Tag: M.W=100-200

Reference of 71759-89-2, 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. 71759-89-2, name is 5-Iodo-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 4-iodoimidazole (50 g, 258 mmoles) in DMF (500 ml) was added triethyl amine (37.7 ml, 270.6 mmoles) and than triphenylmethyl chloride (69.7 g, 250 mmoles). After stirring at room temperature for 48 hours, the solution was poured into ice water (2.5 L). The solid was filtered and pumped on for several hours to yield the crude compound. Ethyl ether (200 ml) was added to the crude compound and the solution was filtered to yield 4-IODO-1-TRITYL-LH-IMIDAZOLE (104.1, 93%) as a white solid. ME (437)

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

Reference:
Patent; CHIRON CORPORATION; WO2004/96822; (2004); A2;,
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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. 36947-68-9, name is 2-Isopropyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 36947-68-9

Example 47 Production of 2-[2-(2-Isopropylimidazol-1-yl)ethyl]isoindole-1,3-dione. N-(2-Bromoethyl)phthalimide (12.7 g, 50 mmol) and anhydrous potassium carbonate (6.9 g, 50 mmol) were added to a DMF (100 mL) solution of 2-isopropylimidazole (5.0 g, 45 mmol), and the mixture was stirred at 100C for 14 hours. The reaction mixture was poured into ice water, and extracted with ethyl acetate. An organic layer was dried over anhydrous sodium sulfate. Thereafter, the residue obtained by distilling off the solvents under a reduced pressure was purified with silica gel column chromatography (PSQ100B, chloroform : methanol = 100:1), to give the captioned compound (2.8 g, 22%) as an oily product. 1H-NMR (DMSO-d6) delta: 1.12 (d, J=6.7 Hz, 6H), 2.90-3.00 (m, 1H), 3.88 (t, J=6.3 Hz, 2H), 4.18 (t, J=6.3 Hz, 2H), 6.68 (s, 1H), 6.93 (s, 1H), 7.84-7.86 (m, 4H).

According to the analysis of related databases, 36947-68-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nippon Zoki Pharmaceutical Co., Ltd.; OOKUBO, Tomohiro; NAKAMURA, Ko; NAKAZAWA, Yoshitaka; NANBA, Hiroyoshi; YOSHIDA, Hiroyuki; EP2940003; (2015); A1;,
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Application of 4857-06-1, 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. 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 2-chloro-1H-benzo[d]imidazole (1.0 eq.) and ethanolamine (10 eq.) was heated to 200 C for 30 min by use of microwave irradiation. After the reaction was completed, the reaction mixture was cooled down to room temperature. The precipitated solid was filtered and washed with water to give desired product 2b. White solid (96% yield); mp 177.4 C; 1H NMR (400 MHz, CD3OD) delta 7.20-7.18 (m, 2H), 6.97-6.95 (m, 2H), 3.75 (t, J = 5.6 Hz, 2H), 3.49(t, J = 5.4 Hz, 2H); LRMS (electrospray) m/z (M+H)+ 178.

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

Reference:
Article; Oh, Sangmi; Kim, Sungbum; Kong, Sunju; Yang, Gyongseon; Lee, Nakyung; Han, Dawoon; Goo, Junghyun; Siqueira-Neto, Jair L.; Freitas-Junior, Lucio H.; Song, Rita; European Journal of Medicinal Chemistry; vol. 84; C; (2014); p. 395 – 403;,
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Synthetic Route of 2466-76-4, The chemical industry reduces the impact on the environment during synthesis 2466-76-4, name is 1-(1H-Imidazol-1-yl)ethanone, I believe this compound will play a more active role in future production and life.

Triethylamine (217 mg, 2.15 mmol), followed by 1-acetylimidazole (95 mg, 0.86 mmol), was added to a solution of the product from step 2 (200 mg, 0.43 mmol) in methylene chloride (5 mL). The reaction mixture was stirred at room temperature for 16 h. The solvent was removed under reduced pressure. The residue was dissolved in methanol (6 mL) and water (3 mL) and treated with potassium carbonate (300 mg, 2.17 mmol). The reaction mixture was stirred at room temperature for 2 h. The solvent was removed under reduced pressure. The residue was acidified with 1 N hydrochloric acid and extracted with ethyl acetate. The combined extracts were washed with saturated sodium chloride, and dried (sodium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica gel, 0-5percent methanol/methylene chloride provided the desired product (85 mg, 49percent) as a white foam. ESI MS m/z 407 [C2, H24F2N204 + H] + ; HPLC (Phenomenex Luna C18 (2) Column, 150 x 4.6 mm, 5R ; A: 0.05percent TFA in 95: 5 H20/CH3CN ; B: 0.05percent TFA in 5: 95 H20/CH3CN ; Gradient: 30-100percent B over 15 min; flow 1.0 mUmin ; Detection: 254 nm) 98.0percent (AUC), tR = 7.01 min. Anal. Calc’d for C21H24F2N2O4No.O. 25 H20 : C, 61.38 ; H, 6.01 ; N, 6.82 ; found: C, 61.60 ; H, 5.68 ; N, 6.59.

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-(1H-Imidazol-1-yl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; WO2005/87714; (2005); A2;,
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Related Products of 78581-99-4, A common heterocyclic compound, 78581-99-4, name is 5,6-Difluorobenzimidazole, molecular formula is C7H4F2N2, 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.

CuBr 6 mg (0.04 mmol), TEMPO 5 mg (0.03 mmol), compounded in a 25 mL Schlenk reaction tube5,6-difluorobenzimidazole 62 mg (0.4 mmol),28 mg (0.2 mmol) of salicylic acid (0.2 mmol) and p-xylene (0.5 mL), followed by 33 muL of pyridine (0.4 mmol) were added and the reaction was stirred at 120C for 36 hours under reflux.Cool to room temperature, transfer all to a 25 mL flask, spin off the solvent on a rotary evaporator, add an appropriate amount of silica gel to spin dry, and then use a 300-400 mesh silica gel column. The developing solvent used is petroleum ether:ethyl acetate=16: 1 to 6:1, that is, compound III-9 26mg, yield 48%; white solid

The synthetic route of 78581-99-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Southwest University; Cai Guixin; Xie Dan; (14 pag.)CN107955020; (2018); A;,
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30148-21-1, name is Ethyl 1-methyl-1H-imidazole-2-carboxylate, 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. HPLC of Formula: C7H10N2O2

A solution of the methylimidazole (3.2 mL, 40.0 mmol) in 30 mL de CH3CN:Et3N (2:1) was cooled to -30 C and quickly added to a previously prepared solution of ethyl chloroformiate (7 mL, 66.0 mmol) in 10 mL of CH3CN. The mixture was stirred for 15h at rt. The solvents were removed under reduced pressure; the crude was re-dissolved in water (20 mL) and extracted with chloroform (3 ¡Á 20 mL). The organic fractions were dried and concentrated, and the resulting residue was purified by flash cromatography (aluminum oxide, 90% MeOH) to give 3.72 g of a crude ester residue which was directly used for the next step. A solution of this residue (1.5 g, 9.74 mmol) in 15 mL of aqueous NaOH (1 M) was refluxed for 1 h. The resulting mixture was acidified to pH 2.0 using HCl 10% (aprox.15 mL) and lyophilized. The crude was dissolved in MeOH and concentrated underreduced pressure to give 12 as a slighlty pink solid (1.2 g, 98%).

The synthetic route of 30148-21-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jimenez-Balsa, Adrian; Dodero, Veronica I.; Mascarenas, Jose L.; Tetrahedron; vol. 69; 36; (2013); p. 7847 – 7853;,
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Electric Literature of 5465-29-2, 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 5465-29-2 as follows.

General procedure: To the reaction vessel containing benzimidazole or imidazole (1mmol), alkyl halide (1mmol), 50% NaOH (0.5mL) and anionic surfactant sodium dodecyl sulfate (5mol%) was added and the reaction mixture was vigorously stirred at room temperature or 60C. After the completion of reaction (TLC) followed by standard workup using ethyl acetate as extracting solvent the crude product was purified over silica-gel (60-120 mesh) using ethyl acetate-hexane (3:7) as eluent to afford pure products. Identities of the products were judged by the comparison of melting point, IR data, 1H NMR, 13C NMR and HRMS analyses.

According to the analysis of related databases, 5465-29-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Chakraborty, Ankita; Debnath, Sudipto; Ghosh, Tanmoy; Maiti, Dilip K.; Majumdar, Swapan; Tetrahedron; vol. 74; 40; (2018); p. 5932 – 5941;,
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Related Products of 1003-21-0, These common heterocyclic compound, 1003-21-0, name is 5-Bromo-1-methyl-1H-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.

Ethylmagnesium bromide (3.0 M in diethyl ether, 21.5 mL, 64.4 mmol) was added via syringe over a period of several minutes in an ice bath under nitrogen atmosphere to a solution of 5-bromo-1-methyl-1H-imidazole G, 64.4 mmol). A white precipitate was formed upon addition. The mixture was removed from the ice bath, stirred for 20 min and then cooled again in an ice bath before addition of 4-chloro-N-methoxy-N-methylbenzamide (10.7 g, 53.6 mmol, intermediate 1: step a) . The resulting white suspension was stirred at room temperature overnight. The reaction was quenched by the addition of a saturated aqueous NH4Cl solution and diluted with water. The mixture was partially concentrated, the THF was removed and diluted with DCM. The mixture was acidified to pH 1 with 1 N HCl aqueous solution and then neutralized with saturated aqueous NaHCO3 solution. The phases were separated and the aqueous phase further extracted with DCM. The organic extracts were washed with water, then dried (Na2SO4), filtered and concentrated to give a white solid. The crude product was triturated with a mixture of EtOAc: heptane (1: 1, 150 mL). The precipitated solid was collected by vacuum filtration and washed with heptane to give 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, N.V; Leonardo, Christie.A; Barubay, Kent; Edward, James P.; Kirsten, Kevin D.; Kumar, David A.; Maharupe, Uma; Nishimura, Rachel; Urbanski, Modu; Venkatesan, Hariharan; Wang, Ai Hua; OhLynn, Ronald L.; Woods, Craig R.; Fourier, Anne; Shu, Jia Hu; Cummings, Maxwell D.; (50 pag.)KR2016/70823; (2016); A;,
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Imidazole | C3H4N2 – PubChem

137049-00-4, name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, 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: 137049-00-4

To a solution of intermediate 2.40 (20. mg, 0.078 mmol) and triethylamine (30 muL, 0.2 mmol) in dichloromethane (0.5 mL) at ambient temperature was added 1-methyl- 1H-imidazole-4-sulfonyl chloride (21 mg, 0.12 mmol). The resulting mixture was stirred for 18 h, then diluted with wet dimethyl sulfoxide (0.5 mL), filtered through Celite and purified via mass-directed isolation using ultra-performance liquid chromatography (21 mg, 68% yield).1H NMR (500 MHz, Acetonitrile-d3) d 8.64 (s, 1H), 7.70 (dd, J = 11.8, 2.4 Hz, 1H), 7.62 (d, J = 1.4 Hz, 1H), 7.54 (d, J = 1.4 Hz, 1H), 7.37 (t, J = 8.6 Hz, 1H), 7.22 (ddd, J = 8.8, 2.4, 1.2 Hz, 1H), 3.80 (ddd, J = 11.7, 3.7, 1.9 Hz, 1H), 3.71 (s, 3H), 3.63 (d, J = 12.1 Hz, 1H), 2.65 (t, J = 11.1 Hz, 1H), 2.58 (ddt, J = 10.8, 7.2, 3.5 Hz, 1H), 2.52 (td, J = 11.9, 3.0 Hz, 1H), 1.93- 1.89 (m, 1H), 1.85- 1.74 (m, 1H), 1.65- 1.52 (m, 1H), 1.52- 1.39 (m, 1H); AMM (ESI) m/z 401.0858 [calc for C16H19ClFN4O3S (M+H)+ 401.0850].

The synthetic route of 137049-00-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE TRUSTEES OF THE UNIVERSITY OF PENNSYLVANIA; VAL-CHUM, LIMITED PARTNERSHIP; GRENIER, Melissa Carey; SMITH, Amos B., III; FINZI, Andres; DING, Shilei; CHAPLEAU, Jean-Philippe; (240 pag.)WO2020/28482; (2020); A1;,
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Imidazole | C3H4N2 – PubChem

68892-07-9, name is Methyl 2-mercapto-1-methyl-1H-imidazole-5-carboxylate, 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. Safety of Methyl 2-mercapto-1-methyl-1H-imidazole-5-carboxylate

To a mixture of example 159 (60 mg, 0.125 mmol, 1 equiv), methyl 2-mercapto-l-methyl-lH-imidazole-5-carboxylate (30.2 mg, 0,176 mmol, 1.4 equiv) and PPh3 (46.2 mg, 0.176 mmol. 1.4 equiv) in toluene (0.35 mL) at 0 C was added dropwise diethyl azodicarboxylate (40 % wt in toluene, 80 muEpsilon, 0, 176 mmol. 1.4 equiv). The mixture was stirred at rt for 3 h, concentrated, and then purified by column to give 79 mg (100%) of intermediate 161a as a white solid.

The synthetic route of 68892-07-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARDELYX, INC.; LEWIS, Jason, G.; REICH, Nicholas; CHEN, Tao; JACOBS, Jeffrey W.; CHARMOT, Dominique; NAVRE, Marc; FINN, Patricia; CARRERAS, Christopher; SPENCER, Andrew; WO2013/96771; (2013); A1;,
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Imidazole | C3H4N2 – PubChem