Month: June 2021

Electric Literature of 89532-38-7, A common heterocyclic compound, 89532-38-7, name is 2-Cyclopropyl-1H-imidazole, molecular formula is C6H8N2, 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.

To a mixture of ethyl 3-(5-(4-bromophenyl)-1-(4-carbamoyl-2-methylphenyl)-1H-pyrrol-2-yl)propanoate (455 mg, 1.0 mmol) and 2-cyclopropyl-1H-imidazole (17-3) (324 mg, 3.0 mmol, 3.0 eq.) in NMP (4 ml) was added 8-hydroxyquinoline (22 mg, 0.15 mmol, 0.15 eq.), Cu2O (282 mg, 0.1 mmol) and K2CO3 (166 mg, 1.2 mmol) and PEG-2000 (50 mg). The resulting mixture under N2 was irradiated under microwave at 128 C for 6.0 h, cooled to room temperature and diluted with THF (10 ml) and water (10 ml). The mixture was filtered and the resulting aqueous layer was extracted with EA (30 ml x 5). The combined organic layers were washed with brine (20 ml), dried over MgSO4, filtered, concentrated and purified by silica gel column chromatography (MeOH : CH2Cl2 = 1 : 15) to afford the desired compound as a yellow solid (190 mg, yield 39%).

The synthetic route of 89532-38-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sun, Xicheng; Qiu, Jian; Strong, Sarah A.; Green, Louis S.; Wasley, Jan W.F.; Blonder, Joan P.; Colagiovanni, Dorothy B.; Mutka, Sarah C.; Stout, Adam M.; Richards, Jane P.; Rosenthal, Gary J.; Bioorganic and Medicinal Chemistry Letters; vol. 21; 19; (2011); p. 5849 – 5853;,
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. 1546-79-8, name is 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone

1,8-diazabicyclo[5.4.0]undec-7-enium 5′-O-(tert-butyldiphenylsilyl)-2′-O-(tert-butyldimethylsilyl)uridine-3′-yl phosphonate (8u) (100 mumol) are dried by repeated co-evaporation with anhydrous pyridine and then dissolved in anhydrous pyridine (1 mL). N,N’-bis(2-oxo-3-oxazolidinyl)phosphinic acid chloride (BopCl; 500 mumol) is added and the mixture is allowed to stir for 5 minutes.To the mixture, a solution of amino alcohol (L-2) (100 mumol) dissolved in anhydrous pyridine (1 mL) was added dropwise by syringe and the mixture was stirred for 5 min under argon. 2′,3′-O-bis((tert-butyldimethylsilyl)uridine 9u is dried using repeated co-evaporation with anhydrous pyridine and dissolved in 100 mumol pyridine. Thereafter, the mixture is added via cannula to a solution of 2′,3′-O-bis(tert-butyldimethylsilyl)uridine 9u (100 mumol). After 10 minutes N-trifluoroacetylimidazole (CF3COIm; 200 mumol) is added. After an additional 30 seconds N,N’-dimethylthiuram disulfide (DTD; 120 mul) is added. After a further 3 minutes the mixture is dried in vacuo. Concentrated NH3-EtOH (3: 1, v / v, 10 mL) is added to the residue and the mixture is allowed to stir for 12 hours, then concentrated to dryness under reduced pressure. Thereafter, the mixture is diluted with CHCl3 (5 mL) and washed with 0.2 M phosphate buffer (pH 7.0, 5 mL). The aqueous layer is back-extracted with CHCl3 (2 × 5 mL). The organic layers are combined, dried over Na2SO4, filtered and concentrated to dryness under reduced pressure. The residue is purified by preparative TLC. The product was dissolved in CHCl3 (5 mL), washed with 0.2 M 1,8-diazabicyclo [5.4.0] undec-7-enium bicarbonate buffer (5 mL) and washed with CHCl3 (2 × 5 mL) Back extracted. Combine the organic layers, dry over Na2SO4, filter, concentrate and dry to give (SP)-10uu.

According to the analysis of related databases, 1546-79-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ONTORII INCORPORATED; VERDINE, GREGORY L; MEENA, MEENA; IWAMOTO, NAOKI; (250 pag.)JP2015/205910; (2015); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 583-39-1, 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. 583-39-1, name is 2-Mercaptobenzimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Benzyl chloride or 1-iodopropane, 89.25 mmol, and potassium carbonate, 170.0 mmol, were added to a solution of 85.0 mmol of 1,3-dihydro-2H-benzimidazole-2-thione in 140 mL of acetone. The mixture was refluxed for 3 h with stirring and poured into water with stirring to dissolve inorganic com-ponents. The precipitate was filtered off and washed with water and methanol. Compound 1b was dried and recrystallized from 20 mL of methanol. Compound 1a required no additional purification. Compound 1a. Yield 93%, colorless crystals, mp 180-181C. 1 H NMR spectrum, delta, ppm: 4.56 s (2H, CH 2 ), 7.07 t (2H, H arom , J = 4.0 Hz), 7.21 t (1H, H arom , J = 6.8 Hz), 7.28 t (2H, H arom , J = 7.2 Hz), 7.35-7.45 m (4H, H arom ), 12.04 br.s (1H, NH). Compound 1b. Yield 55%, colorless crystals, mp 151-152C. 1 H NMR spectrum, delta, ppm: 1.07 t (3H, CH 3 , J = 7.2 Hz), 1.80 sext (2H, CH 2 , J = 6.8 Hz), 3.25 t (2H, CH 2 , J = 7.2 Hz), 7.05 s (2H, H arom ), 7.37 s (1H, H arom ), 12.27 s (1H, NH).

The synthetic route of 2-Mercaptobenzimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kharaneko; Russian Journal of Organic Chemistry; vol. 54; 9; (2018); p. 1363 – 1368; Zh. Org. Khim.; vol. 54; 9; (2018); p. 1350 – 1354,5;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 32673-41-9, A common heterocyclic compound, 32673-41-9, name is 4-Imidazolemethanol hydrochloride, molecular formula is C4H7ClN2O, 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.

Step A Preparation of 1-Triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of 4-(hydroxymethyl)imidazole hydrochloride (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the title product as a white.

The synthetic route of 32673-41-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US6297239; (2001); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 3034-50-2, name is Imidazole-4-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C4H4N2O

To a mixture of 1H-imidazole-4-carbaldehyde (3.71 g, 38.6 mmol), 1-chloro-4-iodobenzene(13.81 g, 57.9 mmol), (1R,2R)-N1,N2-dimethylcyclohexane-1,2-diamine (1.10 g, 7.72 mmol),copper(l) iodide (0.368 g, 1.93 mmol) and cesium carbonate (25.2 g, 77 mmol) was added DMF (50 mL). The reaction was sealed and heated to 110 00 for 18 hours. The reaction mixture was then cooled to room temperature and diluted with a saturated solution of NH4CI.brown solid develops. Solid was collected, washed with water and air dried. Solid materialwas then dissolved in 10%MeOH:90%DCM solution and dried (Na2504), filtered and concentrated to afford a dark brown solid 1-(4-chlorophenyl)-1 H-imidazole-4-carbaldehyde (8.55 g, 41.4 mmol, 107 % yield). Material as used without further purification. LCMS m/z 207.1 (M + H), Rt 0.58 mm.Step 1

The synthetic route of 3034-50-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; CAFERRO, Thomas Raymond; CHEN, Zhuoliang; CHO, Young Shin; COSTALES, Abran Q.; LEVELL, Julian Roy; LIU, Gang; MANNING, James R.; SENDZIK, Martin; SHAFER, Cynthia; SHULTZ, Michael David; SUTTON, James; WANG, Yaping; ZHAO, Qian; WO2014/141104; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1003-21-0, 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. 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Ethylmagnesium bromide (3 M in Et2O, 0.0642 mL, 0.193 mmol) was added dropwise to a solution of 5-bromo-1-methyl-1H-imidazole (31.0 mg, 0.193 mmol) in DCM (1 mL) under a nitrogen atmosphere. The mixture was stirred at room temperature for 15 min, then was cooled to 0 C. A solution of (2,4-dichloro-3-phenylquinolin-6-yl)(3-methylisoxazol-5-yl)methanone (49.2 mg, 0.128 mmol, Intermediate 37, step b) in DCM (2 mL) was added via cannula. The mixture was stirred at room temperature for 2 hours. The reaction was quenched by addition of saturated aqueous NH4Cl and was diluted with water. The mixture was extracted three times with EtOAc. The organic phase was dried (Na2SO4), filtered, and concentrated. The crude product was purified by RP-HPLC (10-90% CH3CN-H2O, 0.1% TFA) to afford the title compound. 1H NMR (400 MHz, DMSO-d6) delta 8.99 (br. s., 1H), 8.39 (s, 1H), 8.10-8.25 (m, 2H), 7.83 (d, J=9.05 Hz, 1H), 7.47-7.63 (m, 3H), 7.36-7.47 (m, 2H), 7.27 (br. s., 1H), 6.38 (s, 1H), 3.52 (s, 3H), 2.24 (s, 3H); MS m/e 465.1 [M+H]+.

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

Reference:
Patent; Janssen Pharmaceutica NV; Leonard, Kristi A.; Barbay, Kent; Edwards, James P.; Kreutter, Kevin D.; Kummer, David A.; Maharoof, Umar; Nishimura, Rachel; Urbanski, Maud; Venkatesan, Hariharan; Wang, Aihua; Wolin, Ronald L.; Woods, Craig R.; Fourie, Anne; Xue, Xiaohua; Mirzadegan, Taraneh; Ganamet, Kelly; US2014/107097; (2014); 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. 86604-86-6, name is 2-Chloro-6-(trifluoromethyl)benzimidazole, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H4ClF3N2

Example 1 8-(5-(Trifluoromethyl)-1H-benzo[d]imidazol-2-yloxy)quinolin-2-ol A mixture of 2-chloro-5-(trifluoromethyl)-1H-benzo[d]imidazole (66 mg, 0.3 mol, prepared according to the procedure described in WO 2004/035549 A1), 2,8-dihydroquinoline (48 mg, 0.3 mmol, Fluka) and N,N-diisopropylethylamine (0.1 mL, 0.58 mmol, Aldrich) in EtOH (2 mL) was subjected to microwave irradiation at 180 C. with stirring for 60 min. The reaction mixture was allowed to cool to room temperature, the solvent was removed in vacuo and the residue was purified by silica gel chromatography, eluding with 80% EtOAc/hexane to give the title compound as an amorphous solid. MS (ESI, pos. ion) m/z: 346 (M+1).

According to the analysis of related databases, 86604-86-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Norman, Mark H.; Ognyanov, Vassil I.; Wang, Xianghong; US2006/160872; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 7098-07-9, name is 1-Ethyl-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. Recommanded Product: 1-Ethyl-1H-imidazole

To the dry 100 mL three-necked flask was added 6.3 g (10 mmol) of M2 ‘, 0.96 g (10 mmol) of 1-ethyl terephthalate, 50 mL of acetonitrile, reacted at room temperature for 4 days and TLC was used to monitor the reaction end. Washed with petroleum ether (100 mL x 3) to give a viscous liquid which was washed with ether (100 mL x 3), dried in vacuo for 24 h, To give 7.2 g of the title compound (B5) as a brown oily liquid in a yield of 99percent.

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

Reference:
Patent; Central China Normal University; Zhang Aidong; Zhang Tiejiang; Duan Jiang; Tu Haiyang; (22 pag.)CN107188869; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 51605-32-4, 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 51605-32-4 as follows.

Hydrolysis of ethyl-4-methyl-1H-imidazole carboxylate(7, 3.0 g, 19.5 mmol) was carried out in a basic medium offreshly prepared 2 M NaOH solution for 3 h. Neutralizationwith glacial acetic acid was performed after the completionof the reaction. The aqueous solvent was evaporated underreduced pressure and 10 mL of absolute ethanol was used tore-dissolve the white solid product. The reaction mixture wasfiltered off and the precipitate was dissolved several timeswith absolute ethanol and co-evaporation was performed toremove water traces. 4-Methyl-1H-imidazole-5-carboxylic acid(8) was obtained as a white solid with a yield of 87.8%.

According to the analysis of related databases, 51605-32-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Jasim, Suhair H.; Sheikha, Ghassan M. Abu; Abuzaid, Haneen M.; Al-Qirim, Tariq M.; Shattat, Ghassan F.; Sabbah, Dima A.; Ala, Samah A.; Aboumair, Mustafa S.; Sweidan, Kamal A.; Bkhaitan, Majdi M.; Chemical and Pharmaceutical Bulletin; vol. 66; 10; (2018); p. 953 – 958;,
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. 17289-20-2, name is Methyl 1-methyl-1H-imidazole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C6H8N2O2

To the solution of commercially available 4.3 g methyl 3-methylimidazole-4-carboxyIate in 100 mL THF at 23 C was added 7.4 g lithium tertbutoxide and reaction mixture was stirred at 23 C for 15 min. Then, 10.9 g N-bromosuccinimide (NBS) was added and reaction mixture was stirred at 23 C for additional 12 h. Reaction mixture was quenched with water and was basified with sat. NaHCC>3 solution to pH 14. The compound was extracted with EtOAc (20 mL x 3), combined organic layer was dried over Na2S04and concentrated under reduced pressure to get crude compound which was purified by column chromatography over silica gel using 30 % EtOAc in />heptane as an eluent to afford the title compound as off white solid (1.8 g; 27.0% yield).

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 17289-20-2.

Reference:
Patent; BASF SE; GOCKEL, Birgit; SOERGEL, Sebastian; KOERBER, Karsten; (152 pag.)WO2019/137995; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem