Tag: M.W=200-300

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. 2963-77-1, name is 4-(1H-Benzo[d]imidazol-2-yl)aniline, A new synthetic method of this compound is introduced below., Quality Control of 4-(1H-Benzo[d]imidazol-2-yl)aniline

General procedure: The mixture of 0.1mol of phenoxy acetic acid derivative(PAA1-PAA5) and 0.1mol of dicyclohexyl carbodiimide in10 mL dichloromethane was stirred at room temperature.After 30 minutes, a solution of AB or APB in 20 ml of dichloromethaneand 5 ml of pyridine was added. The reactionmixture was stirred initially at 0C for 2 h followed by stirring at room temperature for 12 h. The precipitated dicyclohexylureawas removed by filtration and the solvent wasdistilled at reduced pressure on rotary vacuum evaporator.The dried product was dissolved in ethyl acetate (10 mL) andthe solution was washed with 10% aqueous solution of sodiumbicarbonate followed by distilled water to remove thetraces of residual dicyclohexylurea. The ethyl acetate layerwas dried with anhydrous magnesium sulphate and then solventwas distilled off to obtain the crude product which wasrecrystallized from ethanol-water mixture.

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; Singh, Gurmeet; Bansal, Yogita; Bansal, Gulshan; Goel, Rajesh Kumar; Medicinal Chemistry; vol. 10; 4; (2014); p. 418 – 425;,
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Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 86718-07-2, name is Ethyl 4-(1-Imidazolyl)benzoate, 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 86718-07-2, HPLC of Formula: C12H12N2O2

Alternatively the 4-(1-imidazolyl)-benzylalcohol can be obtained by reduction of the ethyl 4-(1-imidazolyl)-benzoate with LiAlH4. The 4-(1-imidazolyl)-benzylalcohol thus obtained is solved in diethyl ether and transformed into the corresponding hydrochloride by bubbling gaseous HCl.

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; Farmitalia Carlo Erba S.R.L.; US5238953; (1993); 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. 28890-99-5, name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole

c) 1.00 g (2.68 mmol) 6-bromo-2-iodo-dibenzofuran, 1.75 g (5.36 mmol) caesium carbonate, 130 mg (0.67 mmol) copper(l) iodide and 150 mg (1.34 mmol) L-proline are added to 670 mg (3.22 mmol) 5H-benzimidazo[1 ,2-a]benzimidazole in 20 ml DMSO under nitrogen. The reaction mixture is stirred for 18 h at 100 C and filtered. THF and toluene are added to the organic phase and the organic phase is washed with water. The organic phase is dried with magnesium sulfate and the solvent is distilled off. The product can be used without further purification in step d) (yield = 650 mg (78 %)).1H NMR (400 MHz, CDCI3): delta 8.66 (d, J = 2.2 Hz, 1 H), 8.13-8.19 (m, 2H), 7.96-8.07 (m, 3H), 7.66-7.78 (m, 3H), 7.25-7.45 (m, 5H).

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 28890-99-5.

Reference:
Patent; BASF SE; SCHAeFER, Thomas; FIGUEIRA DUARTE, Teresa, Marina; SCHILDKNECHT, Christian; LANGER, Nicolle; HEINEMEYER, Ute; WOLLEB, Heinz; WATANABE, Soichi; LENNARTZ, Christian; WAGENBLAST, Gerhard; WOLLEB, Annemarie; BARDON, Kristina; BENEDITO, Flavio, Luiz; WO2012/130709; (2012); A1;,
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Imidazole | C3H4N2 – PubChem

Electric Literature of 2963-77-1, 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. 2963-77-1 name is 4-(1H-Benzo[d]imidazol-2-yl)aniline, 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 stannous chloride 1.6 g, (8.4 mmol) in 30 mL water was added 1.75g (8.4 mmol) of PBA in 30mL ethanol. The reaction mixture was stirred at room temperature for 30 min and then a solution of BPE (2 g, 8.4 mmol in 30 mL water) was added to mixture and heated at 100C for 14 h. The progress of reaction was controlled with TLC (DMF/water: 50/50). At the end of reaction, the reaction mixture was cooled, diluted with ethanol (40 mL), filtered and washed with ethanol and then with DMF to obtain a red precipitate. Yield: 85%, m.p. : 230C; m.f.: C28H26N6SnCl2. UV-vis (DMSO); max (nm): 280, 310, 430. IR (KBr, max, cm-1): 3443 (m), 3338 (m), 3224(m), 1601 (s), 1567 (s), 1497 (s), 1411 (m), 1320 (s), 1236 (s), 1168 (s), 1110 (s), 1069 (s), 849 (s), 744 (m), 607 (m) 498 (m), 434 (m).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(1H-Benzo[d]imidazol-2-yl)aniline, and friends who are interested can also refer to it.

Reference:
Article; Aroua, Lotfi M.; Asian Journal of Chemistry; vol. 32; 6; (2020); p. 1266 – 1272;,
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. 4499-07-4, name is 2-(1H-Benzo[d]imidazol-2-yl)ethanamine dihydrochloride, A new synthetic method of this compound is introduced below., Recommanded Product: 4499-07-4

To a solution of benzimidazole ethylene amine dihydrochloride (100 mg, 0.43 mmol), 3,4-dimethylphenoxyacetic acid (77 mg, 0.43 mmol), and BOP reagent (190 mg, 0.43 mmol) in acetonitrile (5 mL) was added triethylamine (0.23 mL, 1.72 mmol). After stirring at room temperature overnight, the solvent was removed under vacuum. The residue was taken up with water and saturated sodium bicarbonate (20 mL), extracted with dichloromethane (30 mL x 2), dried and removed the solvent. The crude mixture was purified by using Gilson HPLC to give white solid 5 as a TFA salt (170 mg) at 93 % yield. MUX LC/MS (10-99%) M+1/Z 324.163 retention time 2.62 min ; 1H NMR (DMSO) 8 2.12 (s, 3H), 8 2.15 (s, 3H), 8 2.99 (t, 2H, J = 5.88 Hz), 8 3.59 (m, 2H), 8 4.40 (s, 2H), 8 6.64 (dd, 1H, J = 2 Hz, 6.5 Hz), 8 6.75 (d, 1H, J = 1.8 Hz), 8 6.98 (8, 1H, J = 6.6 Hz), 8 7.12 (m, 2H), 7.40 (d, 1H, J = 5.76 Hz), 7.53 (m, 1H), 8.30 (t, 1H, J = 4.56 Hz), 12.24 (s, 1H) ; 13C NMR (DMSO) 8 18.4, 8 19. 57, 8 28.58, 8 36.74, 8 67.07, 8 110.8, 8 111.58, 8 116.13, 8 118.12, 8 120.86, 8 121.52, 8 128. 70, 8 130.12, 8 134.21, 8 137.25, 8 143. 24, 8 152. 74, 8 155.73, 8 167. 85.

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; VERTEX PHARMACEUTICALS, INCORPORATED; WO2005/42497; (2005); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 95470-42-1, A common heterocyclic compound, 95470-42-1, name is Ethyl 2-bromo-4-methyl-1H-imidazole-5-carboxylate, molecular formula is C7H9BrN2O2, 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.

(2) Ethyl 2-bromo-4-methyl-1H-imidazole-5-carboxylate (2.75 g, 11.81 mmol) described in (1) was dissolved in DMF (20 mL), potassium carbonate (3.26 g, 23.62 mmol) and 2,5-dichlorobenzyl bromide (3.4 g, 14.17 mmol) were added thereto, and the mixture was stirred at 90° C. for 3 hours. After the reaction, water was added and the mixture was extracted twice with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and subsequently dried over sodium sulfate. After concentrating the organic layer, the residue was purified by column chromatography to obtain ethyl 2-bromo-1-(2,5-dichlorobenzyl)-4-methyl-1H-imidazole-5-carboxylate (1.72 g): 1H-NMR (CDCl3) delta: 7.34 (1H, d, J=8.8 Hz), 7.20 (1H, dd, J=8.8, 2.4 Hz), 6.40 (1H, d, J=2.4 Hz), 5.60 (2H, s), 4.25 (2H, q, J=7.2 Hz), 2.56 (3H, s), 1.27 (3H, t, J=7.1 Hz).

The synthetic route of 95470-42-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TEIJIN PHARMA LIMITED; MIYAMOTO, Hidetoshi; NOZATO, Hisae; MARUYAMA, Akinobu; (16 pag.)US2017/144987; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 152628-03-0,Some common heterocyclic compound, 152628-03-0, name is 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid, molecular formula is C12H14N2O2, 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 2; Variant 2; Methanesulphonic acid is heated to about 80 C. At a temperature of 75 C. to 85 C., 2-propyl-4-methyl-1H-benzimidazole-6-carboxylic acid is added. Then at 85 C. to 95 C. N-methyl-o-phenylene-diamine is added.The mixture is heated to110 C. to 130 C. and phosphorus pentoxide is metered in until an internal temperature of not more than 160 C. is reached. Then the mixture is stirred for 3 hours at a maximum temperature of 145 C. It is cooled to <100 C. and water is metered into the reaction mixture. 50% sodium hydroxide solution is added at <100 C. until a pH of less than 3 is obtained.Finally, treatments with charcoal are carried out at <100 C.At a temperature of <80 C. isopropanol is added and the mixture is adjusted with sodium hydroxide solution to a pH between 4.5 and 7. The aqueous phase is separated off. In order to precipitate dimethyl-2'-propyl-2,5'-bi-1H-benzimidazole water is metered in, the contents of the apparatus are cooled to at least 40 C. for technical reasons and the product is isolated.Yield: 78-90% of theoryHPLC purity: >99.5%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid, its application will become more common.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2011/190508; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 95470-42-1, 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. 95470-42-1, name is Ethyl 2-bromo-4-methyl-1H-imidazole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

(1) Ethyl 2-bromo-4-methyl-1 H-imidazole-5-carboxylate (2.75 g, 11.81 mmol) described in Example 1(1) was dissolved in DMF (20 mE), potassium carbonate (3.26 g, 23.62 mmol) and 2,5-dichlorobenzyl bromide (3.4 g, 14.17 mmol) were added thereto, and the mixture was stirred at 90° C. for 3 hours. Afier the reaction, water (50 mE) was added and the mixture was extracted twice with ethyl acetate (50 mE). The organic layer was washed with saturated aqueous sodium chloride and subsequently dried over sodium sulfate. After concentrating the organic layer, the residue was purified by column chromatography to obtain ethyl 2-bromo-1 -(2,5- dichlorobenzyl)-4 -methyl-i H-imidazole-5-carboxylate(1.72 g):10160] ?H-NMR (CDC13) oe: 7.34 (1H, d, J=8.8 Hz), 7.20(1H, dd, J=8.8, 2.4 Hz), 6.40 (1H, d, J=2.4 Hz), 5.60 (2H, s),4.25 (2H, q, J=7.2 Hz), 2.56 (3H, s), 1.27 (3H, t, J=7.1 Hz);10161] ESI-MS mlz=391 (M+H).

The chemical industry reduces the impact on the environment during synthesis Ethyl 2-bromo-4-methyl-1H-imidazole-5-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Teijin Pharma Limited; Maruyama, Akinobu; Kamada, Hirofumi; Fujinuma, Mika; Takeuchi, Susumu; Saitoh, Hiroshi; Takahashi, Yoshimasa; US2015/284358; (2015); 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. 39513-26-3, name is 5-Bromo-1,3-dihydrobenzoimidazol-2-one, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H5BrN2O

5-Bromo-1,3-dihydrobenzimidazol-2-one (1.30 g, 6.10 mmol), 1-tert-butoxycarbonyl-2,5-dihydro-1H-pyrrole-3-boronic acid pinacol Ester (1.77 g, 6.00 mmol), 1,1′-bisdiphenylphosphinoferrocene palladium dichloride (230 mg,0.314 mmol) and potassium carbonate (2.49 g, 18.0 mmol) were mixed in N,N-dimethylformamide (30 mL).The oxygen was replaced by nitrogen, and then heated to 100 C for 16 hours.The reaction system was diluted with ethyl acetate (300 mL), and the organic phase was washed with water (100 mL×2).The mixture was washed with saturated brine (100 mL × 5) and dried over anhydrous sodium sulfate.The desiccant was removed by filtration, and the solvent was concentrated under reduced pressure.Column chromatography purification (petroleum ether / ethyl acetate / ethanol = 12 / 3 / 1, 3 / 3 / 1),A pale yellow solid (300 mg, yield 17%) was obtained.

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 39513-26-3.

Reference:
Patent; Maidikang (Shanghai) Bio-pharmaceutical Technology Co., Ltd.; Dang Zhu; Ke Lisiting·juecai; Luo Zhen; Wang Liugang; Bao Dan; Qi Tafamingrenqingqiubugongkaixingming; (106 pag.)CN109956931; (2019); A;,
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 53484-16-5 as follows. HPLC of Formula: C8H7BrN2

A mixture containing 6-bromo-1 -methyl-benzimidazole (2.38 mmol), 4-amino-3-fluoro-benzonitrile (3.57 mmol),XPhos (0.95 mmol), Cs2CO3 (7.14 mmol) and Pd(OAc)2 (0.71 mmol) in dry toluene (8 mE) was stirred at 1100 C. forapproximately 16 h. The mixture was diluted (EtOAc), washed (H20), dried (Na2SO4) and concentrated to yield thedesired product 3-fluoro-4-[(3-methylbenzimidazol-5-yl)amino]benzonitrile.

According to the analysis of related databases, 53484-16-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GALAPAGOS NV; Menet, Christel Jeanne Marie; Mammoliti, Oscar; Blanc, Javier; Orsulic, Mislav; Roscic, Maja; (81 pag.)US9440929; (2016); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem