Category: 33543-78-1

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.

a solution of 9.5 g of ethyl imidazole-2-carboxylate, 9.9 g of 2,5-dibromo-1-indanone and 0.1 g of sodium iodide in 280 ml of ethanol is kept boiling for 16 hours, cooled to 20¡ã C. and dried under reduced pressure (20 mmHg; 2.6 kPa) at 50¡ã C. The product obtained (21 g) is dissolved in 50 ml of dichloromethane and the solution is washed 3 times with a total of 600 ml of distilled water, dried over anhydrous magnesium sulphate and dried under reduced pressure (20 mmHg; 2.6 kPa) at 50¡ã C. The product obtained (12.7 g) is chromatographed on 790 g of neutral silica gel (0.020-0.045 mm) contained in a column 7 cm in diameter, eluding under pressure with a dichloromethane-ethyl acetate mixture (70-30 by volume) and collecting 75-ml fractions. Fractions 70 to 140 are pooled and concentrated to dryness under reduced pressure (15 mmHg; 2 kPa) at 40¡ã C. 3.7 g of ethyl 1-(5-bromo-1-oxo-2-indanyl)imidazole-2-carboxylate are thus obtained which melt at 140¡ã C. The 2,5-dibromo-1-indanone can be prepared as described in European Patent 346107.

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; Rhone-Poulenc Rorer S.A.; US5677306; (1997); 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, Recommanded Product: Ethyl 1H-imidazole-2-carboxylate

To a solution of ethyl 1H-imidazole-2-carboxylate (500 mg, 3.57 mmol) in DMF (10 mL) were added tert-butyl (2-bromoethyl)carbamate (800 mg, 3.57 mmol) and K2CO3 (986 mg, 7.14 mmol), and the resulting white suspension was stirred at 60 C. for 16 h, allowed to cool to RT, then concentrated under reduced pressure. The residue was purified by SiO2 gel chromatography (20% to 100% EtOAc in hexanes) to give the title compound as a white solid (751 mg, 74%). MS (ES+) C13H21N3O4 requires: 283, found: 284 [M+H]+.

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; Board of Regents, The University of Texas System; LE, Kang; SOTH, Michael J.; JONES, Philip; CROSS, Jason Bryant; CARROLL, Christopher L.; MCAFOOS, Timothy Joseph; MANDAL, Pijus Kumar; US2019/298729; (2019); 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, HPLC of Formula: C6H8N2O2

To a suspension of ethyl lH-imidazole-2-carboxylate (40.01 g, 285.5 mmol) in dried THF (600 mL) was added sodium hydride (13.82 g, 345.5 mmol, 60 mass%) at 0 C. The mixture was stirred at room temperature for 1 h, and then cooled down to 0 C. To the mixture was added ( -(2,4-dinitrophenyl)hydroxylamine (80.00 g, 401.8 mmol) in portions, and then the resulted mixture was stirred at room temperature overnight. The mixture was diluted with water (600 mL), and the resulted mixture was extracted with EA (600 mLchi10). The combined organic layers were dried over anhydrous Na2SC>4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (EA/PE (v/v) = 1/2 to 1/1 to 2/1) to afford the title compound as a brown solid (37.6 g, yield 85%).MS (ESI, pos. ion) m/z: 156.1 [M + H]+;NMR (400 MHz, CDCb) delta (ppm): 7.19 (s, IH), 7.07 (s, IH), 5.82 (s, 2H), 4.43 (q, J = 7.1 Hz, 2H), 1.44 (t, J = 7.1 Hz, 3H).

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; SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES, LLC; XI, Ning; LI, Xiaobo; LI, Mingxiong; ZHANG, Tao; HU, Haiyang; WU, Yanjun; (139 pag.)WO2018/169700; (2018); A1;,
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. 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, A new synthetic method of this compound is introduced below., COA of Formula: C6H8N2O2

The ethyl 1-(4-chloro-1-oxo-2-indanyl)-imidazole-2-carboxylate can be prepared as in Example 1 for the preparation of ethyl 1-(5-fluoro-1-oxo-2-indanyl)imidazole-2-carboxylate but starting with 2.8 g of ethyl imidazole-2-carboxylate, 0.6 g of 80percent sodium hydride, 6.4 g of 2-bromo-4-chloro-1-indanone and a total of 80 ml of anhydrous dimethylformamide. After silica gel chromatography with a dichloromethane-ethyl acetate mixture (80-20 by volume), 1.85 g of ethyl 1-(4-chloro-1-oxo-2-indanyl)imidazole-2-carboxylate are obtained Rf=0.3, thin-layer chromatography on silica gel; solvent: dichloromethane-ethyl acetate (80-20 by[volume)]. The 2-bromo-4-chloro-1-indanone can be prepared in the following manner:

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.; US5677306; (1997); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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.

A solution of the required amine (0.20 mmol; 2 eq.) in DMF (0.2 mL), in a glass vial under inert atmosphere (N2), is treated with NaH (3.3 eq.) at rt. After 10 min, it is treated with a solution of the chloride (0.10 mmol; 1 eq.) in DMF (0.8 mL) and the reaction mixture is stirred at rt and monitored by LC-MS. Upon reaction completion, the reaction mixture is quenched by the addition of a sat. aq. KH2P04 solution and the reaction mixture is stirred at rt for 20 h. The reaction mixture is concentrated under reduced pressure and purification of the residue gives the desired product. Starting from the compound of Preparation R and ethyl imidazole-2-carboxylate and proceeding in analogy to Procedure AQ, the title compound was obtained, after purification by prep-HPLC (basic conditions), as an amorphous solid (22percent yield).MS (ESI, m/z): 340.10 [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; ACTELION PHARMACEUTICALS LTD; BUR, Daniel; GUDE, Markus; HUBSCHWERLEN, Christian; PANCHAUD, Philippe; WO2011/121555; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 33543-78-1, 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 33543-78-1 as follows.

Compound 52 was alkylated in sequence with ethyl bromoacetate, isopentyl iodide, and iodomethane to give compound 55. Hydrolysis of compound 55, followed by a treatment with TMS-Eto-acetylene, gave the cyclic anhydride 57. Reaction of compound 57 with diethyl malonate gave compound 58, which coupled with compound 11 to yield the compound 215.

According to the analysis of related databases, 33543-78-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INTERMUNE, INC.; US2009/257979; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., 33543-78-1

To a stirred solution of hydroxylamine-o-sulfonic acid (26.64 g, 235.8 mmol, 3.0 eq) in H20 (17 mL) at 0 C, ethyl lH-imidazole-2-carboxylate (11.0 g, 78.6 mmol, 1.0 eq) was added and the resulting mixture was stirred at 90 C for 30 min. The mixture was cooled to RT and K2CO3 (3.6 g, 26.2 mmol, 1.0 eq) was added in portions. The resulting mixture was stirred at RT overnight, filtered and rinsed with H20 (10 mL x 3). The filtrate was extracted with ethyl acetate (50 mL x 5). The combined organic layer was washed with brine, dried over Na2S04 and filtered. The filtrate was evaporated in vacuo and the residue was purified by flash column chromatography on silica gel (1% MeOH in DCM) to afford ethyl 1 -amino- lH-imidazole-2-carboxylate (800 mg, 6.5 % yield). ESI-MS m/z: 156.1 [M+H]+.

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; INFINITY PHARMACEUTICALS INC.; INTELLIKINE, LLC; CASTRO, Alfredo, C.; EVANS, Catherine, A.; JANARDANANNAIR, Somarajannair; LESCARBEAU, Andre; LIU, Tao; SNYDER, Daniel, A.; TREMBLAY, Martin, R.; REN, Pingda; LIU, Yi; LI, Liansheng; CHAN, Katrina; WO2013/12915; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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.

Description 45; Ethyl 1-(4-formylphenyl)-1H-imidazole-2-carboxylate (D45); Ethyl imidazole-2-carboxylate (140mg, 1. Ommol), 4-formylbenzeneboronic acid (300mg, 2.0mmo.) and catalyst [Copper(OH).TMEDA] 2CI2 (46mg, 0.1 Ommol) were dissolved in 1 ,2-dichloroethane (5ml) and heated to 60¡ãC under an O2 atmosphere for 2Oh. The mixture was diluted with DCM, filtered through Celite and evaporated to dryness. The crude residue was purified by column chromatography on silica, eluting with a 0-5percent [2M NH3 in MeOH]/DCM gradient to give the title compound (152mg). deltaH (CDCI3, 250MHz) 1.32 (3H, t), 4.32 (2H, q), 7.22 (1 H, s), 7.34 (1H, s), 7.52 (2H, d), 8.01 (2H, d), 10.11 (1H, s). MS (ES): MH+ 245.

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; GLAXO GROUP LIMITED; WO2007/7018; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

33543-78-1, 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. 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

Example 92 A mixture of 4-[4-(4-chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolyl]butyl methanesulfonate(600 mg), ethyl 2-imidazolecarboxylate(410 mg), potassium carbonate(405 mg) and N,N-dimethylformamide (30 ml) was stirred for 2 hours at 80-90¡ã C. Water was added to the reaction mixture. This was extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried (Mg SO4). The residue obtained by evaporating the solvent was subjected to silica gel column chromatography. From the fraction eluted with acetone-hexane (1:1, v/v), obtained was ethyl 1-[4-[4-(4-chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolyl]butyl)-2-imidazolecarboxylate as crystals (460 mg, 69percent). This was recrystallized from acetone-isopropyl ether to give colorless prisms. mp 134-135¡ã C.

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; Takeda Chemical Industries, Ltd.; US6177452; (2001); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

33543-78-1, 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. 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, A new synthetic method of this compound is introduced below.

Synthesis of Ethyl 1~((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2- carboxylate (lnt~1a) ciInMa2-(Trimethylsilyl)ethoxymethyi chloride (12.8 g, 0.077 mol) was added to a stirred solution of ethyl imidazole-2-carboxylate (9.0 g, 0.064 mol) and potassium carbonate (17.7 g, 0.128 mol) in NtN-dimethylformamide (50 mL) at 0 ¡ãC. The mixture was allowed to stir from 0 ¡ãC to r.t. overnight. Water and ethyl acetate were added and the layers were separated. The separated aqueous layer was extracted with ethyl acetate (X2). The combined organic layers were washed with water (X2). The separated organic layer was dried (MgS04) and filtered. The solvents were removed in vacuo andchromatographic purification (ethyl acetate – hexane) of the residue gave imidazole InMa (12 g, 70percent) as a colorless oil. LCMS m/e (M + H+) – 271.1.

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; 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