Category: imidazoles-derivatives

Reference of 17325-26-7, 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. 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Intermediate 121 -(4-Cyano-2-fluoro-rhenyl)-1 H-imidazole-4-carboxylic acid methyl ester: A mixture of 3,4-difluorobenzonitrile (193 mg), 1 H-imidazole-4-carboxylic acid methylester (160 mg), and potassium carbonate (150 mg) in N-methyl-2-pyrrolidinone (4mL) is heated to 15000 for 30 mm in a microwave oven. After cooling to room temperature, the reaction mixture is diluted with water and ethyl acetate. The aqueous phase is extracted with ethyl acetate and the combined extracts are dried over MgSO4 and concentrated in vacuo. The residue is triturated with t-butyl methylether, filtered off, and dried to give the title compound. LC (method 4): tR = 0.78 mm; Mass spectrum (ESI): mlz = 246 [M+H]

The synthetic route of Methyl 1H-imidazole-5-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; NEUROCRINE BIOSCIENCES, INC.; NOSSE, Bernd; ECKHARDT, Matthias; HIMMELSBACH, Frank; LANGKOPF, Elke; ASHWEEK, Neil J.; HARRIOTT, Nicole; WO2014/19967; (2014); A1;,
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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. 5805-52-7, name is 1H-Benzimidazole-2-carboxamide, A new synthetic method of this compound is introduced below., Computed Properties of C8H7N3O

At room temperature, 3.0 g (18.6 mmol)1H-benzimidazole-2-carboxamide and 7.5 g (18.6 mmol)Lawson reagent placed in 250mL eggplant bottle,Add 150 mL of tetrahydrofuran to reflux at 66 C for 5 h.After the completion of the reaction, the solvent was evaporated to drynessWith methylene chloride dissolved, saturated sodium bicarbonate wash, saturated sodium chloride wash, the organic phase, anhydrous sodium sulfate drying, filtration, columnChromatography to obtain a white solid. Yield: 60.0%.

The synthetic route of 5805-52-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shenyang Pharmaceutical University; Zhao Linxiang; Liu Dan; Li Kun; Wang Shuxiang; Jing Yongkui; (21 pag.)CN106905241; (2017); A;,
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Synthetic Route of 288-32-4, A common heterocyclic compound, 288-32-4, name is 1H-Imidazole, molecular formula is C3H4N2, 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.

General procedure: To a stirred solution of 10 (1.00g, 4.00mmol) and K2CO3 (1.66g, 12.00mmol) in acetonitrile (20mL) was added dropwise diethylamine solution (1.20g, 16.00mmol) at room temperature for 2h. The solvent was evaporated in vacuo and the residue was then dissolved in EtOAc (50mL) and washed with water (20mL¡Á3), the organic layers were washed with brine, and dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure to provide the 11a (0.83g, 84.7% yield) as an off-white liquid. (0041) Then, a mixture of 11a (0.83g, 3.43mmol), bis(pinacolato)diboron (0.96g, 3.77mmol), PdCl2(dppf)-CH2Cl2 (0.084g, 0.103mmol) and potassium acetate (0.67g, 6.86mmol) in anhydrous 1,4-dioxane (15mL) was purged with argon and heated at 100C for 2.5h. The reaction was then treated with 6 (1.20g, 3.60mmol), 2.0M aqueous Na2CO3 (5mL) and another portion of PdCl2(dppf)-CH2Cl2 (0.084g, 0.103mmol), then heated at 110C for 12h under argon. The reaction mixture was cooled to room temperature, filtered, and concentrated. The final compound was purified by MPLC (ISCO CombiFlash purification system) (MeOH/DCM, eluted from 0% to 10%), The fractions were collected, concentrated to afford 12a (0.72g, 57.2% yield).

The synthetic route of 288-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Han, Jinsong; Chen, Ying; Yang, Chao; Liu, Ting; Wang, Mingping; Xu, Haojie; Zhang, Ling; Zheng, Canhui; Song, Yunlong; Zhu, Ju; European Journal of Medicinal Chemistry; vol. 122; (2016); p. 684 – 701;,
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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. 32673-41-9, name is 4-Imidazolemethanol hydrochloride, A new synthetic method of this compound is introduced below., name: 4-Imidazolemethanol hydrochloride

EXAMPLE I To thionyl chloride (170 ml, 2.35 m) stirred at room temperature there was added portion-wise over a ten minute period with exclusion of moisture, 64 g (0.48 m) of 4-hydroxymethylimidazole hydrochloride. With each addition vigorous evolution of gas occurred and occasional cooling by ice/water bath was necessary to keep the temperature below 30 C. The resulting greenish solution was stirred at 30 C. for an additional ten minutes until the gas evolution subsided. The temperature was then raised to 55+-5 C. for forty minutes during which time a thick gelatinous precipitate formed. The reaction mixture was cooled and excess thionyl chloride removed under reduced pressure at 30 C. The yellow residue was triturated with 100 ml of ether, collected and washed four times with 50 ml of ether. The product, a very pale yellow powder, was dried in a stream of air to give 70.88 g (96.5% yield) of 4-chloromethylimidazole hydrochloride m.p. 145-6 C. which was stored under refrigeration. C4 H6 N2 Cl2 requires 31.40% C, 3.95% H, 18.31% N and 46.34% Cl. Elemental analysis found 31.30% C, 4.01% H, 18.34% N and 47.17% Cl.

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; Polaroid Corporation; US4847383; (1989); A;,
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Related Products of 1219741-21-5, These common heterocyclic compound, 1219741-21-5, name is 5-Chloro-6-iodo-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.

Cs2CO3 (2.3 g, 7.08 mmol), followed by tert-hutyl bromoacetate (0.52 mL, 3.54 mmol), was added to a solution of 5- chloro-6-iodo-l,3-dib.ydro-2H-benzimidazole-2~thione (Intermediate 7, 1.1 g, 3.54 mmol) in THF (20 mL) at O0C. The reaction was stirred at rt for 0.5 h. Volatiles were removed and the residue was partitioned between EtOAc and water. Concentration afforded the desired product as a white power. LC-MS: calculated for C13H14ClIN2O2S 423.95, observed m/e 424.8 (M+H)+.

Statistics shows that 5-Chloro-6-iodo-1H-benzo[d]imidazole-2(3H)-thione is playing an increasingly important role. we look forward to future research findings about 1219741-21-5.

Reference:
Patent; MERCK SHARP & DOHME CORP.; METABASIS THERAPEUTICS, INC.; DANG, Qun; CHUNG, De Michael; GIBSON, Tony, S.; JIANG, Hongjian; CASHION, Daniel, K.; BAO, Jianming; LAN, Ping; LU, Huagang; MAKARA, Gergely, M.; ROMERO, F. Anthony; SEBHAT, Iyassu; WODKA, Dariusz; WO2010/51206; (2010); A1;,
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Imidazole | C3H4N2 – PubChem

Synthetic Route of 4856-97-7, 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. 4856-97-7, name is (1H-Benzoimidazol-2-yl)methanol belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Thionyl bromide is used for some brominations ofcertain ,-unsaturated carbonyls, and it also converts alcohols to alkyl bromides [21]. To asolution of I (5.92 g, 0.04 mol) in 75 mL cyclohexane as a nonpolar solvent and 2 mL N,Ndimethylformamideas a catalyst, was drop wise added thionyl bromide (5 mL).The addition ofN,N-dimethylformamide as a catalyst was found to accelerate the reaction significantly througha Vilsmeier?Haack type SOBr2?DMF complex [22]. The mixture was refluxed for 10 h. Theexcess of thionyl bromide was evaporated under vacuum and residue dissolved in cyclohexaneand washed with water (3¡Á50 mL). The organic layer was dried over sodium sulfate andevaporated to obtain the product (Scheme 1). Beige to dark yellow powder, m.p. 158-162 oC, 89.1percent yield. IR (KBr, cm-1): 3345 (N-H str), 3045 (Ar-C-H str), 2952 (aliphatic C-H str) , 1682(C=N str), 1448 (C=C str), 1292 (C-N str), 667 (C-Br); 1H-NMR (CDCl3, /ppm): 4.64 (s, 2H,CH2),4.89 (s, 1H, NH), 7.20-7.25 (m, 2H, Ar-H), 7.54-7.57 (m, 2H, Ar-H); 13C-NMR (CDCl3,/ppm): 45.1 (CH2-Br), 114.8 (benzimidazole, CH=), 121.6 (benzimidazole, CH=), 135.2(benzimidazole, C), 140.1 (N-C=N). Anal. calcd. for C8H7N2Br: C, 45.50; H, 3.31; N, 13.27percent.Found: C, 45.31; H, 3.28; N, 13.20percent. MS, m/z: 211[M]+.

The synthetic route of (1H-Benzoimidazol-2-yl)methanol has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ahmadi, Abbas; Bulletin of the Chemical Society of Ethiopia; vol. 28; 3; (2014); p. 451 – 456;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 4238-71-5, 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 4238-71-5 as follows.

To a cooled (-50 C) suspension of 1 -benzyl- lH-imidazole (1.58 g, 10.0 mmol) in anhydrous diethyl ether (50 mL) under nitrogen was added w-butyl lithium (2.5 M in hexanes, 4.0 mL, 10.0 mmol) dropwise. After being stirred for 20 min at -50 C, dry carbon dioxide (passed through Drierite) was bubbled into the reaction mixture for 10 min before it was allowed to warm up to 25 C. The heavy precipitate which formed on addition of carbon dioxide to the reaction mixture was filtered to yield a hygroscopic, white solid which was taken up in water (7 mL), acidified to pH = 3, cooled, and induced to crystallize with scratching. Filtration of this precipitate gave a white solid which was suspended in methanol, treated with IN HCl/diethyl ether (4 mL) and concentrated in vacuo. Lyophilization of the residue from water (5 mL) afforded the HC1 salt of Cap- 136 as a white solid (817 mg, 40%). 1H NMR (300 MHz, DMSO-d6) delta 7.94 (d, J= 1.5 Hz, 1H), 7.71 (d, J= 1.5 Hz, 1H), 7.50-7.31 (m, 5H), 5.77 (s, 2H); Rt = 0.51 min (Cond.-MS- W5); 95% homogenity index; LRMS: Anal. Calc. for [M+H C11H12N2O2: 203.08;found: 203.11.

According to the analysis of related databases, 4238-71-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PACK, Shawn, K.; TYMONKO, Steven; PATEL, Bharat, P.; NATALIE, JR., Kenneth, J.; BELEMA, Makonen; WO2011/59850; (2011); A1;,
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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. 89830-98-8, name is 5-Cyclopropyl-1H-imidazole, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H8N2

[0304] A mixture of Example 3j (600 mg, 2.4 mmol) and Example 3i (400 mg, 3.6 mmol), Cul (45 mg, 0.24 mmol), K3P04 (1 g, 4.8 mmol), 4,7-Dihydroxy-l, 10-phenanthroline(9 mg, 0.48 mmol), TBAB (386 mg, 1.2 mmol) in H20 (10 mL) under N2 was heated at 100¡ãC overnight. After cooling, the reaction mixture was filtered and concentrated under reduced pressure to give the crude and further purified by silica chromatography to give the product 200 mg as yellow solid.

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; FRONTHERA U.S. PHARMACEUTICALS LLC; JIN, Bohan; DONG, Qing; HUNG, Gene; (227 pag.)WO2018/151830; (2018); A1;,
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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. 75370-65-9, name is 4-Amino-1H-benzo[d]imidazol-2(3H)-one, A new synthetic method of this compound is introduced below., category: imidazoles-derivatives

Commercially available p-methylbenzylamine (0.88 ml, 6.97 mmol) was dissolved in 40 ml of AcOEt and at 0C triphosgene (2 g, lequiv.) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 20 ml of DMF. The solution of the isocyanate was added drop wise to a solution in DMF (10 ml) of compound la (1 g, 6.97 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt). The solvent was evaporated and the crude was dissolved in AcOEt (50 ml) and washed with water (1 X 30 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 350 mg of a white solid. Yield = 17% ‘HNMR (DMSO, 200 MHz) delta 6.61 (1H, dd, J = 7.6 Hz, J’ = 1.2 Hz), 6.70 (1H, t), 6.83 (1H, t, J = 8 Hz), 6.92 (1H, dd, J = 8 Hz, J’ = 1 Hz), 7.17 (4H, dd, J = 15.6 Hz, J’ = 8.2 Hz), 8.22 (1H, bs), 9.96 (1H, bs), 10.58 (1H, bs); [M+1] 297.1 (C16H16N4O2 requires 296.32).

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; PHARMESTE S.R.L.; NAPOLETANO, Mauro; TREVISANI, Marcello; PAVANI, Maria Giovanna; FRUTTAROLO, Francesca; WO2011/120604; (2011); A1;,
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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. Recommanded Product: 111851-98-0

General procedure: To a flask equipped with a stir bar and a condenser was added carboxaldehyde (4 mmol, 1.0 equiv), 1- triphenylphosphoranylidene)-2-propanone (4.2 mmol, 1.05 equiv), and toluene (8 mL). The reaction mixture was stirred at 70 C for 5 h. After completion, the reaction mixture was acidified to PH 3 with 1M HCl, and extracted with DCM (15 mL ¡Á 3). The aqueous layer was basified to PH 9 with sodium bicarbonate, and the resulting mixture was extracted with DCM (15 mL ¡Á 3). The DCM extracts from basic aqueous layer were combined, dried over anhydrous magnesium sulfate, and concentrated to give the corresponding (E)-4-(1-alkyl-1H-imidazol-2-yl)but-3-en-2-one.

The synthetic route of 1-Ethyl-1H-imidazole-2-carbaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Qiao-Hong; Yu, Kevin; Zhang, Xiaojie; Chen, Guanglin; Hoover, Andrew; Leon, Francisco; Wang, Rubing; Subrahmanyam, Nithya; Addo Mekuria, Ermias; Harinantenaina Rakotondraibe, Liva; Bioorganic and Medicinal Chemistry Letters; vol. 25; 20; (2015); p. 4553 – 4556;,
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Imidazole | C3H4N2 – PubChem