Month: July 2021

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. 7189-69-7, name is 1,1′-Sulfonyldiimidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 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:

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:
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

Synthetic Route of 288-32-4, These common heterocyclic compound, 288-32-4, name is 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.

General procedure: Heterocycle (0.1 mol) was added into a solution of EtONa (8.16 g, 0.24 mol) in EtOH (30 mL) heated to reflux. After the solution was stirred for 30 min, 2-chloroethanol (8 g, 0.2 mol) was added dropwise. The resulting suspension was filtered, and the residue was concentrated by vacuum. The crude product was purified by column chromatography on silica gel to yield the desired product. (Rf = 0.3 (EA/ CH3OH= 5:1). The esterification procedure was the same as that in the synthesis of N series.

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

Reference:
Article; Hong, Fengying; Xia, Zhengce; Zhu, Dezhao; Wu, Hongxiang; Liu, Jianhui; Zeng, Zhuo; Tetrahedron; vol. 72; 10; (2016); p. 1285 – 1292;,
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. 75370-65-9, name is 4-Amino-1H-benzo[d]imidazol-2(3H)-one, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 4-Amino-1H-benzo[d]imidazol-2(3H)-one

Preparation of 1-(4-(trifluoromethyl)benzyl)-3-(2,3-dihydro-2-oxo-1H-benzo[d]imidazol-4-yl)urea Commercially available 4-trifluoromethylbenzylamine (0.5 ml, 3.5 mmol) was dissolved in 20 ml of AcOEt and at OC triphosgene (1 g, 3.5 mmol) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 5 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (5 ml) of compound 1a (350mg, 2.33mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt 9.5 / MeOH 0.5). The solvent was evaporated and the crude was dissolved in AcOEt (30ml) and washed with water (1 X 20ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 290mg of a white solid. Yield = 36% 1HNMR (DMSO, 400 MHz) delta 4.40 (2H, d, J = 6 Hz), 6.62 (1H, d, J = 7.2 Hz), 6.84 (2H, m), 6.96 (1H, d, J = 8 Hz), 7.54 (2H, d, J = 8 Hz), 7.70 (2H, d, J = 8.4 Hz), 8.30 (1H, s), 9.99 (1H, bs), 10.60 (1H, bs); [M+1] 351.1 (C16H13F3N4O2 requires 350.3).

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 75370-65-9.

Reference:
Patent; Pharmeste S.r.l.; EP2377850; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 71759-89-2, A common heterocyclic compound, 71759-89-2, name is 5-Iodo-1H-imidazole, molecular formula is C3H3IN2, 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.

1) 4-Iodo-1-[(4-methylphenyl)sulfonyl]-1H-imidazole 4-Methylbenzenesulfonyl chloride (5.40 g) was added to a chloroform (50 mL) and pyridine (4.17 mL) solution that contained 4-iodo-1H-imidazole (5.00 g) under cooling in an ice bath, and the obtained solution was then stirred for 2 hours. Thereafter, the reaction solution was added to water, and the obtained mixture was then extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and was then concentrated under a reduced pressure. The obtained solid was recrystalllized from ethyl acetate-hexane, so as to obtain the title compound (7.64 g) in the form of a colorless solid. 1H NMR (600 MHz, CHLOROFORM-d) delta ppm 2.45 (s, 3H) 7.35 (d, J=1.38 Hz, 1H) 7.37 (d, J=8.25 Hz, 2H) 7.82 (d, J=8.25 Hz, 2H) 7.86 (d, J=1.38 Hz, 1H)

The synthetic route of 71759-89-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD.; Nakamura, Toshio; Sakagami, Kazunari; Konishi, Kazuhide; Yamamoto, Kanako; Masuda, Seiji; Matsuda, Yohei; Okada, Kumiko; Shibata, Tsuyoshi; Ohta, Hiroshi; Yasuhara, Akito; Kawamoto, Hiroshi; Amada, Hideaki; Urabe, Hiroki; Nishikawa, Rie; Kashiwa ASHIWA, Shuhei; US2013/137865; (2013); A1;,
Imidazole – Wikipedia,
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. 1403474-70-3, name is Ethyl 2-ethoxy-1-((2′-(5-oxo-2,5-dihydro-1,2,4-oxadiazol-3-yl)-[1,1′-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate, A new synthetic method of this compound is introduced below., category: imidazoles-derivatives

Compound (5B) 5 g, placed in a reaction flask, adding ethanol 30ml, was added dropwise 2.5mol / L sodium hydroxide 13ml, 73-75 1.6 hours the reaction.After completion of the reaction, cooled to room temperature, the solution was added dropwise to the acidic water pH = 3-4, to precipitate a white solid 4.2g, 89.3%.

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; Shanghai Institute of pharmaceutical industry; Wang, Xiaomei; Sui, Qiang; Tang, Chao; Ouyang, Qunxiang; Shi, Huilin; Liu, Shuai; (18 pag.)CN103664920; (2016); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

2466-76-4, name is 1-(1H-Imidazol-1-yl)ethanone, 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. Product Details of 2466-76-4

General procedure: Nucleoside/nucleotide (2; 100 mM) and N-acetyl imidazole (1a;10 equiv) were dissolved in water (pH 8; adjusted with 4 MNaOH). The solution was incubated at r.t. for 4 h, and NMR spectra were periodically acquired. The product was purified byreverse-phase (C18) flash coumn chromatography (eluted at pH4 with 100 mM NH4HCO2/MeCN = 98:2 to 80:20). The fractions containing 5 were lyophilised to yield a white powder.

The synthetic route of 2466-76-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Fernandez-Garcia, Christian; Powner, Matthew W.; Synlett; vol. 28; 1; (2017); p. 78 – 83;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 716-79-0, name is 2-Phenyl-1H-benzo[d]imidazole, belongs to imidazoles-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 716-79-0, name: 2-Phenyl-1H-benzo[d]imidazole

Example 18 Preparation of Methyl 2-(2-phenyl-1H-benzo[d]imidazol-1-yl)acetate (S18) To a suspension of 2-phenyl benzimidazole (0.32 g, 1.6 mmol) in acetonitrile (5 mL) was added caesium carbonate (0.80 g, 2.5 mmol) and methyl bromoacetate (0.16 mL, 1.7 mmol). The reaction mixture was stirred at room temperature for 3 hours and concentrated in vacuo. The residue was suspended in a mixture of CH2Cl2 and sat. NaHCO3 (vol percent 50:50, 15 mL). The aqueous layer was reextracted with CH2Cl2 (2 x 20 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated in in vacuo to afford the product (0.40 g, 1.5 mmol, 91 percent). 1H NMR (400 MHz, DMSO-d6) delta 7.77 – 7.63 (m, 3H), 7.63 – 7.44 (m, 4H), 7.33 – 7.09 (m, 2H), 5.21 (s, 2H), 3.64 (s, 3H). 13C NMR (101 MHz, DMSO-d6) delta 169.40, 153.91, 143.08, 136.91, 130.57, 130.51, 129.62, 129.53, 123.45, 123.00, 119.87, 111.36, 53.17, 46.57. LC-MS (ESI): calcd for C16H14N2O2: 267.11280 [M+H]+, found: 267.18 [M+H]+; HR-MS found 267.11311 [M+H]+.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Max-Planck-Gesellschaft zur Foerderung der Wissenschaften e.V.; Waldmann, Herbert; Triola, Gemma; Wittinghofer, Alfred; Shehab, Ismail; Bastiaens, Philippe; Vartak, Nachiket; Papke, Bjoern; Zimmermann, Gunther; EP2698367; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 25676-75-9, name is 4-Bromo-1-methylimidazole, belongs to imidazoles-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 25676-75-9, HPLC of Formula: C4H5BrN2

To a solution of (4S)-6,8-dichloro-2-methyl-4-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,2,3,4-tetrahydroisoquinoline (50 mg) obtained in Reference Example 3-2 in dioxane (1.0 mL) and water (0.25 mL), 4-bromo-1-methyl-1H-imidazole (14 mg), tri(2-furyl)phosphine (17 mg), cesium carbonate (78 mg), and tris(dibenzylideneacetone)dipalladium(0) (11 mg) were added in a nitrogen gas atmosphere, and the mixture was stirred at 90C for 1 day.The reaction solution was allowed to cool, and then, water was added thereto, followed by extraction with ethyl acetate.The organic layer was dried over anhydrous magnesium sulfate and filtered, and then, the filtrate was concentratedunder reduced pressure. The obtained residue was purified by preparative LC-MS (LC (Agilent 1260), ESIMS (6130Quadrupole, ESI), column (YMC-Actus Triart 5 mm C18 50 x 30 mm), mobile phase (0.1% formic acid in H2O:0.1%formic acid in CH3CN = 95:5 ? 50:50 ? 5:95), 50 mL/min.) to obtain the title compound (3.6 mg, yield: 6.7%) as acolorless oil substance. 1H NMR (300 MHz, CD3OD) delta ppm 2.60 (s, 3H), 2.80 (dd, J=11.8, 9.8Hz, 1H), 3.17-3.26 (m, 1H), 3.62-3.71 (m, 1H),3.76 (s, 3H), 4.01-4.12 (m, 1H), 4.37 (dd, J=9.8, 5.8Hz, 1H), 6.79-6.83 (m, 1H), 7.07 (d, J=7.6Hz, 1H), 7.31-7.38 (m,2H), 7.46 (s, 1H), 7.54-7.69 (m, 3H). MS (+): 372 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-1-methylimidazole, and friends who are interested can also refer to it.

Reference:
Patent; Taisho Pharmaceutical Co., Ltd.; KURODA, Shoichi; KAWABE, Kenichi; USHIKI, Yasunobu; OHTA, Hiroshi; UNEUCHI, Fumito; SHIBATA, Tsuyoshi; TABUSE, Hideaki; MUNETOMO, Eiji; CHONAN, Sumi; (140 pag.)EP3173408; (2017); A1;,
Imidazole – Wikipedia,
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. 3012-80-4, name is 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde, A new synthetic method of this compound is introduced below., Formula: C9H8N2O

0.25 M stock solutions of amines (II) and aldehydes (III) in DCE were prepared. When applicable, the aldehyde salt forms were neutralized by addition of 4 equivalents of DIPEA. A 0.25 M fine suspension of NaBH(OAc)3 in anhydrous DMF/ DCE mixture (20/80) was prepared. To each vial was added 0.2 mL of a solution of amine (II) follwed by 0.2 mL of a solution of aldehyde (III) and 0.5 mL of the NaBH(OAc)3 suspension to each vial. The vials were capped and shaken at room temperature for 16 h. Additional 0.5 mL of the NaBH(OAc)3 suspension was added to each vial, the vials were vortexed, capped, and shaken at room temperature for 16 h. The solvent was removed under reduced pressure. 1 mL of DMSO and 0.1 mL of water were added to each vial. The samples were vortexed for 1 h. 0.05 mL of concentrated NH4OH was added to each vial. The samples were filtered and directly submitted to HPLC purification.

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 PRODUCTS INC.; WO2008/12623; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 16681-59-7, 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. 16681-59-7 name is 2-Bromo-1-methyl-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.

General procedure: Reactions were carried out in a Bohdan XT 24 position block using the appropriate halide indicated.2M Sodium carbonate (0.680 mL, 1.36 mmol) was added to a stirred mixture of 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazolo[1,5-a]pyridine (10, 151 mg, 0.62 mmol), the appropriate halide (0.74 mmol) and bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (Pd(Amphos)Cl2) (26.3 mg, 0.04 mmol) in DME (4 mL) under nitrogen. The resulting mixture was stirred at 80 C for 4 h, allowed to cool, diluted with water (10 mL), extracted with EtOAc (2×25 mL) and the organic layer was evaporated to afford crude products. Unless otherwise stated the crude product was purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5 mu silica, 19 mm diameter, 100 mm length, 5-95% MeCN/1% NH3 in H2O).

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

Reference:
Article; Bethel, Paul A.; Campbell, Andrew D.; Goldberg, Frederick W.; Kemmitt, Paul D.; Lamont, Gillian M.; Suleman, Abid; Tetrahedron; vol. 68; 27-28; (2012); p. 5434 – 5444;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem