Category: 51605-32-4

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, HPLC of Formula: C7H10N2O2

[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

Related Products 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

Application of 51605-32-4, 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. 51605-32-4, name is Ethyl 5-methyl-1H-imidazole-4-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 24-1 (0.5g, 2.4mmol) in EtOH (2ml) was added 3N LiOH (2.2ml, 6.5mmol). The reaction mixture was heated at 800C for Ih. The heat was reduced to 400C and the mixture was stirred overnight. The mixture was then heated at 800C for an additional 5.5h. The reaction was neutralized with 12N HCl and was concentrated in vacuo. The residue was dried azeotropically with toluene to afford the desired product 24-2 as a solid. MS calculated M+H: 127.1, found 127.1

The chemical industry reduces the impact on the environment during synthesis Ethyl 5-methyl-1H-imidazole-4-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK & CO., INC.; WO2006/135627; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

51605-32-4, 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. 51605-32-4 name is Ethyl 5-methyl-1H-imidazole-4-carboxylate, 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.

Using a modified procedure of Sreedhar. (Reference: Sreedhar, B., Synthesis, 795 (2008)). To a suspension of ethyl 4-methyl-1H-imidazole-5-carboxylate (0.530 g, 3.44 mmol) and (3-chloro-2-fluorophenyl)boronic acid (0.500 g, 2.87 mmol) in MeOH (5.74 mL) was added cuprous oxide (0.041 g, 0.287 mmol). The resulting purple suspension was stirred vigorously under an atmosphere of air (drying tube used). After 20 h, thereaction mixture was filtered to remove the solids and the clear blue filtrate was concentrated to give a blue solid. The blue solid was suspended in DCM and filtered to remove the solids and the blue filtrate was concentrated to give a pale blue solid weighing 0.187 g. Purification by normal phase chromatography gave ethyl 1-(3-chloro-2- fluorophenyl)-4-methyl- 1H-imidazole-5-carboxylate (0.0187 g, 2percent) as a clear, colorlessresidue and ethyl 1 -(3 -chloro-2-fluorophenyl)-5 -methyl- 1H-imidazole-4-carboxylate (Intermediate 24A) (0.0079 g, 1percent) as a clear, colorless residue. MS(ESI) m/z: 283.1 (M+H)

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; BRISTOL-MYERS SQUIBB COMPANY; PABBISETTY, Kumar Balashanmuga; CORTE, James R.; DILGER, Andrew K.; EWING, William R.; ZHU, Yeheng; (178 pag.)WO2017/19819; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products 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.

A. To a stirred suspension of ethyl 4-methyl-1H-imidazole-5-carboxylate (2.00 g, 13.0 mmol) in acetonitrile (25 mL) and chloroform (25 mL) was added N-bromosuccinimide (2.31 g, 13.0 mmol). The reaction mixture was stirred under nitrogen atmosphere for 20 h, then concentrated in vacuo. The residue was dissolved in ethyl acetate (100 mL) and washed with saturated aqueous sodium bicarbonate (50 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluding with 50percent ethyl acetate in hexanes to afford ethyl 2-bromo-4-methyl-1H-imidazole-5-carboxylate as a light yellow solid (1.88 g, 62percent): 1H NMR (300 MHz, CDCl3) delta 4.35 (q, J=7.1 Hz, 2H), 2.51 (s, 3H), 1.37 (t, J=7.1 Hz, 3H); MS (ES+) m/z 233.1 (M+1), 235.1 (M+1).

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

Reference:
Patent; Dales, Natalie; Fonarev, Julia; Fu, Jianmin; Hou, Duanjie; Kamboj, Rajender; Kodumuru, Vishnumurthy; Pokrovskaia, Natalia; Raina, Vandna; Sun, Shaoyi; Zhang, Zaihui; US2009/156615; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 51605-32-4,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.

and also, starting from 4-methylimidazole-5-carboxylic acid ethyl ester, 1-(2,6-difluorobenzyl)-4-methylimidazole-5-carboxylic acid ethyl ester, m.p. 59°-61° (from hexane) and 1-(2,6-difluorobenzyl)-5-methylimidazole-4-carboxylic acid ethyl ester, m.p. 107°-108° (from toluene/ether), 1-(o-chlorobenzyl)-4-methylimidazole-5-carboxylic acid ethyl ester, m.p. 74°-76°, and 1-(o-chlorobenzyl)-5-methylimidazole-4-carboxylic acid ethyl ester, m.p. 100°-104°; and also, starting from imidazole-4,5-dicarboxylic acid diethyl ester, 1-(2,6-difluorobenzyl)-imidazole-4,5-dicarboxylic acid diethyl ester, m.p. 71°-73° (from petroleum ether), 1-(o-chlorobenzyl)-imidazole-4,5-dicarboxylic acid diethyl ester, m.p. 69°-70° (from ether/hexane) and 1-(o-methylbenzyl)-imidazole-4,5-dicarboxylic acid diethyl ester (oil); and also, starting from 2-methylimidazole-4,5-dicarboxylic acid diethyl ester, 1-(2,6-difluorobenzyl)-2-methylimidazole-4,5-dicarboxylic acid diethyl ester, m.p. 63°-64° (from ether/hexane).

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

Reference:
Patent; Ciba-Geigy Corporation; US4851424; (1989); A;,
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 51605-32-4 as follows. COA of Formula: C7H10N2O2

(5-Methylimidazol-4-yl)methylchloride hydrochloride (14) A paste of ethyl 4-methyl-5-imidazolecarboxylate (37.5 g, 0.243 mol) and a little dry THF was added in portions to a stirred suspension of LiAlH4 (12.0 g, 0.316 mol) in 1.0 L of dry THF under a flow of nitrogen. After refluxing for 4 h, the suspension was cooled in an ice-water bath and the excess LiAlH4 destroyed with successive additions of 12 mL of H2 O, 12 mL of 15percent NaOH, and 45 mL of H2 O. The white suspension was brought to room temperature (2 h) and filtered. After collecting the precipitate, it was digested in hot THF (500 mL), cooled, and filtered again. The total THF filtrate was concentrated in vacuo, the residual orange oil was dissolved in a minimum amount of EtOH, and 500 mL of hot EtOAc:Et2 O (3:2) was added. The solution was chilled yielding 15.0 g (55percent) of (5-methylimidazol-4-yl)methanol as white prisms: mp 138° (lit. 138°). This material (9.6 g, 0.086 mol) was dissolved in 50 mL of conc HCl and heated on a steam bath for 30 min. The acidic mixture was concentrated in vacuo to dryness and the solid dissolved in a minimum amount of EtOH. With the addition of a little dry Et2 O, 14 (8.5 g, 67percent) precipitated as a white powder: mp 236°-237° (lit. 222°).

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; Research Corporation; US4432983; (1984); A;,
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. 51605-32-4, name is Ethyl 5-methyl-1H-imidazole-4-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 51605-32-4

N-Amination of ethyl 5-methyl-3H-imidazole-4-carboxylic acid (5.39 g, 34.96 mmol) following the general procedure. Purification by flash chromatography on silica gel eluting with 0% increasing to 4% methanol in dichloromethane gave a yellow-white solid (4.23 g, 71%). Rf 0.53 (7% MeOH in DCM), 1H NMR (300 MHz, CDCl3): delta 7.48 (s, 1H), 5.33 (s, 2H), 4.27 (q, J=6.9 Hz, 2H), 2.35 (s, 3H), 1.31 (t, J=6.9 Hz, 3H). 13C NMR (75 MHz, CDCl3): delta 61.9 (CO2Et), 146.6, 140.4 (CH), 118.4, 60.8, 16.4, 14.7. MS, m/z (%) 170 (100) [M++1] Anal. Calcd for C7H11N3O2 (169.18): C, 49.70; H, 6.55; N, 24.84. Found: C 49.85, H 6.45, N 24.74.

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

Reference:
Patent; Heim-Riether, Alexander; Rotella, David Paul; US2006/264624; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 51605-32-4,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.

Step 1 To a stirred suspension of 5.4 g ethyl 4-methyl-5-imidazolecarboxylate in 30 ml tetrahydrofuran were added 1.4 g sodium hydride in mineral oil (60percent) in portions at ambient temperature under argon atmosphere. After gas formation ceased, 2.24 ml methyl iodide were added dropwise at 0° C., then the mixture was stirred at ambient temperature overnight. The precipitate was filtered off and the filtrate was concentrated. The resulting residue was purified by column chromatography eluted with dichloromethane:methanol (100:0->87:13) to give pure intermediate I.4. Yield: 1.0 g of 1.4 (17percent of theory) Analysis: [M+H]+=169; HPLC-MS (method G): Rt=0.76 min

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 5-methyl-1H-imidazole-4-carboxylate, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; DAHMANN, Georg; DOLLINGER, Horst; GNAMM, Christian; FIEGEN, Dennis; HOFFMANN, Matthias; KLICIC, Jasna; LAMB, David James; SCHNAPP, Andreas; US2013/281430; (2013); A1;,
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. category: imidazoles-derivatives

(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

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; 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