Author: Jessica.F

Adding a certain compound to certain chemical reactions, such as: 20970-50-7, name is 1-(1-Methyl-1H-imidazol-5-yl)ethanone, 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 20970-50-7, Safety of 1-(1-Methyl-1H-imidazol-5-yl)ethanone

EXAMPLE 3 2-Benzyl-4-(1′-methyl-5′-imidazolyl)thiazole hydrochloride A solution of 5-acetyl-1-methylimidazole (100 mg, 0.81 mmol) in 2.4 ml of acetic acid was stirred at 25 C. as 0.24 ml (0.30 g, 1.2 mmol) of 31% hydrobromic acid in acetic acid was added. Pyridinium bromide perbromide (0.29 g, 0.91 mmol) was added, giving an orange solution from which a yellow precipitate formed after 30 minutes. After 2.5 hours, ether (5 ml) was added. The supernatant was removed by pipet, and the precipitate was dried under a stream of nitrogen. Ethanol (6 ml) and benzylthioamide (137 mg, 0.91 mmol) were added, and the mixture was heated to reflux for 45 minutes. The reaction was cooled to 25 C., poured into 25 ml of ether, and washed with 50 ml of 1.25N aqueous sodium hydroxide. The aqueous layer was extracted with 2*25 ml of ether, and the organic extracts were combined, dried (sodium sulfate), filtered, and evaporated. The residue was purified by column chromatography on silica gel (5 g), eluted with 8% isopropanol in 4:1 dichloromethane/ethyl acetate, yielding 2-benzyl-4-(1′-methyl-5′-imidazolyl)thiazole (159 mg, 77% yield) as an almost colorless oil. The free base (159 mg, 0.62 mmol) was dissolved in 10 ml of methanol and treated with 0.32 ml (0.64 mmol) of 2.0N aqueous hydrochloric acid. Evaporation of the solution yielded 183 mg of pale yellow crystals. Recrystallization from 2:1 ethyl acetate/ethanol gave 2-benzyl-4-(1′-methyl-5′-imidazolyl)thiazole hydrochloride (111 mg, 61% recovery) as colorless plates, m.p. 191-194 C.

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, 1-(1-Methyl-1H-imidazol-5-yl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Merck & Co., Inc.; US4746669; (1988); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 50995-95-4, name is 2-Propylimidazole, 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 50995-95-4, category: imidazoles-derivatives

Taking 2 – propyl imidazole 11.0g (0.1 muM), KOH 8.4g (0.15 muM), K2CO313 . 8g (0.1 muM) and tetrabutyl ammonium bromide 1.6g (0.005 muM) dissolved in 75 ml dichloromethane in, room temperature stirring 0.5h after, slow instillment bromine ethyl acetate 0.1 muM (11.2 ml), dropwise, 39 C reflow 9h, filtering, saturated salt water washed filtrate three times, dried with anhydrous sodium sulfate, 25 C distilling the organic phase to liquid droplet not to trickle out, obtaining oil object, to obtain the compound IV intermediate 1

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

Reference:
Patent; Jiangsu Atomic Medical Institute; Qiu Ling; Lin Jianguo; Lv Gaochao; Li Ke; Peng Ying; Luo Shineng; Wang Shanshan; Zhao Xueyu; (27 pag.)CN106749406; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 14741-71-0, A common heterocyclic compound, 14741-71-0, name is Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate, molecular formula is C11H12N2O2, 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.

General procedure: LHMDS (1.65 mL, 1 M in THF, 1.65 mmol, 5.0 equiv) was added dropwise to a solution of ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate (67.6 mg, 0.33 mmol, 1.0 equiv) and 1-(4-methoxybenzy-l)-1H-thieno[2,3-d][1,3]oxazine-2,4-dione (0.33 mmol, 1.0 equiv) in anhydrous THF (15 mL) at -78 C. The resulting solution was slowly warmed to room temperature and then stirred overnight at 80 C. After the reaction completed, quenched with a small amount of NH4Cl (aq, satd). And then concentrated in vacuo, the resulting crude material was purified by column chromatography (petroleum ether/ethyl acetate/acetic acid = 500:100:20, v/v/v) on silica gel to afford the product as a white solid.

The synthetic route of 14741-71-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Song, Pinrao; Peng, Peng; Han, Mengmeng; Cao, Xianchao; Ma, Xiaodong; Liu, Tao; Zhou, Yubo; Hu, Yongzhou; Bioorganic and Medicinal Chemistry; vol. 22; 17; (2014); p. 4882 – 4892;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 33016-47-6, These common heterocyclic compound, 33016-47-6, name is 1-Trityl-1H-imidazole-4-carbaldehyde, 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.

Example 2Preparation of 2-(1-trityl-1 H-imidazole-4-yl)indan-1 ,3-dione 1-Trityl-1 H-imidazole-4-carboxaldehyde (12Og, 0.319mol) and phthalide (42.8g, 0.319mol) were added to stirred ethyl acetate (100OmL) in a 4-neck round bottom flask fitted with a mechanical stirrer, a thermometer, a dropping funnel and a reflux condenser.Meanwhile sodium methoxide (51.7g, 0.957mol) was added to cooled methanol (50OmL) in a separate vessel. Thereafter the methanolic solution of sodium methoxide was added to the reaction mixture at 6O0C and was heated at this temperature for 3 hours and then cooled to 3O0C, at which point the solvent was removed by distillation at a reduced pressure.The distillation residue was poured into water and aqueous hydrochloric acid solution was added, until pH=4-5. The solid orange-brownish precipitates were filtered, the crude product of 2-(1-trityl-1 H-imidazole-4-yl)indan-1 ,3-dione was washed on filter with water.After the recrystallization of crude 2-(1-trityl-1 H-imidazole-4-yl)indan-1 ,3-dione from ethanol the yield of the 2-(1-trityl-1 H-imidazole-4-yl)indan-1 ,3-dione intermediate product was 97.4g (67.2%), having a melting temperature of 213 to 215C

Statistics shows that 1-Trityl-1H-imidazole-4-carbaldehyde is playing an increasingly important role. we look forward to future research findings about 33016-47-6.

Reference:
Patent; Grindeks, a joint stock company; WO2009/71584; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 1457-58-5,Some common heterocyclic compound, 1457-58-5, name is 2-Methyl-1H-imidazole-5-carboxylic acid, molecular formula is C5H6N2O2, 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.

Scheme 96. The imidazole-acid (2 g, 12.3 mmol) was taken up in 4 M HCI in dioxane (10 mL) and EtOH (120 mL) and heated at 90 0C for 18 h. The solution was concentrated. The residue was partitioned between EtOAc and sat. NaHCO3 (aq.). The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine and dried (MgSO4). The solution was filtered which provided 1.2 g (63 %) of the imidazole-ester as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Methyl-1H-imidazole-5-carboxylic acid, its application will become more common.

Reference:
Patent; SCHERING CORPORATION; WO2009/5646; (2009); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 18075-64-4,Some common heterocyclic compound, 18075-64-4, name is 1-Phenyl-1H-imidazole-4-carboxylic acid, molecular formula is C10H8N2O2, 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.

Example 185 Synthesis of 1-Phenyl-1H-imidazole-4-carboxylic acid {2-[4-(2,5-difluoro-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide DIPEA (170 mg, 1.3 mmol) was added to a stirred solution of 1-phenyl-1H-imidazole-4-carboxylic acid (55 mg, 0.29 mmol) in DMF (5 mL) followed by HOBt (43 mg, 0.32 mmol) and EDCI (140 mg, 0.7 mmol). After 2 minutes of stirring, 2-amino-1-[4-(2,5-difluoro-phenoxy)-piperidin-1-yl]-ethanone hydrochloride (prepared according to Step 1 and 5 of the General Scheme) (98.5 mg, 0.32 mmol) was added and the resulting mixture was stirred at ambient temperature overnight. The reaction mixture was diluted with cold water, extracted with ethyl acetate, dried over sodium sulfate and concentrated under reduced pressure. The residue obtained was purified by washing with ether to afford 63.5 mg (49.6% Yield) of 1-phenyl-1H-imidazole-4-carboxylic acid {2-[4-(2,5-difluoro-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 441.17. 1H NMR (300 MHz, DMSO-d6): delta 8.4 (s, 1H), 8.3 (s, 1H), 8.08 (t, 1H), 7.8 (d, 2H), 7.6 (t, 2H), 7.44 (t, 1H), 7.3 (m, 1H), 6.84 (m, 1H), 4.8 (m, 1H), 4.2 (d, 2H), 4.0 (bs, 1H), 3.8 (bs, 1H), 3.7 (bs, 2H), 3.5 (bs, 1H), 2.1 (t, 2H), 1.8 (d, 2H).

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

Reference:
Patent; Forest Laboratories Holdings Limited; US2009/239810; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 2466-76-4, 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. 2466-76-4 name is 1-(1H-Imidazol-1-yl)ethanone, 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.

General procedure: Nucleoside/nucleotide (2; 100 mM) and N-acetyl imidazole (1a;10 equiv) were dissolved in water (pH 8; adjusted with 4 MNaOH). The solution was incubated at r.t. for 4 h, and NMR spectra were periodically acquired. The product was purified byreverse-phase (C18) flash coumn chromatography (eluted at pH4 with 100 mM NH4HCO2/MeCN = 98:2 to 80:20). The fractions containing 5 were lyophilised to yield a white powder.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(1H-Imidazol-1-yl)ethanone, and friends who are interested can also refer to it.

Reference:
Article; Fernandez-Garcia, Christian; Powner, Matthew W.; Synlett; vol. 28; 1; (2017); p. 78 – 83;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 36947-68-9, 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. 36947-68-9 name is 2-Isopropyl-1H-imidazole, 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.

To a solution of ethyl 4-chloropyrimidine-5-carboxylate (10.5g, 0.056mol) was dissolved in DMF (lOOmL) was added 2-isopropyl-lH-imidazole (6.2g, 0.056mol) and Cs2C03 (27.6g), and then heated to 80C for lhrs, showed reaction completed). After cooled to r.t., water (500 mL) was added, then extracted with EA (200 mL* 2), washed with brine and dried over Na2S04. Then concentrated under reduced pressure and purified by flash chromatography on silica gel column (elution: PE/EA=3/1) to giveExample 43a (9.7 g, yield 66%) as a yellow solid. LCMS [M+1] =261

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

Reference:
Patent; FRONTHERA U.S. PHARMACEUTICALS LLC; JIN, Bohan; DONG, Qing; HUNG, Gene; (212 pag.)WO2017/218960; (2017); 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 10040-98-9 as follows. category: imidazoles-derivatives

General procedure: A mixture of azolyl ketone (1a/1b) (1 mmol) and aryloxy benzaldehyde (2a-f) (1 mmol) were dissolved in 10% NaOH-EtOH (5 mL), it was stirred at room temperature for 9-10 h. After completion, 5 mL water was added to the reaction mixture. The separated solid compound was filtered and washed with water. It was purified by crystallization with methanol/chloroform or basic alumina column chromatography to give the desired compounds (3-13).The compounds (16-31) were prepared by the reaction of their corresponding aldehyde and ketone partners.

According to the analysis of related databases, 10040-98-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Marrapu, Vijay K.; Chaturvedi, Vinita; Singh, Shubhra; Singh, Shyam; Sinha, Sudhir; Bhandari, Kalpana; European Journal of Medicinal Chemistry; vol. 46; 9; (2011); p. 4302 – 4310;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 2620-76-0, These common heterocyclic compound, 2620-76-0, name is 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, 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.

General procedure: The solution of n-BuLi in 2.5Mn-hexane (2.64 mL,6.6 mmol)was added dropwise to a solution of 2-(4-bromophenyl)-1-phenyl-1H-benzo[d] imidazole (2.09 g, 6 mmol) in dry THF(30 mL) at 78 C. At temperature of 78 C, the resulting reactionmixture was stirred continuously. Thereafter, we slowly added trimethylchlorosilane(0.76 mL, 6 mmol) to the mixture. Then, thereaction temperature was allowed to warm at room temperatureand stirred overnight. The reaction was quenched by adding water, and the crude product was extracted twice using 100 mL ofdichloromethane. Finally, the crude productwaswashed with brine.The combined organic layer was dried over MgSO4 and subjected tofiltration. The filtrates were dried under reduced pressure, and theresidue was subjected to column chromatography using ethyl acetate/n-hexane (v:v 1:10) as an eluent. Compound 1 was obtainedas a white solid with yield of 78%. We could not perform train sublimationof compound 1 due to its poor thermal stability.

The synthetic route of 2620-76-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yi, Seungjun; Kim, Jin-Hyoung; Bae, Woo-Ri; Lee, Jiwon; Han, Won-Sik; Son, Ho-Jin; Kang, Sang Ook; Organic electronics; vol. 27; (2015); p. 126 – 132;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem