Month: May 2021

Application of 342789-81-5, 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. 342789-81-5, name is 1-Butyl-3-methylimidazolium methanesulfonate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

5.1-1-butyl-3-methylimidazolium tetrafluoroborate (BMI.BF4)A mixture formed by 1,3-dimethyl imidazolium methanesulfonate (BMI.CH3SO3) (10.6 g; 45.0 mmol), sodium tetrafluoroborate (6.00 g; 54.5 mmol) and water (5.4 mL) was stirred at room temperature for 30 minutes. The resulting mixture, made up of two phases, was extracted with dichloromethane (3¡Á15 mL). The combined organic extract was dried with anhydrous sodium carbonate and the solvent was evaporated under vacuum and heated (80 C.), which produced the desired BMI.BF4 ionic liquid. (9.35 g; 92% yield).

The synthetic route of 1-Butyl-3-methylimidazolium methanesulfonate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PETROLEO BRASILEIRO S.A. – PETROBRAS; US2008/45723; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 342789-81-5,Some common heterocyclic compound, 342789-81-5, name is 1-Butyl-3-methylimidazolium methanesulfonate, molecular formula is C9H18N2O3S, 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.

5.2-1-butyl-3-methylimidazolium hexafluorophosphate (BMI.BF4)A mixture formed by 1,3-dimethyl imidazolium methanesulfonate (BMI.CH3SO3) (5.80 g; 24.6 mmol), sodium hexafluorophosphate (5.00 g; 29.8 mmol) and water (5.0 mL) was stirred at room temperature for 30 minutes. The resulting mixture, made up by two phases, was extracted with dichloromethane (3¡Á10 mL). The combined organic extract was washed with water (2¡Á20 mL) and dried with anhydrous sodium carbonate. The solvent was evaporated under vacuum and heated (80 C.), which produced the desired ionic liquid BMI.PF6 (6.64 g; 95% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Butyl-3-methylimidazolium methanesulfonate, its application will become more common.

Reference:
Patent; PETROLEO BRASILEIRO S.A. – PETROBRAS; US2008/45723; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 53525-60-3, name is Ethyl 1-trityl-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 53525-60-3, Recommanded Product: Ethyl 1-trityl-1H-imidazole-4-carboxylate

Add 600 mL Methanol and 650 ml tetrahydrofuran to a 5 L dried four-mouth bottle equipped with a mechanical stirring and a thermometer, then add 125 g (0.327mol, 1.0 eq) 1-trityl -1H-imidazole-4-ethyl formate; stir to form a suspension; 1 L sodium hydroxide solution (2M, 6 eq) is dropped into the suspension, wherein the temperature is controlled to be 1020 C. Stir for 5 hrs and then the reaction ends. 1 L Hydrochloric acid solution (2M) is slowly dropped and a great amount of white solids are generated when the mixed solution is stirred. Adjust pH value to 56. Filter and dry to obtain 112 g 1-trityl-1H-imidazole-4-formic acid, with a yield of 96% and a purity of 97% (HPLC).

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; TIANJIN WEIJIE PHARMACEUTICAL CO., LTD; SONG, Honghai; SUN, Zhicun; HUANG, Haiping; ZHANG, Chao; (5 pag.)US2016/272594; (2016); 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. 66247-84-5, name is (1H-Imidazol-4-yl)methanamine hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: (1H-Imidazol-4-yl)methanamine hydrochloride

To the previous mixture containing intermediate a115 (0.44 g, 1.15 mmol, 73 wt percent) is added (1 /-/-imidazol-4-ylmethyl)amine dihydrochloride (0.59 g, 3.46 mmol, 3 eq) [from A. Turner et al., J. Am. Chem. Soc. (1949), 71 , 2801-2803.], and anhydrous cesium carbonate (1.88 g, 5.76 mmol, 5 eq) in dry DMF (15 ml_). The mixture is vigorously stirred at 60 0C for 3 h. The reaction mixture is cooled, concentrated under reduced pressure, diluted with water, and subjected to extraction with ethyl acetate (three times). The combined organic extracts are washed with brine, dried over anhydrous Na2SC>4, and evaporated. The residue (0.35 g) is purified by chromatography on silicagel (gradient CHCI3/MeOH from 20/1 to 10/1 v/v) to afford 5-chloro-2-(1 H-imidazol-4-ylmethyl)-1 ,4- dihydroisoquinolin-3(2H)-one 53 (0.15 g). Yield: 50 percent. LC-MS (MH+): 262/264.

According to the analysis of related databases, 66247-84-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UCB PHARMA S.A.; WO2008/132139; (2008); A2;,
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 70631-93-5 as follows. Product Details of 70631-93-5

To a stirred solution of 4-methyMH-imidazole-2-carboxylic acid (0.50 g) in DMF (20 mL) were added N,Odimethyl hydroxylamine hydrochloride (0.43 g), TEA (1.7 mL) and HATU (1.8 g). The mixture was stirred for 4 hours at 80C and stirred at room temperature for 2 days. The reaction mixture was concentrated in vacuo and the precipitates were filtered out. The filtrate was concentrated in vacuo and the residue was purified with amino-type silica gel chromatography (0″5 % MeOH in CHCI3) to give the title compound (0.41 g, 61 % yield) as pale yellow oil. MS (ESI) m/z : 170 [M+l]. RT = 0.206 min. LCMS condition : A.

According to the analysis of related databases, 70631-93-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD.; TAKASHIMA, Hajime; SASAKI, Toru; TANAKA, Nozomi; OTAKE, Norikazu; TSURUTA, Risa; YAMADA, Yousuke; MATSUDA, Yohei; OGATA, Yuya; (346 pag.)WO2018/216822; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 83279-44-1, The chemical industry reduces the impact on the environment during synthesis 83279-44-1, name is 1H-Imidazol-1-amine hydrochloride, I believe this compound will play a more active role in future production and life.

EXAMPLE 8 1.20 g of 1-aminoimidazole hydrochloride are melted together with 2.70 g of 4-hydroxy-3,5-di-tert.-butylbenzoyl chloride on an oil-bath (about 200-210 bath temperture), whereby a vigorous gas evolution occurs. After 40 minutes, the solid residue is triturated with hot diisopropyl ether and filtered. The filter residue is taken up in water, treated with saturated sodium bicarbonate solution up to an alkaline reaction and extracted three times with methylene chloride. The combined organic extracts are dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure on a rotary evaporator. The residue is taken up in ethyl acetate, heated and the 1-(4-hydroxy-3,5-di-tert.-butylbenzoylamino)imidazole is precipitated while hot with n-hexane. The precipitate is removed by filtration, washed once with n-hexane/ethyl acetate (2:1) and dried at 50 in a high vacuum; m.p. 245 (dec.).

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, 1H-Imidazol-1-amine hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hoffmann-La Roche Inc.; US4908363; (1990); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 109012-23-9, name is Ethyl 1-methyl-4-nitro-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 109012-23-9, COA of Formula: C7H9N3O4

(1) Capping Step After 1-methyl-4-nitroimidazole-2-carboxylic acid ethyl ester (2.56 g, 12.85 mmol) was dissolved in EA (20 ml), 10% Pd/C (100 mg, catalytic weight) was added thereto. The mixture was stirred for 10 hours at room temperature under hydrogen atmosphere to reduce a nitro group (NO2) into an amino group (NH2), whereby an imidazole-type amino acid was obtained. 10% Pd/C was filtered out by celite 545 filter, and the filtrate was washed with EA and MeOH, and concentrated. To the residue were added carbonic acid 4-nitro-phenyl ester 2-(4-trifluoromethyl-phenylsulfanyl)-ethyl ester (4.52 g, 11.67 mmol) dissolved in anhydrous DCM (40 ml), DIEA (4.06 ml, 23.32 mmol), DMAP (2.85 g, 23.32 mmol), and HOBt (3.57 g, 23.32 mmol), and the mixture was stirred at room temperature. After 12 hours have passed, the reaction was stopped by adding water and the reaction mixture was extracted with DCM. The organic layer was dried over anhydrous MgSO4 and concentrated. The residue was purified by silica gel column chromatography (EA/n-hexane=1/2, v/v) to give 1-methyl-4-[2-(4-trifluoromethyl-phenylsulfanyl)-ethoxycarbonylamino]-1H-imidazole-2-carboxylic acid ethyl ester (3.77 g, 77.40%) of a white solid. TLC (EA/n-hexane=1/2) Rf: 0.14 1H NMR (CDCl3) delta 7.54 (d, J=8.4 Hz, 2H), 7.45 (d, J=8.1 Hz, 2H), 7.31 (brs, 1H), 7.23 (s, 1H), 4.40 (q, J=6.9 Hz, 3H), 4.33 (t, J=7.2 Hz, 2H), 4.00 (s, 3H), 3.26 (t, J=6.9 Hz, 2H), 1.41 (t, J=7.1 Hz, 2H) 13C NMR (CDCl3) 158.50, 152.57, 140.52, 136.92, 131.58, 129.27, 128.33, 127.89, 127.67, 127.46, 127.03, 125.79, 125.75, 125.70, 125.65, 122.07, 118.47, 113.15, 63.33, 61.48, 36.05, 31.10, 14.39

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Han, Hogyu; Jeong, Nakcheol; Lee, SangJo; Oh, Jin Gab; Yu, Hosung; US2003/220469; (2003); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 109012-23-9, 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. 109012-23-9, name is Ethyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

Im-2 (0.4 g) in ETOH/ETHYL acetate (1: 1,14 mL) and Pd/C (10%, 0.3 g) were stirred under a slight positive pressure of hydrogen (ca 1.1 atm) for 3-4 hr. The reaction mixture was filtered using celite and solvent evaporated on the rotary. The remaining solid was freeze dried to yield a slightly yellow product. Yield (0.38 g, 95%). 1H NMR (DMSO): 8 6.45 (s, 1H), 4.5 (bs, 2H, NH2), 4.2 (q, 2H, J=7 Hz), 3.76 (s, 3H), 1.24 (t, 3H, J=7. 9 Hz).

The chemical industry reduces the impact on the environment during synthesis Ethyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; UNIVERSITY OF WESTERN SYDNEY; WO2005/33077; (2005); 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 670-95-1 as follows. Quality Control of 4-Phenylimidazole

3.04 g (20 mmol) of 4-(hydroxymethyl)phenylboronic acid, 1.44 g (10 mmol) of 4-phenylimidazole, 2.8 ml (20 mmol) of triethylamine and 1.64 ml (20 mmol) of pyridine are dissolved in 20 ml of dimethylformamide. 2.72 g (15 mmol) of copper diacetate are added and the mixture is stirred for 24 hours at ambient temperature. It is diluted with 200 ml of dichloromethane and 200 ml of aqueous 28% ammonia solution. After the phases have settled and been separated, the aqueous phase is extracted with 100 ml of dichloromethane. The organic phases are washed with 50 ml of saturated aqueous sodium chloride solution, dried over sodium sulphate and evaporated to dryness. The product is purified by chromatography on silica gel, eluting with a 97/3 then 95/5 mixture of dichloromethane and methanol. The product is recrystallized from a mixture of toluene and diisopropyl ether, to give 1.82 g of product in the form of white crystals. Melting point ( C.): 137-139

According to the analysis of related databases, 670-95-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sanofi-Aventis; US2006/14830; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 378203-86-2, These common heterocyclic compound, 378203-86-2, name is Ethyl 1-methyl-4-nitro-1H-pyrazole-3-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.

INTERMEDIATE 13 Ethyl 4-amino-i -methylpyrazole-3 -carboxylateTin(II) chloride dihydrate (7.42 g, 32.9 mmol) was added to a solution ofIntermediate 12 (i.3i g, 6.58 mmol) in EtOH (50 mL). The reaction was heated at 50Cwith stirring for 3.5 h, then cooled to room temperature and concentrated in vacuo. The residue was diluted with DCM and treated with 2M aqueous NaOH solution. A viscous thick precipitate formed. The mixture was filtered through celite, and the two layers were separated. The aqueous layer was extracted with DCM (twice). The combined organiclayers were passed through a phase separator cartridge, then evaporated. The resulting crude material was purified by silica gel chromatography (gradient 25-75% EtOAc in isohexane). The title compound (0.32 g, 29%) was isolated as a dark blue/black oil. oH (400 MHz, DMSO-d6) 7.i2 (s, iH), 4.66 (s, 2H), 4.23 (q, 2H,J7.i Hz), 3.76 (s, 3H), i.27 (t, 3H,J7.i Hz).

Statistics shows that Ethyl 1-methyl-4-nitro-1H-pyrazole-3-carboxylate is playing an increasingly important role. we look forward to future research findings about 378203-86-2.

Reference:
Patent; FORD Daniel James; HUANG Qiuya; NEUSS Judi Charlotte; REUBERSON James Thomas; VANDERHOYDONCK Bart; WO2015/193168; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem