Category: 51605-32-4

51605-32-4, name is Ethyl 5-methyl-1H-imidazole-4-carboxylate, 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. Computed Properties of C7H10N2O2

Methyl 2-fluoro-5-nitrobenzoate (21.9 g, 0.11 mol) and ethyl 4-methyl-5-imidazole-carboxylate (15.4 g, 0.1 mol) were dissolved in DMSO (150 mL). Cesium carbonate (32.6 g, 0.1 mol) was added and the mixture was stirred at RT for 24 h. TLC analysis (ethyl acetate) showed a new spot with Rf 0.4. The reaction mixture was poured into ice water and left to stand for 3 hours. A precipitate could be seen at the bottom of the flask. The solid was isolated by filtration, after washing with water several times. The product (31.3 g) was obtained in yield 94percent. 1H NMR (300 MHz, CDCl3): dH 1.45 (3H, t, J = 7.1 Hz, COOCH2CH3), 2.33 (3H, s, NCCH3), 3.72 (3H, s, COOCH3), 4.39 (2H, q, J = 7.1 Hz, COOCH2CH3), 7.47 (1H, s, NCHN), 7.52 (1H, d, J = 8.6 Hz, CCHCHCNO2CH), 8.53 (1H, dd, J = 8.6 and 2.8 Hz, CCHCHCNO2CH), 8.94 (1H, d J = 2.8 Hz, CCHCHCNO2CH).

The synthetic route of 51605-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jackson, Alexander; Guilbert, Benedicte B.; Plant, Stuart D.; Goggi, Julian; Battle, Mark R.; Woodcraft, John L.; Gaeta, Alessandra; Jones, Clare L.; Bouvet, Denis R.; Jones, Paul A.; O’Shea, Dennis M.; Zheng, Penny Hao; Brown, Samantha L.; Ewan, Amanda L.; Trigg, William; Bioorganic and Medicinal Chemistry Letters; vol. 23; 3; (2013); p. 821 – 826;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 51605-32-4, These common heterocyclic compound, 51605-32-4, name is Ethyl 5-methyl-1H-imidazole-4-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.

Lithium hexamethyldisilazide (iM in tetrahydrofuran, 2i.4 ml, 2i.4 mmol) was added dropwise over iS mm to a stirred, cooled (-iO C) suspension of ethyl 4-methyl-i H25 imidazole-S-carboxylate (3.00 g, i9.S mmol) in dry dimethylformamide (200 ml) underan atmosphere of argon. After stirring for a further iO mi 0- (diphenylphosphoryl)hydroxylamine (5.45 g, 23.4 mmol) was added and the mixture was warmed to room temperature. After 6 h, water was added until a clearhomogeneous solution formed and subsequently the mixture was evaporated todryness. The resultant solid was treated with dichloromethane and the mixture wasfiltered and the filter cake was washed with further portions of dichloromethane. Thecombined filtrate and washings were evaporated to give a solid which was purified byflash chromatography (methanol-dichloromethane gradient, 0:100 rising to 5:95) togive 1.75 g (10.3 mmol, 53% yield) of the title compound as a white solid. Purity 100%.1H NMR (300 MHz, Chloroform-d) ppm 7.59 (s, 1H), 5.33 (br s, 2H), 4.37 (q, 2H, J =7.4 Hz), 2.46 (s, 3H), 1.40 (t, 3H, J = 7.4 Hz).UPLC/MS (3 mm) retention time 0.56 mm.LRMS: m/z 170 (M+1).

The synthetic route of 51605-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMIRALL, S.A.; AIGUADE BOSCH, Jose; CONNOLLY, Stephen; EASTWOOD, Paul Robert; GOMEZ CASTILLO, Elena; MORENO MOLLO, Immaculada Montserrat; ROBERTS, Richard Spurring; SEVILLA GOMEZ, Sara; (216 pag.)WO2017/60488; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 51605-32-4, name is Ethyl 5-methyl-1H-imidazole-4-carboxylate, 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 51605-32-4, Application In Synthesis of Ethyl 5-methyl-1H-imidazole-4-carboxylate

ETHEI 1 4-DIMETHVL-1H-IMIDAZOLE-5-CARBOXYLATE] To a solution of the [AVAILABLE ETHYL 4-METHYL-1 H-IMIDAZOLE-5-CARBOXYLATE] (5.0 [G,] 32.5 [MMOL)] in DMF (50 mL) was added [NAHC03] (5.72 g, 2. [1EQ.)] and methyl iodide (2.43 [ML, 1.2 EQ. ). THE REACTION WAS STIRRED AT 90XB0;C DURING 5 DAYS. AFTER EVAPORATION OF THE] solvant, the residue was diluted in DCM and washed with water. The organic layer was dried over [NA2SO4] and evaporated off. After purification by flash chromatography using DCM as eluent, the title compound was obtained as a yellow oil (1.69 g, 0.01 mol) in [31percent] yield;’H NMR (CDCI3, 300 MHz) [6] 7.86 (s, 1H), 4.36 (q, 2H), 3.89 (s, 3H), 2.47 (s, 3H), 1.4 (t, 3H)

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; GLAXO GROUP LIMITED; WO2004/6922; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 51605-32-4, name is Ethyl 5-methyl-1H-imidazole-4-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. COA of Formula: C7H10N2O2

A. N-(2-Fluorophenyl)-5-methyl-1H-imidazole-4-carboxamide To ethyl-4-methyl-5-imidazolecarboxylate (5 g, 32.4 mmol) was added 20 mL of 2-fluoroaniline and potassium carbonate (8.9 g, 64.8 mmol). The reaction mixture was heated to reflux for 18 h then cooled to room temperature and concentrated in vacuo. Water and hexane were added and the precipitate filtered to give the crude product.

The synthetic route of Ethyl 5-methyl-1H-imidazole-4-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Co.; US6235740; (2001); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 51605-32-4, 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 51605-32-4 as follows.

Hydrolysis of ethyl-4-methyl-1H-imidazole carboxylate(7, 3.0 g, 19.5 mmol) was carried out in a basic medium offreshly prepared 2 M NaOH solution for 3 h. Neutralizationwith glacial acetic acid was performed after the completionof the reaction. The aqueous solvent was evaporated underreduced pressure and 10 mL of absolute ethanol was used tore-dissolve the white solid product. The reaction mixture wasfiltered off and the precipitate was dissolved several timeswith absolute ethanol and co-evaporation was performed toremove water traces. 4-Methyl-1H-imidazole-5-carboxylic acid(8) was obtained as a white solid with a yield of 87.8%.

According to the analysis of related databases, 51605-32-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Jasim, Suhair H.; Sheikha, Ghassan M. Abu; Abuzaid, Haneen M.; Al-Qirim, Tariq M.; Shattat, Ghassan F.; Sabbah, Dima A.; Ala, Samah A.; Aboumair, Mustafa S.; Sweidan, Kamal A.; Bkhaitan, Majdi M.; Chemical and Pharmaceutical Bulletin; vol. 66; 10; (2018); p. 953 – 958;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 51605-32-4, name is Ethyl 5-methyl-1H-imidazole-4-carboxylate, molecular formula is C7H10N2O2, 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. HPLC of Formula: C7H10N2O2

To an oven- dried three-neck reaction flask charged with a magnetic stir bar, an internal thermometer at rt under argon was added ethyl 4-methyl-lH-imidazole-5- carboxylate (2.20 g, 14.3 mmol) and anhydrous DMF (71 mL). The yellow solution was cooled to -20C using a dry ice and EtOAc bath. Lithium hexamethyldisilane (1.0M in TetaF, 15.7 mL, 15.7 mmol) was then added dropwise via an addition funnel while maintaining the internal temperature below -12C. To the solution was then added o-(diphenylphosphinyl)- hydroxylamine (4.00 g, 17.1 mmol) in two portions while maintaining the internal temperature at O0C. The resulting white suspension was diluted by the addition of DMF (15 mL) and stirred at rt overnight. The white suspension was quenched with water (5 mL) and the solvent was removed under vacuum. The resulting yellow solid was extracted with CH2Cl2 (50 mL), EtOAc (100 mL) and then the organic extracts were combined and concentrated by rotary evaporation to a brown solid. It was purified by flash column chromatography (80 g pre-packed silica gel column, gradient elution with CH2Cl2, to CH2Cl2:Me0H, 4:96) to give 1.00 g (41%) of the title compound as a white solid. 1H NMR (CDCl3) 7.59 (s, I H), 5.32 (br s, 2H), 4.36 (q, J= 7.1 Hz, 2H), 2.45 (s, 3H), 1.40 (t, J= 7.0 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 51605-32-4, its application will become more common.

Reference:
Patent; CYTOVIA, INC.; WO2008/57402; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 51605-32-4, 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 51605-32-4 as follows.

(1) Ethyl 5-methyl-1H-imidazole-4-carboxylate (Sigma-Aldrich Co., Ltd.) (7.5g, 48.7mmol) in acetonitrile (120mLWas dissolved in), there N-bromosuccinimide (10.4g, 58.4mmol) added The mixture was stirred at room temperature for 3 hours on. After the reaction, a saturated sodium hydrogen carbonate aqueous solution was added, with ethyl acetateIt was extracted twice. The organic layer was washed with saturated brine, and dried with anhydrous sodium sulfate. concentratedAfter it was purified by column chromatography, ethyl 2-bromo-4-methyl-1H-imidazole-5-carboxylate

According to the analysis of related databases, 51605-32-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TEIJIN PHARMA LIMITED; MARUYAMA, AKINOBU; KAMADA, HIROFUMI; FUJINUMA, MIKA; TAKEUCHI, SUSUMU; SAITO, HIROSHI; TAKAHASHI, YOSHIMASA; (95 pag.)JP2015/214527; (2015); A;,
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. 51605-32-4, name is Ethyl 5-methyl-1H-imidazole-4-carboxylate, A new synthetic method of this compound is introduced below., Product Details of 51605-32-4

To a mixture of ethyl 4-methyl-1H-imidazole-5-carboxylate (7.30 g, 45.9 mmol) in THF (60 mL) is added MeOH (2.23 mL, 55.1 mmol) and triphenylphosphine (14.8 g, 55.1 mmol). The reaction is cooled to 0° C. under N2 and diethyl azodicarboxylate (9.0 mL, 17.6 mmol) is added dropwise. The mixture is warmed to room temperature and stirred overnight. The volatiles are evaporated in vacuo. Ether (50 mL) is added. The mixture is stirred at room temperature for 30 minutes, filtered, the filter cake is washed with ether (50 mL). The filtrate and ether washings are combined and are sequentially washed with water (30 mL) and brine (30 mL). The organic phase is dried over Na2SO4, evaporated in vacuo to provide the crude product. The crude product is subjected to silica gel flash column eluting with 30percent EtOAc in hexanes to EtOAc to give the title compound (5.13 g, 59.8percent) as a yellow oil. LC/MS (m/z): 169 (M+H).

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; Eli Lilly and Company; Hu, Zhi Long; Liu, Lian Zhu; Ma, Tianwei; Zhang, Haizhen; Zhou, Jingye; (25 pag.)US2018/194755; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 51605-32-4, name is Ethyl 5-methyl-1H-imidazole-4-carboxylate, 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 51605-32-4, Quality Control of Ethyl 5-methyl-1H-imidazole-4-carboxylate

[2757] To a stirred solution of 964 (Ethyl 4-methyl-5-imidazole carboxylate, 7.7 g, 50 mmol) in 100 ml of acetone at room temperature, was added K2CO3 (6.9 g, 50 mmol) portionwise. Stirred at room temperature for 25 minutes, added in MeI (5 ml, 80 mmol) stirred for 21/2 h, (monitored reaction by TLC). Additional K2CO3 (3.09 g, 22 mmol) and MeI (3 ml) were added. Stirred reaction for 16 h, then filtered reaction mixture and rinsed with acetone (80 ml). A clear filtrate obtained. Filtrate was evaporated and the residue was chromatographed (eluent methylene chloride/methanol (60:1) to afford 1.8 g of solid. This solid was purified by Prep Plate chromatography ((20:1) CH2Cl2:MeOH NH3), compound still impure. Another column chromatography ((50:1) CH2Cl2:MeOH.NH3) was done to afford 383 mg of the desired product, compound 965.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 5-methyl-1H-imidazole-4-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Schering Corporation; US2004/122018; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 51605-32-4, A common heterocyclic compound, 51605-32-4, name is Ethyl 5-methyl-1H-imidazole-4-carboxylate, molecular formula is C7H10N2O2, 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.

Ethyl 4-methyl-1 H-imidazole-5-carboxylate (463 mg, 3.00 mmol, 1 eq) was combined with iodomethane (0.19 mL, 3.00 mmol, 1 eq) and potassium carbonate (828 mg, 6.00 mmol, 2 eq) in acetonitrile and stirred overnight at reflux. The reaction mixture was cooled to ambient temperature, inorganics filtered off, and the filtrate concentrated to dryness. The residue was purified on an 80 g silica gel cartridge eluted with 100percent EtOAc to 10percent CH3OH/DCM to give the two regioisomeric products. The first eluting isomer was identified as the title compound (185 mg, 1.95 mmol, 35percent) by comparative NOESY and HMBC NMR. 1 H NMR (400 MHz, DMSO- d6) delta ppm 7.74 (s, 1 H), 4.25 (q, J=7.14 Hz, 2 H), 3.76 (s, 3 H), 2.34 (s, 3 H), 1.30 (t, J=7.10 Hz, 3 H). LC-MS (ES+) m/z 169.08 [M+H]

The synthetic route of 51605-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/157273; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem