C16H15Ag2N8O49PW12 (3556.09): C 5.39, H 0.42, N 3.15. Found: C 5.43, H 0.47, N 3.11%.

Statistics shows that 2-Imidazolecarboxylic acid is playing an increasingly important role. we look forward to future research findings about 16042-25-4.

Reference:
Article; Tian, Ai-Xiang; Hou, Xue; Ying, Jun; Liu, Guo-Cheng; Ning, Ya-Li; Li, Tian-Jiao; Wang, Xiu-Li; Inorganica Chimica Acta; vol. 439; (2016); p. 43 – 48;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem