Month: December 2020

These common heterocyclic compound, 583-42-6, name is 5-Fluoro-1H-benzo[d]imidazole-2(3H)-thione, 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. Computed Properties of C7H5FN2S

Step 2) Synthesis of 2-chloro-5-fluoro-1H-benzo [d] imidazole To a 50 mL of reaction flask were added 5-fluoro-1H-benzo [d] imidazole-2-thiol (1.00 g, 6.57 mmol) and phosphorus oxychloride (25 mL) . The mixture was refluxed for 13 h. After the reaction is complete, the mixture was concentrated to remove excess phosphorus oxychloride. The resulting mixture was quenched with saturated sodium bicarbonate solution (15 mL) , and extracted with ethyl acetate (10 mL ? 3) . The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound as a pale yellow solid (1.03 g, 92.0%) .MS (ESI, pos. ion) m/z: 171.05 [M+H] +.

The synthetic route of 5-Fluoro-1H-benzo[d]imidazole-2(3H)-thione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; JIN, Chuanfei; ZHANG, Ji; (90 pag.)WO2017/88759; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 939-70-8, 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 939-70-8 as follows.

General procedure: A solution of 2-acetyl-benzimidazole 4(3.2 g, 20 mmol) and the diversely substituted aromatic aldehydes5a-h (24 mmol) in 40 ml of absolute methanol were taken in a flask.Potassium hydroxide (8.0 g, 142.6 mmol) was added and the reactionmixture was stirred for 24 h at room temperature under TLCmonitoring. The mixture was then poured into crushed ice water.The product obtained is filtered and washed with distilled waterand finally recrystallized from methanol.

According to the analysis of related databases, 939-70-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Djemoui, Amar; Naouri, Abdelkader; Ouahrani, Mohammed Ridha; Djemoui, Djamila; Lahcene, Souli; Lahrech, Mokhtar Boualem; Boukenna, Leila; Albuquerque, Helio M.T.; Saher, Liza; Rocha, Djenisa H.A.; Monteiro, Fatima Liliana; Helguero, Luisa A.; Bachari, Khaldoun; Talhi, Oualid; Silva, Artur M.S.; Journal of Molecular Structure; vol. 1204; (2020);,
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Imidazole | C3H4N2 – PubChem

Related Products of 144690-33-5,Some common heterocyclic compound, 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, molecular formula is C45H44N6O3, 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.

123.2g of compound and 2.5g of potassium hydroxide solid were added to a 500ml four-necked flask.DMAC76g, heated to 50 C, stirred for about 6h,The TLC dot plate showed that the compound 1 point disappeared, that is, the end of the hydrolysis reaction was judged.Cool to 15 ¡À 5 C, add KBr 0.64g, add DMDO-C16.5g, DMAC 10g,After about 40 minutes, the temperature was raised to 25¡À5C for 2h, then the temperature was raised to 50C, the reaction was about 6h, and the temperature was lowered again to 20¡À5C for 5h. The reaction solution was added with 324g water and 208g of dichloromethane.Shake well and let the layers separate. The aqueous layer was extracted with 70 g of dichloromethane and combined with several layers.It was washed twice with 206 g of water, and the last aqueous layer was extracted with 100 g of dichloromethane.The organic layers were combined and dried under reduced pressure at 45 C.After adding 100g of the upper batch of crystallization, the mother liquid is heated and refluxed for 25¡À5 minutes, and then naturally cooled.Then crystallization at 0 C for 6 h,Drying by suction filtration to obtain 23.2 g of trityl olmesartan medoxomil white solid powder.The yield was 93.4%. HPLC analysis, purity 99.7%, acid miscellaneous <0.05%,The olefinic impurity is <0.1%, and the other unknown single impurities are <0.1%. The synthetic route of 144690-33-5 has been constantly updated, and we look forward to future research findings. Reference:
Patent; Zhejiang Huahai Pharmaceutical Co., Ltd.; Xiong Xueqiang; Li Guoxiang; Wang Jiquan; (6 pag.)CN103880825; (2019); B;,
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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. 71759-87-0, name is 4-Iodo-1-methyl-1H-imidazole, A new synthetic method of this compound is introduced below., Computed Properties of C4H5IN2

To a solution of 2-benzyloxy-5-(4,4, 5,5-tetramethyl-[i , 3,2]dioxaborolan-2-yl)benzamide (Preparation 162, 5 g, i4.i6 mmol) and 4-iodo-i-methyl-iH-imidazole (2.94 g, i4.i6 mmol) in DMF (60 mL) was added a solution of potassium carbonate (4.89 g, 35.4i mmol) in water (iO mL). The solution was degassed with argon for i5 minutes followed by the addition of iibis(diphenylphosphino)ferrocene palladium (II) dichloride (578 mg, 0.7i mmol). The reactionwas heated to iioC for i6 hours before cooling and diluting with EtOAc (300 mL). The organic solution was washed with water (2 x iOO mL), brine (75 mL), dried over sodium sulphate and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 0-4% MeOH in DCM to afford the title compound (i g, 23%).1H NMR (400 MHz, DMSO-d6): O ppm 3.66 (5, 3H), 5.25 (5, 2H), 7.20 (d, iH), 7.34 (t, iH), 7.4i(t, 2H), 7.50-7.54 (m, 4H), 7.59-7.6i (m, 2H), 7.77 (dd, iH), 8.i5 (d, iH). MS mlz 308 [M+H]

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; PFIZER LIMITED; SKERRATT, Sarah Elizabeth; BAGAL, Sharanjeet Kaur; SWAIN, Nigel Alan; OMOTO, Kiyoyuki; ANDREWS, Mark David; WO2015/92610; (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. 7189-69-7, name is 1,1′-Sulfonyldiimidazole, This compound has unique chemical properties. The synthetic route is as follows., name: 1,1′-Sulfonyldiimidazole

General procedure: A solution of 500 mg (4.46 mmol) of 2-fluorophenol 1.769 g (8.92 mmol) of 1,1?-sulfonyldiimidazole in 15 mL of tetrahydrofuran was treated with 727 mg (2.23 mmol) of cesium carbonate. The reaction was stirred for 12 h, concentrated, and the residue was partitioned between the ethyl acetate and water (10 mL each). The organic layer was washed sequentially with saturated ammonium chloride solution and brine. After drying over the anhydrous sodium sulfate, the organic layer was concentrated and chromatographed on silica with 1:5 ethyl acetate / hexane as the eluant to afford 880 mg (90%) of 11bas a clear oil:

According to the analysis of related databases, 7189-69-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yang, Baocheng; Sun, Zhexun; Liu, Changzhi; Cui, Yan; Guo, Zhilei; Ren, Yuwei; Lu, Zhijian; Knapp, Spencer; Tetrahedron Letters; vol. 55; 49; (2014); p. 6658 – 6661;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1849-01-0, These common heterocyclic compound, 1849-01-0, name is 1-Methyl-1H-benzo[d]imidazol-2(3H)-one, 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 69 1,3-Dihydro-1-methyl-3-(2-propynyl)-2H-benzimidazol-2-one potassium tert.-butoxide, 2.1 g (18.5 mmol). was added to a solution of 2.5 g (16.9 mmol) of 1,3-dihydro-1-methyl-2H-benzimidazol-2-one in 25 ml of dimethylformamide. After stirring under nitrogen for 15 minutes, 2.21 g (18.5 mmol) of propargyl bromide was added and the mixture was stirred at room temperature for 30 minutes. It was diluted with ice-water and the precipitate was filtered off washed with water and sucked dry. The crude product was passed over silica gel using 10% (v/v) of ethyl/acetate in methylene chloride for elution. Crystallization from ethyl acetate/hexane gave colorless crystals of 1,3-dihydro-1-methyl-3-(2-propynyl)-2H-benzimidazole-2-one with m.p. 110-112.

The synthetic route of 1849-01-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoffmann-La Roche Inc.; US4959361; (1990); 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. 87941-55-7, name is 4-Bromo-1-trityl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 87941-55-7

4-(3-Cyanophenyl)-1-(2-pyridyl)-1H-imidazole A mixture of 4-bromo-1-trityl-1H-imidazole (0.2g, 0.51 mmol), 3-cyanophenylboronic acid (0.11 g, 0.77 mmol), and Pd(PPh3)4 (0.06g, 0.05 mmol) in a solution of ethylene glycol dimethyl ether (2 mL) and 2M sodium carbonate (2 mL) was heated in a sealed vial overnight at 120 C. After cooling, the reaction mixture was diluted with dichloromethane (30 mL) and washed with water (50 mL) and brine (30 mL). The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Silica gel chromatography of the crude residue using 2% ethyl acetate in hexanes afforded 0.07 g (34%) 4-(3-cyanophenyl)-1-trityl-1H-imidazole as white foam. A solution of 4-(3-cyanophenyl)-1-trityl-1H-imidazole (0.07 g, 0.17 mmol) in tetrahydrofuran (1.36 mL) was treated with 2N hydrochloric acid (0.68 mL) and the resulting mixture was heated at reflux for 45 minutes. After cooling the reaction mixture was concentrated in vacuo and the residue dissolved in dichloromethane (20 mL). The organic phase was successively washed with 1N sodium hydroxide (10 mL), water (20 mL) and brine (20 mL). The organic solution was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Silica gel chromatography of the residues using 3% methanol in dichloromethane afforded 0.02 g (72%) of 4-(3-cyanophenyl)imidazole as a white solid. A solution of 4-(3-cyanophenyl)imidazole (0.02 g, 0.11 mmol) in N-methylpyrrolidinone (0.5 mL) was treated with 2-bromopyridine (1.05 mL, 11.1 mmol) and the reaction mixture heated overnight at 160 C. After cooling the reaction mixture was diluted with dichloromethane (40 mL) and the organic phase was successively washed with water (10*50 mL) and brine (50 mL). The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Silica gel chromatography using 30% ethyl acetate in hexanes afforded 2.5mg (9%) of 4-(3-cyanophenyl)-1-(2-pyridyl)-1H-imidazole, as an off-white solid.

According to the analysis of related databases, 87941-55-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wagenen, Bradford Van; Stormann, Thomas M.; Moe, Scott T.; Sheehan, Susan M.; McLeod, Donald A.; Smith, Daryl L.; Isaac, Methvin Benjamin; Slassi, Abdelmalik; US2003/55085; (2003); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem