Category: 33543-78-1

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. 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of Ethyl 1H-imidazole-2-carboxylate

Ethyl 1-amino-1H-imidazole-2-carboxylate To a stirred suspension of ammonium chloride (228 g, 4.28 mol) in MTBE (2.4 L), aq. NH3 (1.2 L) was added at -20 C., prior to the addition of 11-14% sodium hypochlorite (3.5 L, 4.79 mol) at the same temperature over a period of 30 min. The reaction mixture was stirred at the same temperature for 1 h, after which the MTBE layer was separated and washed with brine solution. MTBE layer was dried over Na2SO4 and kept in the refrigerator and used immediately. In an another flask NaH (20 g, 513.9 mmol) was suspended in DMF (600 mL) at -10 C., to which a solution of ethyl 1H-imidazole-2-carboxylate (60 g, 428.2 mmol) in DMF (150 mL) was added slowly. The reaction mixture was stirred at room temperature for 1.5 h and cooled to -20 C., prior to the drop-wise addition of the chloramine solution in MTBE. The reaction was stirred at -10 C. for 1 h and at room temperature for 2 h. The reaction was monitored by TLC. After completion of the reaction, the reaction mixture was cooled to 0 C. and quenched with 1 L of 10% Na2S2O3 solution. Organic layer was separated; and the aqueous layer was extracted with EtOAc. The combined organic layer was washed with brine (500 mL), dried over Na2SO4, filtered and evaporated to get crude ethyl 1-amino-1H-imidazole-2-carboxylate as a solution in DMF, which was used in the next step as such. A small portion of the solution was dried in vacuo to remove DMF and the product was characterized by 1H-NMR and LC-MS. ES+, m/z 156.3 [M+1].

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

Reference:
Patent; Polaris Pharmaceuticals; WEBBER, Stephen E.; TAO, Xueliang; BRIN, Elena; (85 pag.)US2017/369489; (2017); 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, Safety of Ethyl 1H-imidazole-2-carboxylate

Ethyl 1H-imidazole-2-carboxylate at 0 C(40.01 g, 285.5 mmol) in a dry THF (600 mL) suspension Sodium hydride (13.82 g, 345.5 mmol, mass fraction 60%) was added.The reaction mixture was stirred at room temperature for 1 hour and then cooled to 0 C.O-(2,4-dinitrophenyl)hydroxylamine (80.00 g, 401.8 mmol) was added portionwise.The reaction system was stirred at room temperature overnight and then diluted in water (600 mL).The resulting mixture was extracted with EA (600 mL×10).The separated organic phase was dried over anhydrous sodium sulfate, filtered and evaporated.The residue obtained is purified by silica gel column chromatography (EA/PE (v/v) = 1/2 to 1/1 to 2/1).The title compound is a brown solid(37.6 g, yield 85%).

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Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Li Xiaobo; Li Minxiong; Zhang Tao; Hu Haiyang; Wu Yanjun; (102 pag.)CN108570048; (2018); 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. 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, A new synthetic method of this compound is introduced below., SDS of cas: 33543-78-1

General procedure: A mixture of 0.68 g of imidazole, 2.13 g of oxidant(chloramine-B) in presence of 2.5 cm3 (0.01 mol dm-3) of aqueous perchloric acid was stirred at 303 K for 8?10 h. After completion of the reaction (monitored by TLC), the reaction products were neutralized with alkali and extracted with ether. The organic products were subjected to spottests and chromatographic analysis (TLC technique). Further, the reaction mixture was extracted with ethyl acetate and dried over sodium sulfate. The solvent was evaporated under reduced pressure to obtain crude products. The crude products were purified on silica gel column by using petroleum ether and ethyl acetate as solvents to get the pure products. Above analyses revealed the formation of corresponding imidazolones as the oxidation products of imidazoles. 3,5-Dihydroimidazol-4-one, 2-methyl-3,5-dihydroimidazol-4-one, 2-ethyl-3,5-dihydroimidazol-4-one,3,5-dihydro-4-oxoimidazol-2-carbaldehyde, and 3,5-dihydro-4-oxoimidazol-2-ester are the oxidation products of1H-imidazole, 2-methyl-1H-imidazole, 2-ethyl-1H-imidazole,1H-imidazole-2-carbaldehyde, and 1H-imidazole-2-ester, respectively. The mass spectra showed a molecularion peak at m/z = 84 amu (Fig. 1), 99 amu (M 1,Fig. 2), and 112 amu (Fig. 3), clearly confirming 3,5-dihydroimidazol-4-one, 2-methyl-3,5-dihydroimidazol-4-one, and 2-ethyl-3,5-dihydroimidazol-4-one as oxidation products of 1H-imidazole, 2-methyl-1H-imidazole, and2-ethyl-1H-imidazole, respectively. Further these productswere confirmed by NMR data (supplementary material,Figs. 1s?3s). Furthermore, we have succeeded in estimating the products, imidazolones, in case of all the five imidazoles. In some typical experiments, the weight of imidazolones and their percentage yield obtained are recorded in Table 1. The recovery of imidazolones was 87?93 percent yields. Further no reaction was noticed between oxidation products and CAB under prevailing experimental conditions.

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

Reference:
Article; Manjunatha; Puttaswamy; Monatshefte fur Chemie; vol. 147; 9; (2016); p. 1517 – 1529;,
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.

[1122] to a mixture of ethyl 1H-imidazole-2-carboxylate (5 g, 35.7 mmol) and phenylboronic acid (8.7 g, 71.4 mmol) in dce (150 ml) was added Cu(OAc)2 (7.13 g, 39.25 mmol), pyridine (5.64 g, 71.36 mmol, 5.76 ml), 4a° ms (3 g). The mixture was stirred at 60 °C for 16 hours under 02. The reaction mixture was filtered and the filtrate was concentrated. The crude product was purified by silica gel chromatography eluted with petroleum ether: ethyl acetate = 10: 1, 4: 1 to give compound 221a (3 g, 13.9 mmol, yield: 38.9percent) as a yellow solid. Compound 221a: 1H NMR (400mhz, CDCl3 delta 7.43- 7.39 (m, 3h), 7.27 – 7.23 (m, 2h), 7.22 – 7.19 (m, 1h), 7.11 (d, / = 1.0 hz, 1h), 4.22 (q, = 7.2 hz, 2h), 1.24 (t, j = 7.2 hz, 3h).

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

Reference:
Patent; BLADE THERAPEUTICS, INC.; BUCKMAN, Brad, Owen; YUAN, Shendong; ADLER, Marc; EMAYAN, Kumaraswamy; MA, Jingyuang; (687 pag.)WO2018/64119; (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., Safety of Ethyl 1H-imidazole-2-carboxylate

tert-Butyl (2-bromoethyl)carbamate (17.59 g, 78.49 mmol) was added to ethyl 1H- imidazole-2-carboxylate (10 g, 71.36 mmol) and K2CO3 (11.83 g, 85.63 mmol) in DMF (200 mL) under nitrogen and the resulting mixture stirred at 80 C for 8 hours. The reaction mixture was diluted with EtOAc (300 mL), and washed sequentially with water (50 mL x 2). The aqueous layer was then further extracted with EtOAc (50 mL x 5). The combined organic phases were dried over MgS04, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 100% EtOAc in petroleum ether. Pure fractions were evaporated to dryness to afford ethyl 1 -(2-((tert-butoxycarbonyl)amino)ethyl)- lH-imidazole-2-carboxylate (Intermediate 7; 10.7 g, 53%) as a colourless liquid. 1HNMR (400 MHz, DMSO, 21 C) delta 1.20 (3H, t), 1.29 (9H, s), 3.26-3.34 (2H, m) 4.27 (2H, q) ,4.32-4.40 (2H, m), 6.90 (1H, s), 7.06 (1H, s), 7.32 (1H, s).

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

Reference:
Patent; ASTRAZENECA AB; WARD, Richard, Andrew; JONES, Clifford, David; SWALLOW, Steven; GRAHAM, Mark, Andrew; DOBSON, Andrew, Hornby; MCCABE, James, Francis; (223 pag.)WO2017/80979; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference 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.

Example 3A Ethyl 1-[2-(2,4-dichlorophenyl)-2-oxoethyl]-1H-imidazole-2-carboxylate 0.5 g (3.6 mmol) of imidazole-2-carboxylate ethyl were dissolved in 35 ml of acetone, and 0.96 g (3.6 mmol) of 2-bromo-2,4-dichloroacetophenone and 0.49 g (3.6 mmol) of potassium carbonate were added. The mixture was stirred at RT for 12 h. The reaction mixture was concentrated and taken up in water and dichloromethane. The organic phase was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated on a rotary evaporator. The residue was triturated with diethyl ether and the solid was filtered off with suction. This gave 0.9 g (77percent of theory) of the product as a solid. LCMS (method 1): Rt=1.19 min. (m/z=327 (M+H)+) 1H-NMR (400 MHz, DMSO-d6): delta=7.96 (d, 1H), 7.84 (d, 1H), 7.68 (dd, 1H), 7.5 (s, 1H), 7.16 (s, 1H), 5.87 (s, 2H), 4.22 (q, 2H), 3.32 (s, 2H), 1.23 (t, 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; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; US2011/53929; (2011); 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., Product Details of 33543-78-1

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. KH2PO4 solution and the reaction mixture is stirred at rt for 20 h. The reaction mixture is concentrated under reduced pressureand purification of the residue gives the desired product.Example 294 1-[3-(3-ethyl-ureido)-isoquinolin-8-ylmethyl]-1H-imidazole-2-carboxylic acid 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+].

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 33543-78-1.

Reference:
Patent; Bur, Daniel; Gude, Markus; Hubschwerlen, Christian; Panchaud, Philippe; US2013/96119; (2013); A1;,
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 33543-78-1 as follows. category: imidazoles-derivatives

4-Benzylcarbamoyl-2-(ethoxycarbonylimidazolyl)-1-indanone can be prepared in the following way: a mixture of 0.5 g of 4-benzylcarbamoyl-2-bromo-1-indanone, 0.37 g of 2-ethoxycarbonylimidazole and 10 ml of toluene is heated at reflux for 12 hours. The reaction mixture is concentrated on a rotary evaporator. Dichloromethane is added to the evaporation residue, filtration is carried out and the filtrate is washed with distilled water, dried over sodium sulphate and evaporated on a rotary evaporator. The brown oil obtained (0.26 g) is purified by chromatography on a silica column (diameter: 1.5 cm, height: 30 cm), elution being carried out with a dichloromethane/methanol (95/5 by volume) mixture. The foamy product obtained is triturated with 5 ml of ethyl acetate, filtered and the solid is washed with ethyl acetate (2*5 ml) and dried at 50° C. under vacuum (1 mm Hg; 0.13 kPa). 0.07 g of 4-benzylcarbamoyl-2-(2-ethoxycarbonylimidazolyl)-1-indanone is obtained in the form of an orange solid melting at 218° C. 4-Benzylcarbamoyl-2-bromo-1-indanone can be prepared in the following way:

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

Reference 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.

The ethyl 1-(4-cyanomethyl-1-oxoindan-2yl)imidazole-2-carboxylate can be obtained in the following manner: a solution of 1.8 g of ethyl imidazole-2-carboxylate in 30 ml of acetone is supplemented with 8.6 g of potassium carbonate. This suspension is heated at reflux for 15 minutes and then a solution of 3.22 g of 2-bromo-4-(cyanomethyl)indan-1-one in 30 ml of acetone is added. After stirring for 4 hours at reflux temperature, the reaction medium is brought to a temperature close to 20° C. and filtered on sintered glass. The filtrate is evaporated and 2.7 g of a black solid are obtained. The purification by flash chromatography on a silica column (eluent: dichloromethane-ethyl acetate (50-50 by volume)) of this solid gives 0.62 g of ethyl 1-(4-cyanomethyl-1-oxoindan-2-yl)imidazole-2-carboxylate in the form of a brown solid [mass spectrum m/z 309 (M+), 236 ((M-CO2 Et), +), 141 ((C6 H9 N2)+), 68((C3 H4)+)].

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; Rhone Poulenc Rorer S.A.; US5990108; (1999); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. Application In Synthesis of Ethyl 1H-imidazole-2-carboxylate

Description 43; Lambda/-(3-Fluorophenyl)-1-(1W-imidazol-2-ylcarbonyl)-4-piperidinamine (D43); Ethyl imidazole-2-carboxylate (701 mg, 5.0mmol) and D12 (971 mg, 5.0mmol) were dissolved in toluene (25ml) and flushed with argon. This solution was cooled to 00C and treated with trimethylaluminium (7.5ml, 2M solution in hexanes, 15mmol). The mixture was then warmed to 250C and stirred for 16h. The temperature was raised to 500C and the mixture stirred for 4h. The mixture was cooled to 250C and stirred for 3days then treated with Rochelle’s salt (20ml) and stirred for 1h. The resultant solution was poured into water (30ml) and extracted with EtOAc (3x40ml). The combined organics were washed with brine, dried (MgSO4) and concentrated in vacuo. Purification by column chromatography on silica eluting with a 0-10percent MeOH/DCM gradient gave the title compound as a pale yellow solid (775mg). deltaH (CDCI3, 400MHz) 1.50 (2H, m), 2.21 (2H, d), 3.09 (1H, t), 3.58 (2H, m), 3.68 (1H, m), 4.51 (1H1 d), 5.80 (1 H, d), 6.25-6.40 (3H, m), 7.09 (1H, q), 7.12 (1H, s), 7.20 (1H, s), 10.72 (1H, br s). MS (ES): MH+ 289, (M-H+) 287.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 33543-78-1, its application will become more common.

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