Month: May 2021

Application of 4857-06-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 4857-06-1 name is 2-Chloro-1H-benzo[d]imidazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

2-chloro- 1 -methyl- 1 H-benzo [d] imidazole[670] To a solution of 2-chloro- lH-benzo[d]imidazole (2.0 g, 13.1 mmol) in DMF(10 mL) was added NaH (0.63 g, 15.7 mmol) at 0 C under N2. After stirring for 30 min at 0 C, iodomethane (5.58 g, 39.3 mmol) was added and the mixture was stirred at room temperature for additional 1 hour. The reaction mixture was quenched with water (100 mL). The aqueous layer was extracted with EtOAc (3 x 20 mL). The combined organic layers were dried over a2S04, filtered, and concentrated to give the title compound (1.9 mg, 8.9 mmol, 67.9 % yield) as a white solid. MS: MS (M+H)+; XH NMR (400 MHz, CDC13): ? 7.71-7.68 (m, 1H), 7.31-7.27 (m, 3H), 3.79 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-1H-benzo[d]imidazole, and friends who are interested can also refer to it.

Reference:
Patent; ABBVIE INC.; BAYBURT, Erol K.; CLAPHAM, Bruce; COX, Phil B.; DAANEN, Jerome F.; GOMTSYAN, Arthur; KORT, Michael E.; KYM, Philip R.; VOIGHT, Eric A.; SCHMIDT, Robert G.; DART, Michael J.; GFESSER, Gregory; WO2013/62966; (2013); A2;,
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. 288-32-4, name is 1H-Imidazole, This compound has unique chemical properties. The synthetic route is as follows., Formula: C3H4N2

General procedure: CuCl (0.04mmol), L2 (0.08mmol), aryl idione or bromide (0.5mmol), imidazole or 1H-benzo[d]imidazole (0.75mmol), NaOH (1mmol), and DMSO (1mL) was added to a 5mL tube, then sealed. The mixture was stirred at 100C for certain time. After cooling to room temperature, the mixture was quenched with 10mL H2O and extracted with EtOAc (3×20mL). The combined EtOAc extracts were dried with anhydrous Na2SO4 and filtrated and the solvent was removed under reduced pressure. The residue was purified by flash column chromatography on silica gel with PE/EtOAc (from 2:1 (v/v) to pure EtOAc) as the eluent to afford the desired products.

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 288-32-4.

Reference:
Article; Liu, Ya-Shuai; Liu, Yan; Ma, Xiao-Wei; Liu, Ping; Xie, Jian-Wei; Dai, Bin; Chinese Chemical Letters; vol. 25; 5; (2014); p. 775 – 778;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 26663-77-4, These common heterocyclic compound, 26663-77-4, name is Methyl benzimidazole-5-carboxylate, 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 copper(I) acetate (2.4 mg, 0.020 mmol, 0.10 equiv.), benzimidazole 1a (23.6 mg, 0.20 mmol), and TMP iodonium(III) salt 2a (124.8 mg, 0.24 mmol, 1.2 equiv) in toluene (2 mL), triethylamine (56 mL, 0.4 mmol, 2 equiv) was added under a nitrogen atmosphere. The mixture was stirred for 5 min at room temperature, and the resulting solution was then heated to 50 C for 6 h (the reaction progress was monitored by TLC). After cooling to room temperature, the reaction was quenched by adding 5% aqueous ammonia solution (4 mL). The aqueous layer was extracted thrice with 20 mL of dichloromethane and the combined organic extracts were dried with anhydrous sodium sulfate. The organic solvents were then evaporated under reduced pressure, and the residue was purified by flash column chromatography on silica gel (eluent: n-hexane/ethyl acetate = 1/1) to obtain pure N-phenyl benzimidazole 3aa (38.5 mg, 0.198 mmol) in 99% yield

The synthetic route of 26663-77-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Koseki, Daichi; Aoto, Erika; Shoji, Toshitaka; Watanabe, Kazuma; In, Yasuko; Kita, Yasuyuki; Dohi, Toshifumi; Tetrahedron Letters; vol. 60; 18; (2019); p. 1281 – 1286;,
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. 3034-38-6, name is 5-Nitro-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., name: 5-Nitro-1H-imidazole

Example 268a 1-Methyl-4-nitro-1H-imidazole 268a To a mixture of 4-nitro-1H-imidazole (2.0 g, 17.7 mmol) and K2CO3 (3.67 g, 26.5 mmol) in acetonitrile (20 mL) was added iodomethane (1.3 mL, 3.0 g, 21.2 mmol) dropwise while stirring at room temperature. The resulting mixture was stirred at 60C overnight. It was then evaporated under reduced pressure and the residue was diluted with water (20 mL). The mixture was extracted with dichloromethane (2 X 20 mL). The combined extract was concentrated under reduced pressure and the residue was purified by silica-gel column chromatography eluting with 100:1 dichloromethane/methanol to afford 268a as a yellow solid (1.8 g, 82%). MS-ESI: [M+H]+ 128.1. 1H NMR (500 MHz, DMSO-d6) delta 8.37 (s, 1H), 7.82 (s, 1H), 3.76 (s, 3H).

According to the analysis of related databases, 3034-38-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F.Hoffmann-La Roche AG; CRAWFORD, James John; ORTWINE, Daniel Fred; WEI, BinQing; YOUNG, Wendy B.; EP2773638; (2015); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 1072-62-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1072-62-4 name is 2-Ethyl-1H-imidazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Taking 2 – ethyl imidazole 9.6g (0.1 muM), KOH 8.4g (0.15 muM), K2CO313 . 8g (0.1 muM) and tetrabutyl ammonium bromide 1.6g (0.005 muM) dissolved in 75 ml dichloromethane in, room temperature stirring 0.5h after, slow instillment bromine ethyl acetate 0.1 muM (11.2 ml), dropwise, 39 C reflow 8h, filtering, saturated salt water washed filtrate three times, dried with anhydrous sodium sulfate, 25 C distilling the organic phase to liquid droplet not to trickle out, obtaining oil object, i.e. the compound III intermediate 1

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Ethyl-1H-imidazole, and friends who are interested can also refer to it.

Reference:
Patent; Jiangsu Atomic Medical Institute; Qiu Ling; Lin Jianguo; Lv Gaochao; Li Ke; Peng Ying; Luo Shineng; Wang Shanshan; Zhao Xueyu; (27 pag.)CN106749406; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 35203-44-2,Some common heterocyclic compound, 35203-44-2, name is 1-Propyl-1H-imidazole, molecular formula is C6H10N2, 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 solution of 4-(bromomethyl)-6-methyl-coumarin (0.506 g, 2 mmol) in 30 mL of anhydrous dioxane, N-methylimidazole (0.164 g, 2 mmol) was added drop wise. The mixture was stirred for 48 h at 85 °C, after which a white solid obtained was filtered, washed with fresh anhydrous dioxane and dried. Then, to a methanolic solution (10 mL) of obtained bromide salt 1 (1 g, 2.5 mmol), 1-ethyl-3-((6-methyl-2-oxo-2H-chromen-4-yl)methyl)-3-propyl-1H-imidazolium bromide, KPF6 (0.691 g, 3.75 mmol) in 10 mL of water methanol (1:9 v/v) mixture is added drop wise under continuous stirring, white solid separates out. The reaction is allowed to stir for another 2 h after which excess water is added to the reaction mixture and filtered. This off-white solid was recrystallized by repeated precipitation using acetonitrile and diethyl ethyl ether mixture to afford pure imidazolium hexafluorophosphate salt 8.

The synthetic route of 35203-44-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Achar, Gautam; Shahini; Patil, Siddappa A.; Budagumpi, Srinivasa; Journal of Organometallic Chemistry; vol. 833; (2017); p. 28 – 42;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 33543-78-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 33543-78-1 name is Ethyl 1H-imidazole-2-carboxylate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Ethyl 1-(5-phthalimidomethyl-1oxoindan-2yl)imidazole-2-carboxylate can be synthesised in the following way: a suspension of 28.3 g of 2-bromo-5-phthalimidomethylindan-1-one and 21.4 g of ethyl imidazole-2-carboxylate in 700 ml of toluene is heated at reflux for 24 hours. The solution is evaporated under reduced pressure and the residue is taken up in 800 ml of saturated potassium carbonate solution and 800 ml of dichloromethane. The organic phase is separated by settling and the aqueous phase is extracted twice with 500 ml of dichloromethane. The organic phases are combined, washed six times with 800 ml of distilled water, dried over magnesium sulphate and evaporated under reduced pressure. After purification of the residue by flash chromatography on a silica column (eluent: dichloromethane/methanol (99/1 by volume)), 17.5 g of ethyl 1-(5-phthalimidomethyl-1oxoindan-2yl)imidazole-2-carboxylate are obtained in the form of a beige solid (1 H NMR spectrum in d6-DMSO and a few drops of CD3 CO2 D, T=300K, delta in ppm: 1.15 (3H, t, J=7 Hz, CH3), 3.35 and 3.70 (each 1H, respectively dd, J=6 and 16 Hz, and dd, J=9 and 16 Hz, CH2), 4.10 (2H, q, J=7 Hz, OCH2), 4.93 (2H, s, NCH2), 5.79 (1H, dd, J=6 and 9 Hz, NCH), 7.20 (1H, s, CH), 7.48 (1H, d, J=7 Hz, arom. CH), 7.53 (1H, s, arom. CH), 7.56 (1H, s, arom. CH), 7.72 (1H, d, J=7 Hz, arom. CH), between 7.80 and 7.95 (4H, m, phthal. H)).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 1H-imidazole-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Rhone-Poulenc Rorer S.A.; US5902803; (1999); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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 71759-88-1 as follows. Safety of 5-Iodo-1-methyl-1H-imidazole

In a 10 mL two-necked flask, 5-iodo-1-methyl-1H-imidazole (150 mg, 721 mumol, Eq: 1.00) was combined with DCM (3 ml) to give a colorless solution. Ethylmagnesium bromide (264 mul, 793 mumol, Eq: 1.1) was added at rt over 2 min (white precipitate). After stirring for 1 hr, the reaction mixture was cooled to 0 C., and a solution of 4-chlorobenzaldehyde (132 mg, 937 mumol, Eq: 1.3) in DCM (2 ml) was added dropwise, and the mixture was stirred at rt. TLC after 2 h indicated the absence of starting material. Work up: The reaction mixture was quenched with sat. NaHCO3 (10 mL) and extracted with AcOEt (2*20 mL). The organic layers were washed with H2O/NaCl sol., the organic layers were combined, dried over Na2SO4, and concentrated i. V. The product was precipitated from DCM, filtered and dried on h. V. MS (ESI): 223.1/225.0 [M+H]+.

According to the analysis of related databases, 71759-88-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HOFFMANN-LA ROCHE INC.; Aebi, Johannes; Amrein, Kurt; Hornsperger, Benoit; Kuhn, Bernd; Maerki, Hans P.; Mayweg, Alexander V.; Mohr, Peter; Tan, Xuefei; US2014/128429; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 14700-62-0, A common heterocyclic compound, 14700-62-0, name is 2-Benzyl-1H-imidazole, molecular formula is C10H10N2, 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.

13. 4-(2-Benzylimidazol-1-yl)benzyl alcohol Prepared from 2-benzylimidazol and ethyl 4-fluorobenzoate. MW: 264.33 1 H NMR (CDCl3) delta:7.45-7.37(m, 2H), 7.28-7.10(m, 8H), 7.00(d, J=1.5 Hz, 1H), 4.77(d, J=4.0 Hz, 2H), 4.02(s, 2H), 2.20-2.07(br, 1H).

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 Inc.; US5753682; (1998); A;,
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. 615-16-7, name is 2-Hydroxybenzimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 615-16-7

Sodium hydride (55% w/w dispersion in oil, 2.8 g) was added portionwise to a solution of 2,3-dihydrobenzimidazol-2-one (4.3 g) in DMF (100 ml) which had been cooled in an ice-water bath. The mixture was stirred at ambient temperature for 1.5 hours, during which period a further portion of DMF (50 ml) was added to aid the stirring of the reaction mixture. Methyl iodide (5 ml) was added and the mixture was stirred at ambient temperature for 16 hours. The mixture was evaporated and the residue was partitioned between ethyl acetate and water. The organic phase was washed with water and with brine, dried (MgSO4) and evaporated. The residue was purified by column chromatography using a 2:1 v/v mixture of toluene and ethyl acetate as eluent. There was thus obtained 1,3-dimethyl-2,3-dihydrobenzimidazol-2-one (3.14 g, 60%), m.p. 104-106 C.

The synthetic route of 615-16-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Imperial Chemical Industries PLC; ICI Pharma; US5179115; (1993); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem