Author: Jessica.F

Synthetic Route of 1964-77-8, 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. 1964-77-8, name is 5-Bromo-2-methyl-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To 5-bromo-2-methylbenzimidazole (38 g, 180 mmol) in TEtaF (400 mL) was added di-tert-butyl dicarbonate (39 g, 189 mmol). The reaction mixture was stirred at room temperature for 24 h and then concentrated. Ethyl acetate (400 mL) was added to the residue, and the solution was washed with 10% aqueous citric acid (2 x 100 mL), water (100 mL), and brine (100 mL), dried over sodium sulfate, and concentrated. Column chromatography on silica (gradient 20-30% ethyl acetate in hexane) provided 1,1 -dimethyl 6-bromo-2-methyl-lH- benzimidazole-1-carboxylate (27 g, 48% yield) as a beige solid. MS (EI) for Ci3Hi5BrN2O2: 312 (MH+)

The synthetic route of 5-Bromo-2-methyl-1H-benzo[d]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EXELIXIS, INC.; AAY, Naing; BLAZEY, Charles, M.; BOWLES, Owen, Joseph; BUSSENIUS, Joerg; CURTIS, Jeffry, Kimo; DEFINA, Steven, Charles; DUBENKO, Larisa; HARRIS, Jason, R.; JACKSON-UGUETO, Eileen, E.; KIM, Angie, Inyoung; MANALO, Jean-claire, Limun; PACK, Michael; PETO, Csaba, J.; RICE, Kenneth, D.; TSANG, Tsze, H.; WANG, Longcheng; WO2010/138490; (2010); 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. 3034-50-2, name is Imidazole-4-carbaldehyde, A new synthetic method of this compound is introduced below., Recommanded Product: 3034-50-2

First, 4-imidazole formaldehyde (1a, 960 mg, 10 mmol) was added to the reaction flask.Place in ice water bath. After 10min,Add triethylamine (TEA) (278 mul, 2.0 mmol) to the reaction flask,The mixture was stirred in an ice-water bath for 5 min.Di-tert-butyl dicarbonate (2.4 g, 1.0 mmol) was then added to the reaction flask.The reaction was moved to room temperature and reacted overnight. After the reaction was detected by TLC, the solvent was spin-dried.Alumina column chromatography (PE: EA = 2: 1) gave Intermediate 1b.

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; Xihua University; Wang Zhouyu; Qian Shan; Yang Lingling; Li Ling; Xu Wei; Yang Huan; Liu Siyan; Yao Hao; Yan Jie; Li Chao; (23 pag.)CN110294714; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 1219741-19-1, 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. 1219741-19-1 name is 5-Chloro-6-iodo-2-(methylsulfonyl)-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.

To a suspension of 6-chloro-5-iodo-2-(methylsulfonyl)-lH-benzo[d]imidazole (5.042 g, 14.14 mmol) in DCM (100 mL) at 0C was added TEA (2.96 mL, 21.21 mmol), and SEM-C1 (2.76 mL, 15.55 mmol) dropwise. The resulting solution was stirred from 0C for 1 hr. The reaction mixture was partitioned between water (200 mL) and DCM (100 mL), the aqueous phase was extracted with DCM (200 mL), and the combined organic phase was dried over anhydrous Na2S04, concentrated and the residue was purified on silica gel column using EtOAc/hexane as eluting solvents to give the title compound. LC/MS: (M+l) : 487.17.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Chloro-6-iodo-2-(methylsulfonyl)-1H-benzo[d]imidazole, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MANDAL, Mihir; TANG, Haifeng; XIAO, Li; SU, Jing; LI, Guoqing; YANG, Shu-Wei; PAN, Weidong; TANG, Haiqun; DEJESUS, Reynalda; HICKS, Jacqueline; LOMBARDO, Matthew; CHU, Hong; HAGMANN, William; PASTERNAK, Alex; GU, Xin; JIANG, Jinlong; DONG, Shuzhi; DING, Fa-Xiang; LONDON, Clare; BISWAS, Dipshikha; YOUNG, Katherine; HUNTER, David, N.; ZHAO, Zhiqiang; YANG, Dexi; WO2015/112441; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 1450-93-7, name is 1H-imidazol-2-amine sulfate(2:1), 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 1450-93-7, name: 1H-imidazol-2-amine sulfate(2:1)

EXAMPLE 13 7-Methyl-5-[3-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine A mixture of 5.14 g of (3-dimethylamino)-1[3-(trifluoromethyl)phenyl]-2-butene-1-one, 1.64 g of anhydrous sodium acetate and 2.64 g of 2-aminoimidazole hemisulfate in 100 ml of glacial acetic acid was refluxed for six hours. The solvent was removed in vacuo and the solid residue was partitioned between a saturated aqueous sodium bicarbonate solution and dichloromethane. The organic layer was separated and dried over powdered anhydrous sodium sulfate, then passed through a short column of a hydrous magnesium silicate. The effluent was refluxed on a steam bath with the gradual addition of hexane until crystallization was noted. On cooling the product was separated and collected by filtration and gave 2.55 g of the desired compound as off-white crystals, m.p. 170-172 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-imidazol-2-amine sulfate(2:1), and friends who are interested can also refer to it.

Reference:
Patent; American Cyanamid Company; US5037980; (1991); A;,
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. 15813-09-9, name is 4,5-Diiodo-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Formula: C3H2I2N2

A mixture of 2 (12.0 g, 37.5 mmol)and Na2SO3 (23.6 g, 187.3 mmol) in EtOH (120 mL) and H2O (20 mL)was refluxed for 72 h. The mixture was concentrated in vacuo andthe residue was extracted with ethyl acetate. The crude productwas purified by recrystallization from dichloromethane to afford 3as a white solid (3.5 g, 48.1%). Mp 137e139 C. 1H NMR (300 MHz,Chloroform-d) d(ppm) 7.0 (s, 1H), 7.5 (s, 1H). MS (EI) m/z 194.9[MH].

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 15813-09-9.

Reference:
Article; Zou, Yi; Wang, Fang; Wang, Yan; Sun, Qirui; Hu, Yue; Li, Yuezhen; Liu, Wen; Guo, Wenjie; Huang, Zhangjian; Zhang, Yihua; Xu, Qiang; Lai, Yisheng; European Journal of Medicinal Chemistry; vol. 140; (2017); p. 293 – 304;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 41716-18-1, These common heterocyclic compound, 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, 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.

To a solution of intermediate 30-d (2.0 g, 3.73 mmol) in DMF, cooled to 0¡ã C., were sequentially added 1-methyl-1H-imidazole-4-carboxylic acid (564 mg, 4.47 mmol), HATU (1.70 g, 4.47 mmol) and DIPEA (2.60 mL, 14.91 mmol) and the reaction mixture was stirred at 0¡ã C. for 2 hours. Saturated aqueous ammonium chloride and ethyl acetate were added; the organic layer was separated, washed with saturated aqueous ammonium chloride, saturated aqueous NaHCO3 and brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification by silica gel chromatography provided intermediate 31-a as a white foam

Statistics shows that 1-Methyl-1H-imidazole-4-carboxylic acid is playing an increasingly important role. we look forward to future research findings about 41716-18-1.

Reference:
Patent; Pharmascience Inc.; Laurent, Alain; Proulx, Melanie; Rose, Yannick; Denissova, Irina; Dairi, Kenza; Jarvis, Scott; Jaquith, James B.; (189 pag.)US9284350; (2016); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 111851-98-0, These common heterocyclic compound, 111851-98-0, name is 1-Ethyl-1H-imidazole-2-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.

[00453] (¡ê)-3-(l-ethyl-lH-imidazol-2-yl)-l-(thiazol-2-yl)prop-2-en-l-one was prepared from l-(4-methylthiazol-2-yl)-2-(triphenyl- 5-phosphanylidene)ethan-l-one (1.0 equiv.) and 1 -ethyl- lH-imidazole-2-carbaldehyde5 via Wittig reaction (24 h) in 56 % isolated yield, using synthetic procedures described for the preparation of the analog SW209415. H NMR (400 MHz, CDCI3) delta 8.26 (d, / = 15.4 Hz, 1H), 8.03 (d, / = 3.0 Hz, 1H), 7.82 (d, / = 15.4 Hz, 1H), 7.67 (d, 7 = 3.0 Hz, 1H), 7.22 (s, 1H), 7.07 (d, 7 = 1.2 Hz, 1H), 4.15 (q, 7 = 7.4 Hz, 2H), 1.45 t, / = 7.3 Hz, 3H). ESI-MS (m/z): 234.1 [M+H]+.

Statistics shows that 1-Ethyl-1H-imidazole-2-carbaldehyde is playing an increasingly important role. we look forward to future research findings about 111851-98-0.

Reference:
Patent; CASE WESTERN RESERVE UNIVERSITY; BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM; MARKOWITZ, Sanford D.; READY, Joseph; ZHANG, Yongyou; ANTCZAK, Monika; WILLSON, James K.V.; POSNER, Bruce A.; GREENLEE, William; (254 pag.)WO2016/168472; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 23328-88-3, 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. 23328-88-3 name is 2-Bromo-4-methyl-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.

2-bromo-1-(5-fluoro-3-methoxy-2-nitrophenyl)-4-methyl-1H-imidazole (B) A mixture of 1,5-difluoro-3-methoxy-2-nitrobenzene (9 g, 47.6 mmol), 2-bromo-4-methylimidazole (7.7 g, 47.6 mmol) and potassium carbonate (14.5 g, 104.7 mmol) in 240 mL DMF was stirred at room temperature overnight. The majority of solvent was removed by rotavap and the residue was diluted with ethyl acetate and washed with water. The aqueous phase was extracted with ethyl acetate and the combined organic phase was washed with water, brined, dried over magnesium sulfate. Condensation and purification using 5-10% ethyl acetate in dichloromethane as eluent provided 4.8 g (31% yield) of 2-bromo-1-(5-fluoro-3-methoxy-2-nitrophenyl)-4-methyl-1H-imidazole as a yellow solid. 1H NMR (400 MHz, DMSO) delta ppm 7.60 (dd, 1H), 7.38 (dd, 1H), 7.21 (s, 1H), 3.98 (s, 3H), 2.09 (s, 3H). EIMS 330.0 [M+H]+.

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

Reference:
Patent; ELBION GMBH; WYETH; US2009/143367; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 14741-71-0, name is Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate, 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 14741-71-0, category: imidazoles-derivatives

General procedure: To a solution of compound 3 (2.04 g, 0.01 mol) in ethanol (30 mL) containing piperidine (0.50 mL) either benzaldehyde (1.06 g, 0.01 mol) or 4-methoxy benzaldehyde (1.31 g, 0.01 mol) or 4-chlorobenzaldehyde (1.34 g, 0.01 mol) was added. The reaction mixture, in each case, was heated under reflux for 3 h then poured onto ice/water mixture containing few drops of hydrochloric acid and the formed solid product was collected by filtration. Ethyl 2-(1H-benzo[d]imidazol-2-yl)-3-phenylacrylate (7a). Gray crystals from ethanol; yield:2.45 g (77%); m.p. > 300 oC. IR, : 3478-3329 (NH), 3057 (CH aromatic), 2962, 2873 (CH3,CH2), 1688 (C=O), 1646 (C=N), 1630 (C=C). 1H-NMR: : 1.14 (t, 3H, J = 7.66 Hz, CH3), 4.21(q, 2H, J = 7.66 Hz, CH2), 6.24 (s, 1H, CH=C), 7.29-7.38 (m, 9H, C6H5, C6H4), 8.26 (s, 1H, NH,D2O exchangeable). 13C NMR (DMSO): 16.3 (ester CH3), 52.5 (ester CH2), 89.3, 90.2 (CH=C),120.6, 122.1, 123.2, 123.9, 124.1, 124.6, 125.8, 126.2, 127.8, 128.2, (C6H5, C6H4), 164.8 (CO),172.6 (C=N); Anal. calcd for C18H16N2O2: C, 73.95; H, 5.52; N, 9.58%. Found: C, 72.73; H,5.49; N, 9.37%. MS: m/z: (%) 292 (M+, 64%).

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

Reference:
Article; Mohareb, Rafat M.; Gamaan, Marwa S.; Bulletin of the Chemical Society of Ethiopia; vol. 32; 3; (2018); p. 541 – 557;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 124750-92-1, 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 124750-92-1 as follows.

Step 3:; A solution of dicyclohexylcarbodiimide (DCC) (267.4 mg; 1.3 eq.) in anhydrous THF (10 ml) was added dropwise to a stirred solution of losartan acid (472 mg; 1.08 mmol) prepared as described in step 2, 5-(4-hydroxyphenyl)-3H-1,2-dithiol-3-thione (244.5 mg; 1.08 mmol) prepared as above described (step 1) and dimethylaminopyridine (DMAP, 7 mg) in 15 ml of tetrahydrofurane (THF). The reaction is performed at room temperature, stirring under nitrogen for 5 hours. At the end of the reaction the dicyclohexylurea (DCC) is removed by filtration. The solution is evaporated to dryness and the crude product was purified by column chromatography (on silica gel) eluting with CH2C12-methanol (97:3) to give an orange solid with melting point 180-185 C.

According to the analysis of related databases, 124750-92-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CTG Pharma S.r.l.; EP1980559; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem