Author: Jessica.F

35203-44-2, 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 35203-44-2 as follows.

Take a 100 mL two-necked flask, add N-propyl imidazole (2.64 g, 18.0 mmol), 35 mL toluene,3-Bromopropylphenylethoxyphosphine oxide (6.26 g, 20.0 mmol) was added dropwise with heating and stirring;The reaction was performed at 85¡ãC for 6 h and cooled to room temperature. Pour out the upper toluene,Add 100mL of deionized water to dissolve the product to obtain an aqueous phase.The aqueous phase was washed with an EtOAc_PE=3:1 organic phase (30 mL x 4) to separate the aqueous phase two;Di(2-ethylhexyl)phosphate (P204) (5.60 g, 18.0 mmol) was refluxed under the action of sodium for 24 h.The resulting sodium salt was dissolved in dichloromethane and the previously separated aqueous phase was stirred at room temperature for 3 h.Add 50 mL of CH2Cl2 and stir to separate the organic phase. Wash the organic phase with deionized water (20 mL x 5)Separate the organic phase two, add anhydrous Na2SO4 to dry the organic phase two, filter,The majority of CH2Cl2 was evaporated under reduced pressure and dried under vacuum at 70¡ã C. for 3 h to give 12.50 g of pale yellow viscous liquid (94percent yield).

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

Reference:
Patent; Ningbo University; Wang Junping; Liang Hongze; Feng Da; Zhao Jieying; Kang Xinchun; Zhang Xiaozhen; Shen Fei; Huang Feilong; (21 pag.)CN104945435; (2018); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

The chemical industry reduces the impact on the environment during synthesis 51605-32-4, name is Ethyl 5-methyl-1H-imidazole-4-carboxylate, I believe this compound will play a more active role in future production and life. 51605-32-4

a) 4-methylimidazole-5-carboxylic Acid Following the procedure of Example 1(g), except substituting ethyl 4-methylimidazole-5-carboxylate for N-(4-pyridinylmethoxycarbonyl)-L-leucine methyl ester, the title compound was prepared as a white solid (0.428 g, 52%). MS (ESI): 126.8 (M+H)+.

The chemical industry reduces the impact on the environment during synthesis 51605-32-4. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Halbert, Stacie Marie; Michaud, Evelyne; Thompson, Scott Kevin; Veber, Daniel Frank; US2002/49316; (2002); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding some certain compound to certain chemical reactions, such as: 827-43-0, name is 4-Methyl-2-phenyl-1H-imidazole, 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 827-43-0. 827-43-0

To a solution of 4-methyl-2-phenylimidazole (111, 15.8 g) in dimethylformamide (100 ml) is added sodium hydride. (4.4 g, 60% in mineral oil) in small portions. After the addition is complete, the mixture was stirred for an additional 20 min and treated with 1-iodobutane (18.8 g). The reaction is fitted with a reflux condensor and heated at 100 C. for 12 h. The cooled reaction mixture is partitioned between water (300 ml) and diethyl ether (300 ml). The organic layer is washed with water (3¡Á200 ml), dried (Na2SO4) and concentrated to provide 20.5 g of N-butylimidazoles. Analysis by 1H-NMR and GC-MS revealed mixture of 1-butyl-2-phenyl-4-methylimidazole (112) and 1-butyl-2-phenyl-5-methylimidazole in a ratio of 11.5/1. The mixture was carried on to the next step without purification.

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 4-Methyl-2-phenyl-1H-imidazole.

Reference:
Patent; Neurogen Corporation; US6723743; (2004); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 1849-01-0, name is 1-Methyl-1H-benzo[d]imidazol-2(3H)-one, 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 1849-01-0, 1849-01-0

To a stirred solution of l-methyl-2,3-dihydro-lH-l,3-benzodiazol-2-one (217 mg, 1.46 mmol) in DMF (2 mL) was added NaH (64.5 mg, 1.61 mmol, 60% w/w dispersed into mineral oil) at 0 C under nitrogen atmosphere. The reaction mixture was stirred for 20 min at 0 C. To the above mixture was added dropwise a solution of 3-bromopiperidine-2,6-dione(140.6 mg, 0.73 mmol) in DMF (0.5 mL) at 0 C. The resulting mixture was stirred for additional 3 hours at room temperature. The resulting mixture was quenched with AcOH (0.5 mL) and was concentrated under reduced pressure. The crude product was purified by prep-HPLC with the following conditions: Column: XBridge Shield RP18 EVO Column, 5 um, 19 x 150 mm; Mobile Phase A: water (plus 0.05% FA), Mobile Phase B: ACN; Flow rate: 20 mL/min; Gradient: 10% B to 35% B in 7 min; Detector: UV 220 nm; Rt: 6.30 min. Desired fractions were collected and concentrated under reduced pressure. The residue was lyophilized to afford 3-(3-methyl-2-oxo-2,3-dihydro-lH- l,3-benzodiazol-l-yl)piperidine-2,6-dione, 1-2, as a white solid (30.4 mg, 21%): NMR (400 MHz, OMSO-d6) delta 11.03 (br s, 1H), 7.13 – 6.97 (m, 4H), 5.30 (dd, J= 12.7, 5.4 Hz, 1H), 3.35 (s, 3H), 2.90 – 2.78 (m, 1H), 2.73 – 2.49 (m, 2H), 2.03 – 1.90 (m, 1H); LC/MS (ESI, m/z): [(M + 1)]+ = 260.2.

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-Methyl-1H-benzo[d]imidazol-2(3H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KYMERA THERAPEUTICS, INC.; MAINOLFI, Nello; JI, Nan; ZHANG, Yi; WEISS, Matthew M.; (223 pag.)WO2019/60693; (2019); 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. 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, This compound has unique chemical properties. The synthetic route is as follows., 641571-11-1

To a solution of 2- (5-ethoxy-6-oxo-1 6-dihydropyridin-3-yl) -4 6-dimethylpyrimidine-5-carboxylic acid (150 mg 0.519 mmol) 3- (4-methyl-1H-imidazol-1-yl) -5- (trifluoromethyl) aniline (125 mg 0.519 mmol) and Et3N (79 mg 0.778 mmol) in 1 4-dioxane (5 mL) stirred under N2at 20 was added DPPA (171 mg 0.622 mmol) in one charge. The reaction mixture was heated to 80 for 1 hr. Then the solution was concentrated. The residue was purified by preparative HPLC (Instrument DC/Column ASB C18 150*25mm/Mobile phase A Water+0.1HCl/Mobile phase BMeCN /Flowrate 25 mL/min /Gradient Profile Description 15-55 (B) ) to yield a off white solid of 1- (2- (5-ethoxy-6-oxo-1 6-dihydropyridin-3-yl) -4 6-dimethylpyrimidin-5-yl) -3- (3- (4-methyl-1H-imidazol-1-yl) -5- (trifluoromethyl) phenyl) urea dihydrochloride (11.53 mg 3.67) . TLC (DCM/MeOH 51 Rf 0.4) 1HNMR(400 MHz CD3OD) delta9.44-9.40 (m 1H) 8.27-8.23 (m 1H) 8.20 (s 1H) 7.92 (s 2H) 7.84 (s 1H) 7.69 (s 1H) 4.17 (d J 6.8 Hz 2H) 2.57 (s 6H) 2.44 (s 3H) 1.48 (t J 6.9 Hz 3H) ES-LCMS m/z 528.2 (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; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; GLAXOSMITHKLINE (CHINA) R & D COMPANY LIMITED; CHEUNG, Mui; DEMARTINO, Michael P.; EIDAM, Hilary Schenck; GUAN, Huiping Amy; QIN, Donghui; WU, Chengde; GONG, Zhen; YANG, Haiying; YU, Haiyu; ZHANG, Zhiliu; (391 pag.)WO2016/37578; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

15965-54-5, 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 15965-54-5 as follows.

General procedure: A mixture of 10 (5 mM), 11 (5 mM) in DMF (20 mL) containing K2CO3 (2 mM) and TBAB (2 mM) was stirred at RT for a period of 3-5 h. The reaction was monitored by TLC analysis. After the completion of reaction, the mixture was poured into ice-cold water (30 mL). The separated solid was filtered, washed with water (2 9 10 mL) and dried. The crude product was recrystallized from a suitable solvent to yield pure 9.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 15965-54-5, and friends who are interested can also refer to it.

Reference:
Article; Srikrishna, Devulapally; Dubey, Pramod Kumar; Research on Chemical Intermediates; vol. 44; 7; (2018); p. 4455 – 4468;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

496-46-8, Adding some certain compound to certain chemical reactions, such as: 496-46-8, name is Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, 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 496-46-8.

14.2 g (100 mmol) of glycoluril,16.0 g (400 mmol) of sodium hydroxide and 140 mL of dimethylsulfoxide were mixed,After heating and stirring at 40 C. for 1 hour, And 34.4 g (400 mmol) of allyl chloride were added dropwise at the same temperature over 20 minutes, and the mixture was heated and stirred at 40 C. for 2 hours to complete the reaction.The resulting reaction mixture was evaporated to dryness under reduced pressure, and the obtained dry solid was separated and extracted with 400 mL of ethyl acetate and 400 mL of water, and the ethyl acetate layer was washed with 100 mL of water, then with 100 mL of saturated brine, Dried over sodium sulfate, and ethyl acetate was distilled off under reduced pressure to obtain 27.4 g of 1,3,4,6-tetraallyl glycoluril as a colorless oil, yield 90%.

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 496-46-8.

Reference:
Patent; Shikoku Chemicals Co., Ltd.; Takeda, Takuma; Kashihara, Takashi; Kumano, Noboru; Mizobe, Noboru; (59 pag.)JP2015/59101; (2015); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 1849-01-0 name is 1-Methyl-1H-benzo[d]imidazol-2(3H)-one, 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. 1849-01-0

Step A: 5-(3-Methyl-2-oxo-2,3-dihydro-benzoimidazol-1-yl)-thiazolidine-2,4-dione (I-51). To a solution of 1-methyl-1,3-dihydro-benzoimidazol-2-one (300 mg, 1.13 mmol) in DMF (4.0 mL) was added NaH (60% in mineral oil, 101.7 mg, 3.39 mmol) at 0 oC under nitrogen. The reaction mixture was stirred at 0 oC under N2 for 30 minutes. Then 5-bromo-thiazolidine-2,4- dione (230 mg, 1.13 mmol) in DMF (1 mL) was added slowly. After stirring at r.t. for 10 minutes, the reaction was quenched with water (30 mL) and extracted with EtOAc (50 mL x 3). The combined organic layer was washed with brine and dried over Na2SO4. The mixture was filtered and the filtrate solvent was removed under reduced pressure. The residue was purified via silica gel column chromatography (Petroleum ether/EtOAc) to give the title compound (22 mg, 7.4% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) delta ppm: 12.7 (s, 1H), 7.76-7.13 (m, 5H), 3.34 (s, 3H). LC-MS: Calculated exact mass = 263.0; Found [M+H]+ = 263.9.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Methyl-1H-benzo[d]imidazol-2(3H)-one, and friends who are interested can also refer to it.

Reference:
Patent; KYMERA THERAPEUTICS, INC.; MAINOLFI, Nello; JI, Nan; KLUGE, Arthur F.; (282 pag.)WO2019/140387; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1615-14-1, Adding a certain compound to certain chemical reactions, such as: 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol, 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 1615-14-1.

A 50-mL three-necked, round-bottomed flask, equipped with thermometer, nitrogen inlet, addition funnel, magnetic stirrer and reflux condenser was flame dried and flushed with nitrogen. The flask was charged with 25 ml_ of anhydrous dichloromethane. Freshly distilled 1-ethanol imidazole (1, 0.01 mol) was added into the flask. The flask was chilled with ice-water bath and benzyl chloride (0.011 mol) in 15 ml_ of anhydrous dichloromethane was added cautiously into the flask with continous stirring over 20 minutes. The solution was heated under reflux for 5 hours and then allowed to cool to room temperature. The dichloromethane solvent was distilled under to give 92% of 3-benzyl-1-ethanol imidazolium chloride 5.

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, 2-(1H-Imidazol-1-yl)ethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MIMOS BERHAD; AHMAD, Mohd Rais; WO2010/33014; (2010); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1546-79-8, 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 1546-79-8 as follows.

5-[4-Fluoro-5-(4-bromophenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]-2-pyridinesulfonamide (Step 2) To a solution of 1-(4-bromophenyl)-2-fluoro-1-ethanone (3.54 g, 16.3 mmol) in tetrahydrofuran (50 ml) was added dropwise 1M lithium hexamethyldisilazide tetrahydrofuran solution (19.6 ml, 19.6 mmol) at -78 C. After stirring for 45 min., N-trifluoroacetylimidazole (2.3 ml, 19.6 mmol) was added. The resulting mixture was allowed to warm up to room temperature and stirred for 1.5 hr. The mixture was acidified with 2M hydrochloric acid and extracted with diethyl ether (300 ml). The separated organic layer was washed with water (100 ml*3) and dried over magnesium sulfate. The solution was evaporated to give 5.2 g of 1-(4-bromophenyl)-2,4,4,4-tetrafluoro-1,3-butanedione as a brown oil.

According to the analysis of related databases, 1546-79-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; US2003/144280; (2003); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem