Category: 33543-78-1

Electric Literature of 33543-78-1, 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. 33543-78-1 name is Ethyl 1H-imidazole-2-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.

Ethyl 1-(5-phthalimidomethyl-1oxoindan-2yl)imidazole-2-carboxylate can be synthesised in the following way: a suspension of 28.3 g of 2-bromo-5-phthalimidomethylindan-1-one and 21.4 g of ethyl imidazole-2-carboxylate in 700 ml of toluene is heated at reflux for 24 hours. The solution is evaporated under reduced pressure and the residue is taken up in 800 ml of saturated potassium carbonate solution and 800 ml of dichloromethane. The organic phase is separated by settling and the aqueous phase is extracted twice with 500 ml of dichloromethane. The organic phases are combined, washed six times with 800 ml of distilled water, dried over magnesium sulphate and evaporated under reduced pressure. After purification of the residue by flash chromatography on a silica column (eluent: dichloromethane/methanol (99/1 by volume)), 17.5 g of ethyl 1-(5-phthalimidomethyl-1oxoindan-2yl)imidazole-2-carboxylate are obtained in the form of a beige solid (1 H NMR spectrum in d6-DMSO and a few drops of CD3 CO2 D, T=300K, delta in ppm: 1.15 (3H, t, J=7 Hz, CH3), 3.35 and 3.70 (each 1H, respectively dd, J=6 and 16 Hz, and dd, J=9 and 16 Hz, CH2), 4.10 (2H, q, J=7 Hz, OCH2), 4.93 (2H, s, NCH2), 5.79 (1H, dd, J=6 and 9 Hz, NCH), 7.20 (1H, s, CH), 7.48 (1H, d, J=7 Hz, arom. CH), 7.53 (1H, s, arom. CH), 7.56 (1H, s, arom. CH), 7.72 (1H, d, J=7 Hz, arom. CH), between 7.80 and 7.95 (4H, m, phthal. H)).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 1H-imidazole-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Rhone-Poulenc Rorer S.A.; US5902803; (1999); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 33543-78-1,Some common heterocyclic compound, 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, molecular formula is C6H8N2O2, 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 mixture of ethyl 1H-imidazole-2-carboxylate (700?mg, 5.0?mmol), potassium carbonate (1.38?g, 10.0?mmol) and 4-bromobut-1-ene (800?mg, 6.0?mmol) in 5?mL DMF was heated to 80?C for 3?h. TLC analysis indicated that the reaction had ceased. After cooling to room temperature, the solution was diluted with EtOAc (15?mL) and washed with water (25?mL?*?3), brine (25?mL?*?3). The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was then purified by SiO2 chromatography (ethyl acetate: petroleum ether?=?1:1) to give compound 9d as colorless oil (0.93?g, 96%). 1 H NMR (500?MHz, CDCl3) delta 7.14 (d, J?=?1.0?Hz, 1H), 7.05 (d, J?=?1.0?Hz, 1H), 5.80-5.70 (m, 1H), 5.08-5.01 (m, 2H), 4.47 (t, J?=?7.0?Hz, 2H), 4.41 (q, J?=?7.0?Hz, 2H), 2.59-2.50 (m, 2H), 1.43 (t, J?=?7.0?Hz, 3H); ESI-MS: m/z = 195 [M+H]+.

The synthetic route of 33543-78-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yu, Jianjun; Liu, Jieyu; Li, Daqiang; Xu, Lei; Hong, Duidui; Chang, Shan; Li, Jia; Liu, Tao; Zhou, Yubo; European Journal of Medicinal Chemistry; vol. 164; (2019); p. 423 – 439;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 33543-78-1,Some common heterocyclic compound, 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, molecular formula is C6H8N2O2, 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.

5-Phenylcarbamoyl-2-(2-ethoxycarbonylimidazolyl)-1-indanone can be prepared in the following way: the preparation is carried out as in Example 19 for 4-benzylcarbamoyl-2-(2-ethoxycarbonylimidazolyl)-1-indanone but from 3.65 g of 5-phenylcarbamoyl-2-bromo-1-indanone, 73 ml of toluene and 3.1 g of 2-ethoxycarbonylimidazole. The crude product is purified by chromatography on a silica column, elution being carried out first with a dichloromethane/methanol (99.5/0.5 by volume) mixture and then with a dichloromethane/methanol (98/2 by volume) mixture. 0.9 g of 5-phenylcarbamoyl-2-(2-ethoxycarbonylimidazolyl)-1-indanone is obtained in the form of a brown solid melting at 122¡ã C. 5-Phenylcarbamoyl-2-bromo-1-indanone can be prepared in the following way:

The synthetic route of 33543-78-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rhone-Poulenc Rorer S.A.; US5902803; (1999); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 33543-78-1,Some common heterocyclic compound, 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, molecular formula is C6H8N2O2, 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) 1-(2-Trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid ethyl ester A flask charged with 1H-imidazole-2-carboxylic acid ethyl ester (1.03 g, 7.36 mmol), K2CO3 (2.00 g, 14.5 mmol), SEM-Cl (1.56 mL, 8.89 mmol), and 20 mL of acetone was stirred for 10 h at RT. The reaction was diluted with EtOAc (100 mL), washed with NaHCO3 (2*100 mL), brine (100 mL), and the organic layer dried over Na2SO4 and concentrated. The title compound was eluted from a 20-g SPE with 50percent EtOAc/hexanes to give 1.50 g (76percent) of a colorless oil. Mass spectrum (ESI, m/z): Calcd. for C12H22N3O3Si, 271.1 (M+H), found 271.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 1H-imidazole-2-carboxylate, its application will become more common.

Reference:
Patent; Illig, Carl R.; Ballentine, Shelley K.; Chen, Jinsheng; DesJarlais, Renee Louise; Meegalla, Sanath K.; Wall, Mark; Wilson, Kenneth; US2007/249593; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 33543-78-1, These common heterocyclic compound, 33543-78-1, name is Ethyl 1H-imidazole-2-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.

Reference example 1 2-hydrazinocarbonylimidazole 2-ethoxycarbonylimidazole was prepared according to the method given in the literature, J. Org. Chem., Vol.43, No.22, 4381 Kenneth L. kirk. 80percent hydrazine hydrate (4.6g, 75mmol) was added dropwise to a solution of 2-ethoxycarbonylimidazole (2.1g, 15mmol) in ethanol (20ml) at room temperature and stirring was continued for 2 h. The precipitate was filtered, washed with water and dried to give the title compound (1.7g, 90.0percent).

Statistics shows that Ethyl 1H-imidazole-2-carboxylate is playing an increasingly important role. we look forward to future research findings about 33543-78-1.

Reference:
Patent; Wakamoto Pharmaceutical Co., Ltd.; EP713876; (1996); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 33543-78-1, The chemical industry reduces the impact on the environment during synthesis 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, I believe this compound will play a more active role in future production and life.

a solution of 3.65 g of 1,8-diazabicyclo[5.4.0]undec-7-ene in 10 ml of chloroform is added dropwise over 20 minutes at a temperature close to 20¡ã C. to a solution of 2.8 g of ethyl imidazole-2-carboxylate and 6.1 g of 2-bromo-5-chloro-1-indanone. After stirring for 2 hours and adding 100 ml of distilled water, the mixture is extracted 3 times with a total of 75 ml of chloroform and the organic extracts are pooled, dried over anhydrous magnesium sulphate and concentrated to dryness under reduced pressure (15 mmHg; 2 kPa) at 50¡ã C. After silica gel chromatography with a dichloromethane-ethyl acetate mixture (70-30 by volume), 1 g of ethyl 1-(5-chloro-1-oxo-2-indanyl)imidazole-2-carboxylate is obtained in the form of a thick yellow oil Rf=0.3, thin-layer chromatography on silica gel; solvent: dichloromethane-ethyl acetate (70-30 by[volume)]. The 2-bromo-5-chloro-1-indanone can be prepared as described in German Patent 2,640,358.

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, Ethyl 1H-imidazole-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Rhone-Poulenc Rorer S.A.; US5677306; (1997); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 33543-78-1,Some common heterocyclic compound, 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, molecular formula is C6H8N2O2, 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 mixture of ethyl lH-imidazole-2-carboxylate (1.96 g, 14.0 mmol), 3,5-dichloro-2- fluoropyridine (1.80 g, 10.8 mmol), potassium carbonate (2.24 g, 16.2 mmol), and NMP (54 mL) was heated at 115 0C for 6 h, allowed to cool to rt, and then poured into EtOAc (200 mL). The mixture was washed with water (200 mL), washed with brine (200 mL x 2), dried, filtered, concentrated, and purified by silica gel chromatography (4:1–>1 :1; hexanes: EtOAc) to give ethyl l-(3,5-dichloropyridin-2-yl)-lH-imidazole-2- carboxylate. 1H NMR (400 MHz, DMSO-d6): delta 8.68 (d, IH), 8.62 (d, IH), 7.78 (d, IH), 7.36 (d, IH), 4.15 (q, 2H), 1.13 (t, 3H); LCMS: 286.1 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 1H-imidazole-2-carboxylate, its application will become more common.

Reference:
Patent; KALYPSYS, INC.; WO2009/117421; (2009); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 33543-78-1, 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. 33543-78-1 name is Ethyl 1H-imidazole-2-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.

a mixture of 3.92 g of ethyl imidazole-2-carboxylate and 3.4 g of 2-bromo-4-cyano-1-indanone is heated at 130¡ã C. for 20 minutes, cooled to 20¡ã C. and dissolved in 20 ml of dichloromethane. The mixture is then concentrated to dryness under reduced pressure (15 mm Hg; 2 kPa) at 40¡ã C. The residue thus obtained is purified by flash chromatography on a silica column, under a nitrogen stream at medium pressure (0.5 bar), with a dichloromethane/methanol (95/5 by volume) mixture as eluent. 1.5 g of ethyl 1-[(4-cyano-1-oxoindan-2-yl)]imidazole-2-carboxylate are thus obtained, which product melts at 159¡ã C. 2-Bromo-4-cyano-1-indanone can be obtained in the following way:

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 1H-imidazole-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Rhone-Poulenc Rorer S.A.; US5902803; (1999); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 33543-78-1, name is Ethyl 1H-imidazole-2-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 33543-78-1, category: imidazoles-derivatives

SEMCI (1.519 ml_, 8.56 mmol) was added to a DMF (10 mL) suspension of K2C03 (1.972 g, 14.27 mmol) and ethyl imidazole-2-carboxylate (CAS 33543-78-1 ) (1 g, 7.14 mmol). After the mildly exothermic reaction subsided, the mixture was allowed to stir one hour at room temperature and was quenched with the addition of water and ethyl acetate. The organic phase was washed with water, brine, dried (sodium sulfate), filtered and concentrated. Purification of the residue by FCC (100percent Heptane to 50percent ethyl acetate/Heptane) afforded the title compound. MS (ESI+) m/z 271.4 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 1H-imidazole-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; BELANGER, David B.; FLOHR, Stefanie; GELIN, Christine Fang; JENDZA, Keith; JI, Nan; LIU, Donglei; LORTHIOIS, Edwige Liliane Jeanne; KARKI, Rajeshri Ganesh; MAINOLFI, Nello; POWERS, James J.; RANDL, Stefan Andreas; ROGEL, Olivier; VULPETTI, Anna; YOON, Taeyoung; WO2015/9977; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 33543-78-1, name is Ethyl 1H-imidazole-2-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 33543-78-1, SDS of cas: 33543-78-1

PREPARATION 32 1H-imidazole-2-carboxylic acid 21.75 mL (43.5 mmol) of a 2M solution of lithium hydroxide in water were added to a solution of 1.22 g (8.71 mmol) of ethyl 1H-imidazole-2-carboxylate (ref) in a mixture of tetrahydrofurane (20 mL) and water (20 mL). The reaction mixture was warmed up to reflux, and stirred for 1.5 hours. The reaction mixture was cooled to room temperature and the solvent was evaporated under vacuum. The crude residue (3.0 g) was used in next step without further purification. LRMS (m/z): 113 (M+1)+.

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; Almirall, S.A.; EP2518070; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem