Imidazoles-derivatives

These common heterocyclic compound, 29914-81-6, name is 1,3-Bis(1H-benzo[d]imidazol-2-yl)benzene, 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. SDS of cas: 29914-81-6

1,3-bis(1H-benzo[d]imidazol-2-yl)benzene (MBImB) was first synthesized according to our earlier report [19]. 10.01 g MBImB was dissolved in anhydrous DMF, and then 3.5 g NaH encapsulated in mineraloil (60%) was added and stirred for 0.5 h. When the NaH reaction was completed, 1-bromopropane (9.0 g) was added. After degassing, the solution was heated at 100 C overnight under nitrogen atmosphere.After cooling, 200 ml water was added, and the aqueous layer was washed with CH2Cl2 (2¡Á30 ml). The combined organic extract was dried over Na2SO4, filtered, and concentrated under high vacuum. The pure product was obtained as a red viscous liquid. Yield, 71%. 1H NMR(300 MHz, CDCl3) delta 8.02 (s, 1 H), 7.90-7.78 (m, 4 H), 7.72-7.65 (m,1 H), 7.44 (dd, J=9.1, 5.1 Hz, 2 H), 7.39-7.29 (m, 4 H), 4.30-4.20(m, 4 H), 1.91-1.77 (m, 4 H), 0.85 (t, J =7.4 Hz, 6 H). ESI-MS m/z:394.1.

The synthetic route of 1,3-Bis(1H-benzo[d]imidazol-2-yl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Chao-Jie; Yin, Shao-Yun; Wang, Hai-Ping; Wei, Zhang-Wen; Pan, Mei; Journal of Photochemistry and Photobiology A: Chemistry; vol. 379; (2019); p. 99 – 104;,
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1072-62-4, name is 2-Ethyl-1H-imidazole, 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. Quality Control of 2-Ethyl-1H-imidazole

To a stirred slurry of9.95 g (0.125 mole) copper oxide in 100 mL 2% aqueous acetic acid at 95 0C was added 25.24 g (0.263 mole) 2-ethylimidazole. The mixture was brought to a boil and maintained under reflux for several hours. The resulting slurry was filtered and the solids washed with water and dried at 105 0C to give a brown powder. The product (23.92 g, 75% yield) gave a unique X-ray diffraction pattern and was confirmed to have the composition of copper 2- ethylimidazolate, by elemental analysis. Some unreacted copper oxide was present in the product.

The synthetic route of 1072-62-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; U.S. BORAX INC.; WO2007/87434; (2007); A2;,
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Some common heterocyclic compound, 5465-29-2, name is 2-Propylbenzimidazole, molecular formula is C10H12N2, 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. category: imidazoles-derivatives

Step 4) Methyl 2-[4-[(2-Propyl-1H-benzimidazol-1-yl)methyl]phenyl]-1-cyclopentene-1-carboxylate To a cooled (0 C.), stirred partial solution of 2-propyl-1H-benzimidazole (0.79 g, 4.96 mmol) in DMF (4 mL) was added NaH (60% dispersion in mineral oil; 0.20 g, 4.96 mmol). After 1.5 h, a solution of methyl [2-[(4-chloromethyl)phenyl]-1-cyclopentene]-1-carboxylate (1.13 g, 4.51 mmol) in DMF (1.5 mL) was added and the resultant mixture was stirred at room temperature for 18 h. Water was added and the mixture was extracted with EtOAc. The combined extracts were washed with brine, dried, and concentrated. Purification by flash chromatography (30% EtOAc/hexane) gave 1.63 g (96%) of product as a yellow oil. 1 H NMR (CDCl3) delta 1.00 (t, J=7.5 Hz, 3H), 1.86 (m, 2H), 1.95 (m, 2H), 2.79 (m, 6H), 3.59 (s, 3H), 5.33 (s, 2H), 6.99 (d, J=8.2 Hz, 2H), 7.28 (m, 5H), 7.77 (d, J=7.5 Hz, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5465-29-2, its application will become more common.

Reference:
Patent; American Home Products Corporation; US5283242; (1994); A;,
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Synthetic Route of 144690-33-5, The chemical industry reduces the impact on the environment during synthesis 144690-33-5, name is Ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2′-(1-trityl-1H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate, I believe this compound will play a more active role in future production and life.

To a 10 L reaction flask was added 257 gPhenyl) methylimidazol-1-yl) phenyl] propan-1- {4- [2- (triphenylmethyl- Carboxylic acid ethyl ester (Compound II) and 2.8 L 1,4-dioxane were added and dissolved by mechanical stirring,Heating to 45 C, adding 28.6g of sodium hydroxide solution, the reaction 4.5h. To the reaction mixture, 1.5 L of ethyl acetate was added,Stirring, standing layered, separate the organic phase. The aqueous phase was extracted with 1 L of ethyl acetate. The organic phases were combined and the organic phase was chlorinated with 4.5 LSodium aqueous solution. The organic phase was cooled in an ice bath and adjusted to pH 3 to 5 with 20% aqueous acetic acid. The filter cake was washed with 5 L of ethyl acetateEster. The filter cake was dried in a dry oven to constant weight to give 198.6 g of product as a white solid. The yield was 80.4% by weight.The product was 98.5% by HPLC.

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 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2′-(1-trityl-1H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bengbu Tu Shan Fengyuan Pharmaceutical Co., Ltd.; Ma, Qisheng; Li, Baoqin; Sun, Peng; (18 pag.)CN105418593; (2016); A;,
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Electric Literature of 6160-65-2,Some common heterocyclic compound, 6160-65-2, name is 1,1′-Thiocarbonyldiimidazole, molecular formula is C7H6N4S, 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: To a stirring solution of 1,1?-thiocarbonyldiimidazole (1.2 equiv) in5 mL of DMF at 50 C was added a solution of TEA (1 equiv) and amine5 (1 equiv) in DMF dropwise. The resulting solution stirred at roomtemperature for 1-24 h and was monitored by TLC. The resulting crudesolution of the isothiocyanate was used in the next step without purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,1′-Thiocarbonyldiimidazole, its application will become more common.

Reference:
Article; Chapa, Jorge De La; Valdez, Matthew; Ruiz, Franscisco; Gonzales, Keith; Mitchell, Wes; McHardy, Stanton F.; Hart, Matthew; Polusani, Srikanth R.; Gonzales, Cara B.; Bioorganic and Medicinal Chemistry; vol. 27; 1; (2019); p. 208 – 215;,
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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. 1402838-08-7, name is 2-(1-Trityl-4-imidazolyl)benzaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C29H22N2O

Dimethyl (2-(quinoxalin-2-yl)-2-oxoethyl)phosphate (0803-134) (224 mg, 0.80 mmol, 1.1 eq),2-(1-trityl-1H-imidazol-4-yl)benzaldehyde (0105-1) (300 mg, 0.73 mmol, 1.0 equiv) andCesium carbonate (472 mg, 1.45 mmol, 2.0 eq.)Added to 40 ml of isopropanol,The reaction was stirred at room temperature overnight, concentrated under reduced pressure, ethyl acetate and water were added, and the mixture was separated and dried over anhydrous sodium sulfate.Shrink to give yellow solid product 1-(quinoxalin-2-yl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)propan-2-ene-1- Ketone (400 mg, crude product)

The synthetic route of 1402838-08-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangzhou Bi Beite Pharmaceutical Co., Ltd.; Cai Xiong; Qian Changgeng; Weng Yunwo; Qing Yuanhui; Liu Bin; Lin Mingsheng; Wang Yanyan; (126 pag.)CN107383024; (2017); A;,
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Electric Literature of 53484-16-5, 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. 53484-16-5, name is 6-Bromo-1-methyl-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of Pd2(dba)3 (0.01 mmol) and Xantphos (0.01 mmol) in 1,4-dioxane (1 mL) was sonicated and added under nitrogen to a mixture of 6-bromo-1-methyl-benzimidazole (0.45 mmol), 2,3-dihydro-1,4-benzodioxin-6-amine (0.58 mmol) and Cs2CO3 (0.62 mmol) in 1,4-dioxane (2 mL). The mixture was stirred at 110¡ã C. for 12 h. The mixture was diluted (DCM), washed (H2O), dried (phase separator and concentrated. The residue was purified by prep HPLC to yield the desired product (Compound B). [0542] MW: 281.3. MS Ms?d: 282.1. [0543] NMR: 1H NMR (400 MHz, DMSO-d6): delta=7.94 (1H, s), 7.80 (1H, br s), 7.45 (1H, d), 7.05 (1H, d), 6.86 (1H, dd), 6.73 (1H, dd), 6.61-6.57 (2H, m), 4.22-4.16 (4H, m), 3.71 (3H, s).

The chemical industry reduces the impact on the environment during synthesis 6-Bromo-1-methyl-1H-benzo[d]imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MENET, Christel Jeanne Marie; MAMMOLITI, Oscar; BLANC, Javier; ORSULIC, Mislav; ROSCIC, Maja; US2015/203455; (2015); A1;,
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Reference of 1402838-08-7, These common heterocyclic compound, 1402838-08-7, name is 2-(1-Trityl-4-imidazolyl)benzaldehyde, 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-(1-Trityl-1H-imidazol-4-yl)benzaldehyde (4.0 g, 9.66 mmol) was dissolved in dry THF (20 mL)In a mixed solution with anhydrous EtOH (20 mL), cooled to 0 C, then EtONa (986 mg, 14.5 mmol), tert-butyl 4-acetylpiperidine-1-carboxylate (2.29 g, 10.1 mmol).Then the reaction solution was stirred at room temperature overnight, and the reaction was complete by LCMS.After that, it was diluted with ice water (30 mL), and the THF was evaporated under reduced pressure, and filtered, and the filter cake was drained as much as possible to obtain a crude white solid.(E)-4-(3-(2-(1-tritylmethyl-1H-imidazol-4-yl)phenyl)acryloyl)piperidine-1-carboxylic acid tert-butyl ester(6.0g), used directly in the next step.

The synthetic route of 1402838-08-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shenzhen Weixin Biological Technology Co., Ltd.; Yu Jindi; Lu Xianping; Li Zhibin; Xin Lijun; Zhu Jiangfei; Fu Chao; (67 pag.)CN108203438; (2018); A;,
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Synthetic Route of 6775-40-2, 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. 6775-40-2, name is 5-Phenyl-1H-imidazol-2-amine, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a stirred solution ofaldehyde (1 mmol), amine (1 mmol), CCl3CN (2 mmol) in PEG-400 (5mL) at 0 oC, a solution of H2O2 (30%) (3mmol)was added drop wise. Then the reaction mixture was stirred at room temperature for 8-12 h. After completion ofthe reaction (monitored by TLC), the reaction mixture was poured into ice water (50 mL). The solid obtained wasfiltered, washed with water and crude product was purified by column chromatography (silica gel, 60-120 mesh)using hexane/ethylacetate (6:4) as eluent.

The chemical industry reduces the impact on the environment during synthesis 5-Phenyl-1H-imidazol-2-amine. I believe this compound will play a more active role in future production and life.

Reference:
Article; Gaddam, Lakshmi Teja; Thata, Sreenivasulu; Adivireddy, Padmaja; Venkatapuram, Padmavathi; Arkivoc; vol. 2019; 6; (2019);,
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Reference of 28890-99-5, These common heterocyclic compound, 28890-99-5, name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, 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 1 a) 20 g (96.5 mmol) 6H-benzimidazolo[1 ,2-a]benzimidazole is dissolved in 400 ml trifluoro- acetic acid under nitrogen. 43.4 g (193 mmol) N-lodosuccinimide is added in 10 minutes. The reaction mixture is stirred at 25 C for 24 h under nitrogen. The precipitated product is filtered off and crystalized from trifluoroacetic acid (yield: 19.2 g (43 %)). 1 H NMR (400 MHz, TFA-d1): delta 8.77-8-78 (m, 2H), 8.34-8.37 (m, 2H), 7.91-7.94 (m, 1 H).

The synthetic route of 28890-99-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IDEMITSU KOSAN CO., LTD (IKC); SCHAeFER, Thomas; RAIMANN, Thomas; NAGASHIMA, Hideaki; (108 pag.)WO2016/16791; (2016); A1;,
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