Author: Jessica.F

5395-50-6, name is 1,3,4,6-Tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: 1,3,4,6-Tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

In a 50 mL flask equipped with a thermometer, 1.31 g (5.0 mmol) of 1,3,4,6-tetrakis (hydroxymethyl) glycoluril,Pyridine 3.90 g (50.0 mmol)And 25 mL of N, N-dimethylformamide.To the resulting mixture was added, under ice cooling,After 5.33 g (50.0 mmol) of methacryloyl chloride was added dropwise,And the mixture was stirred overnight at room temperature.After this,100 mL of water was added to the obtained reaction mixture,Extraction operation was carried out with 100 mL of ethyl acetate.The obtained organic layer was concentrated under reduced pressure,The obtained concentrate was purified by silica gel chromatography (ethyl acetate / hexane = 1/1 (volume ratio)),733 mg of 1,3,4,6-tetrakis (methacryloyloxymethyl) glycoluril was obtained as a colorless liquid.Yield 27%.

The synthetic route of 5395-50-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SHIKOKU CHEMICALS CORPORATION; KUMANO, TAKESHI; TAKEDA, TAKUMA; MIZOBE, NOBORU; (9 pag.)JP2015/57375; (2015); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 57531-37-0, 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. 57531-37-0, name is 2-Chloro-5-nitroimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 4 Preparation of (S)-2-chloro-1-(2-methyl-2-oxiranylmethyl)-4-nitroimidazole To N,N-dimethylformamide (2.5 ml) solution of (R)-2-methylglycidyl-4-nitrobenzenesulfonate (0.5 g, 96.5percent e.e.) were added 2-chloro-4-nitro-1H-imidazole (0.324 g) and potassium carbonate (0.330 g) at a room temperature. After being stirred the reaction mixture at 50°C for 4 hours, the mixture was cooled to a room temperature, and was poured in water to cease the reaction. Extracted with ethyl acetate, and the extract was washed with water and an aqueous solution being saturated with sodium chloride in this order, then dried over anhydrous magnesium sulfate, and concentrated under a reduced pressure to obtain yellow solid product. The thus obtained yellow solid product was purified by use of a silica gel column chromatography (eluent: n-hexane/ethyl acetate = 7/3), there was obtained (S)-2-chloro-1-(2-methyl-2-oxiranylmethyl)-4-nitroimidazole (0.341 g, yield: 85.6percent) as pale yellow crystals. Melting point: 65.5 – 67.0°C 1H-NMR (CDCl3) delta(ppm): 1.39 (3H, s), 2.62 (1H, d, J=3.6Hz), 2.79 (1H, d, J=3.6Hz), 3.99 (1H, d, J=14.7Hz), 4.38 (1H, d, J=14.7Hz), 7.87 (1H, s). Optical purity: 95.4percent e.e. The optical purity was determined by use of high performance liquid chromatography (HPLC) under the following conditions. Column: CHIRALPAK AD (4.6 mmphi* 250 mm) [manufactured by Daicel Chemical Industries, Ltd.] Moving bed: n-hexane/ethanol = 850/150 Flow velocity: 1.0 ml/minute Detection wave length: 254 nm.

The synthetic route of 2-Chloro-5-nitroimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Otsuka Pharmaceutical Company, Limited; EP1553088; (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 2735-62-8 as follows. category: imidazoles-derivatives

General procedure: 2-(1-Methyl-1H-benzo[d]imidazol-2-yl)acetonitrile (171 mg, 1.0 mmol), t-BuOK (112 mg, 1.0 mmol), and dry THF (5 mL) were stirred for 30 min at room temperature. To the resulting mixture 3-(phenylethynyl)quinoxaline-2-carbonitrile 1a (128 mg, 0.5 mmol) was added by portions. The reaction mixture was stirred for 48 h at room temperature and then evaporated to dryness without heating. The residue was treated with some drops of acetic acid. After evaporation it was mixed with silica gel and purified by flash column chromatography on silica gel (2.5×40 cm) with CHCl3 as the eluent. The first fraction recovered was 1a (32 mg, 25%). The orange fraction was collected and purified additionally by flash column chromatography on Al2O3 (2.5×20 cm) with CHCl3 as the eluent. The orange red fraction with Rf 0.65 gave 5e (48 mg, 24%).

According to the analysis of related databases, 2735-62-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Nguyen, Huong T.L.; Gulevskaya, Anna V.; Pozharskii, Alexander F.; Nelina-Nemtseva, Julia I.; Tetrahedron; vol. 70; 31; (2014); p. 4617 – 4625;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 1003-21-0,Some common heterocyclic compound, 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, molecular formula is C4H5BrN2, 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 43: step b (4-chlorophenyl)(1-methyl-1H-imidazol-5-yl)methanone Ethyl magnesium bromide (3.0 M in diethyl ether, 21.5 mL, 64.4 mmol) was added via syringe over a few minutes to a clear colorless solution of 5-bromo-l -methyl- IH-imidazoie (10.4 g, 64.4 nimol) i THF (100 niL) under a. nitrogen atmosphere in an ice bath, A white precipitate formed during the addition. The mixture was removed from the ice bath and was stirred for 20 minutes, then was again cooled i an ice bath before addition of 4-chloro-N-methoxy-A’r-mefhyibenzamide (10.7 g, 53.6 mmol, Intermediate 43: step a). The resulting white suspension was stirred overnight at room temperature. The reaction was quenched by addition of saturated aqueous NH4CI and diluted with water. The mixture was partially concentrated to remove THF and was diluted with DCM. The mixture was acidified to pH 1 with 1 N aqueous HCl, then neutralized with saturated aqueous NaHC(. The phases were separated and the aqueous phase was further extracted with DCM. The organic extracts were washed with water, then were dried (Na2S0 ), filtered, and concentrated, affording a white solid. The crude product was triturated with a mixture of F,tOAc:heptanes (1 : 1 , 150 ml,). The precipitated solid was collected by vacuum filtration, washing with heptanes, to afford the title compound.

The synthetic route of 1003-21-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; LEONARD, Kristi A.; BARBAY, Kent; EDWARDS, James P.; KREUTTER, Kevin D.; KUMMER, David A.; MAHAROOF, Umar; NISHIMURA, Rachel; URBANSKI, Maud; VENKATESAN, Hariharan; WANG, Aihua; WOLIN, Ronald L.; WOODS, Craig R.; FOURIE, Anne; XUE, Xiaohua; CUMMINGS, Maxwell D.; JONES, William Moore; GOLDBERG, Steven; WO2015/57205; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 13275-42-8, 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. 13275-42-8 name is 2-(2-Bromophenyl)-1H-benzo[d]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.

General procedure: 2-(2-Bromophenyl)benzimidazole (1 mmol), substituted aldehyde (1.2 mmol), NaN3 (1.8 mmol), Cu (10mol%), L-proline (20 mol%), and Cs2CO3 (1 mmol) were added to DMF in a 50 mL round bottom flask, and then the mixture was refluxed at 80 C for 16 h under nitrogen atmosphere. TLC was monitored the reaction till completed, and then the reaction mixture was cooled to room temperature. The mixture was poured into the dichloromethane, washed with brine and water. The organic layer was concentrated with evaporator, and the residue was purified by column chromatography on silica gel to give the target compound (A-4 to A-37).

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

Reference:
Article; Li, Jun-cai; Wang, Ren-xuan; Sun, Yu; Zhu, Jia-kai; Hu, Guan-fang; Wang, Yu-ling; Zhou, Rui; Zhao, Zhong-min; Liu, Ying-qian; Peng, Jing-wen; Yan, Yin-fang; Shang, Xiao-fei; Bioorganic Chemistry; vol. 92; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 1615-14-1, A common heterocyclic compound, 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol, molecular formula is C5H8N2O, 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 3: The synthesis of compound BS-TE-418 Sodium hydride (15 mg, 0.34 mmol) is added to a solution of 5-chloromethyltetrandrine (120 mg, 0.17 mmol) and 1-(2-hydroxyethyl)imidazole (20 mg, 0.25 mmol) in acetonitrile (3 mL). The reaction solution is heated up to 75 C and stirred for 2 hours. Afterwards, the reaction solution is filtered, and the filtrate is concentrated to obtain a crude product, which is then separated and purified with preparative chromatography to give compound BS-TE-418 (20 mg, 18%) as a white solid powder. LC-MS: 1.07min (95.52%), m/z 747 [M+H]+, 374 [1/2 M+H]+. 1H NMR (300 MHz, CD3OD) delta 7.60 (s, 1H), 7.45 (dd, J = 8.4 Hz, 1.8 Hz, 1H), 7.10 (s, 1H), 7.07 (dd, J = 8.4 Hz, 2.7 Hz, 1H), 6.94-6.91 (m, 2H), 6.86 (dd, J = 8.1 Hz, 1.8 Hz, 1H), 6.77 (d, J = 8.4 Hz, 2.4 Hz, 1H), 6.67 (s, 1H), 6.53 (d, 1H), 6.41 (dd, J = 8.1 Hz, 2.1 Hz, 1H), 4.02 (m, 1H), 3.88 (s, 3H), 3.61 (s, 3H), 3.34 (s, 3H), 3.21 (s, 3H), 2.65 (s, 3H), 2.22 (s, 3H).

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; Hangzhou Bensheng Pharmaceutical Co., Ltd.; XU, Rongzhen; RONG, Frank; XIE, Fuwen; LAI, Hongxi; EP2767538; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 641571-11-1, 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. 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 1 Preparation of Nilotinib 4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid (55 gm), 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)-benzenamine (45 gm), diethylcyanophosphonate (63 ml), triethylamine (78 ml) and N,N-dimethylformamide (1100 ml) were added at room temperature. The contents were heated to 60 C. and maintained for 13 hours at 60 C. The reaction mass was then cooled to room temperature and quenched with sodium bicarbonate solution (8%) and ethyl acetate. Then the layers were separated and ethyl acetate layer washed with sodium chloride solution. The separated ethyl acetate layer was then concentrated to obtain a residual solid. To the residual solid was added water (500 ml) and stirred for 30 minutes at room temperature. The separated solid was filtered and dried to obtain a solid. To the solid was added to teterahydrofuran (900 ml) and stirred for 30 minutes at 50 to 55 C. The teterahydrofuran solvent was distilled off under vacuum to obtain a residual solid. To the residual solid was added ethyl acetate (900 ml) and stirred for 1 hour at room temperature. The solid obtained was collected by filtration and dried to obtain 54 gm of nilotinib. Example 2 Preparation of Nilotinib Hydrochloride Crystalline Form H1 [0048] Nilotinib (3 gm) as obtained in example 1 was suspended in ethanol (120 ml) and then heated to reflux. A solution of hydrochloric acid in ethyl acetate (4 ml) was added to the solution at reflux and stirred for 1 hour at reflux. The ethanol solvent was distilled off under vacuum to obtain a residual mass. To the residual mass was added ethyl acetate (50 ml) and then cooled to room temperature. The reaction mass was stirred for 1 hour at room temperature and filtered. The solid obtained was dried to give 3 gm of nilotinib hydrochloride crystalline form H1.

The synthetic route of 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hetero Research Foundation; Reddy, Bandi Parthasaradhi; Reddy, Kura Rathnakar; Reddy, Dasari Muralidhara; Rao, Thungathurthy Srinivasa; Krishna, Bandi Vamsi; US2013/245052; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 760212-58-6, 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. 760212-58-6, name is 1-(4-Bromophenyl)-2-phenyl-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step S101: 2-phenyl-4-N-p-bromophenylbenzimidazole was dissolved in THF (tetrahydrofuran); preferably,In the step, 2-phenyl-4-N-p-bromophenylbenzimidazole was 1. Ommol, THF (tetrahydrofuran)Step S102: cooling to -78 C, adding n-butyllithium, for one hour; preferably, n-butyllithium is 1 · lmmol in this step;Step S103: Diphenylphosphonium chloride is added and the temperature is raised to room temperature for 12 hours. Preferably, diphenylphosphonium chloride is 1.2 mmol in this step;Step S104; adding a methanol quenching reaction while adding 30% H2O2 aqueous solution to give 4- (1-methylbenzimidazolyl) -triphenylphosphine oxide; preferably, 30% H2O2 aqueous solution in this step is 5 ml ; Yield: 70%

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-(4-Bromophenyl)-2-phenyl-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Wuhan Shang Sai Optoelectric Technology Co., Ltd.; Wang Lei; Pan Biao; Wang Bo; Mu Guangyuan; (19 pag.)CN104370964; (2017); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 50995-95-4, A common heterocyclic compound, 50995-95-4, name is 2-Propylimidazole, molecular formula is C6H10N2, 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.

In a 1-L round-bottomed flask, 2-propylimidazole (15.0 g, 136 mmol) and I2 (110 g, 435mmol) were suspended in a mixture of CHCl3 (350 mL) and 2 M NaOH aqueous solution (350mL), and the mixture was stirred at room temperature of 45 h. To this mixture, a saturatedNa2S2O3 aqueous solution until the excess amount of I2 was quenched, the mixture was leftstand until the mixture separate to aqueous and CHCl3 layers. The CHCl3 layer was removedby using dropping funnel, then the aqueous layer was neutralized with acetic acid and asaturated NaHCO3 aqueous solution. The resulting precipitate was collected by filtration andwashed with water, then dried in vacuo at 60 C, to give 11 (43.7 g, 85%) as a soft yellowpowder;

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:
Article; Murata, Tsuyoshi; Yamamoto, Yosuke; Yakiyama, Yumi; Nakasuji, Kazuhiro; Morita, Yasushi; Bulletin of the Chemical Society of Japan; vol. 86; 8; (2013); p. 927 – 939;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 583-39-1, 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. 583-39-1, name is 2-Mercaptobenzimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Benzyl chloride or 1-iodopropane, 89.25 mmol, and potassium carbonate, 170.0 mmol, were added to a solution of 85.0 mmol of 1,3-dihydro-2H-benzimidazole-2-thione in 140 mL of acetone. The mixture was refluxed for 3 h with stirring and poured into water with stirring to dissolve inorganic com-ponents. The precipitate was filtered off and washed with water and methanol. Compound 1b was dried and recrystallized from 20 mL of methanol. Compound 1a required no additional purification. Compound 1a. Yield 93%, colorless crystals, mp 180-181C. 1 H NMR spectrum, delta, ppm: 4.56 s (2H, CH 2 ), 7.07 t (2H, H arom , J = 4.0 Hz), 7.21 t (1H, H arom , J = 6.8 Hz), 7.28 t (2H, H arom , J = 7.2 Hz), 7.35-7.45 m (4H, H arom ), 12.04 br.s (1H, NH). Compound 1b. Yield 55%, colorless crystals, mp 151-152C. 1 H NMR spectrum, delta, ppm: 1.07 t (3H, CH 3 , J = 7.2 Hz), 1.80 sext (2H, CH 2 , J = 6.8 Hz), 3.25 t (2H, CH 2 , J = 7.2 Hz), 7.05 s (2H, H arom ), 7.37 s (1H, H arom ), 12.27 s (1H, NH).

The synthetic route of 2-Mercaptobenzimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kharaneko; Russian Journal of Organic Chemistry; vol. 54; 9; (2018); p. 1363 – 1368; Zh. Org. Khim.; vol. 54; 9; (2018); p. 1350 – 1354,5;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem