Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, 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 17325-26-7, SDS of cas: 17325-26-7

For methyl 1-tritylimidazole-4-carboxylate (6), trityl chloride(1.77 g, 6.35 mmol) was first stirred into a solution of 5 (0.80 g,6.3 mmol) in DMF (20 mL) under N2. NEt3 (0.98 mL, 7.0 mmol) wasthen added, and the mixture stirred for 16 h at r.t. before being pouredover ice; the cold mixture was then filtered and the isolated solid waswashed with H2O (2 × 5 mL), and then dried in vacuo at r.t. for 24 h.Yield: 2.01 g (86%). 1H NMR (CDCl3): delta 7.65 (s, 1H, H5-Im), 7.52 (s, 1H,H2-Im), 7.03-7.36 (m, 15H, Ph3C), 2.42 (s, 3H, CH3-Im). ESI-MS: 369(M+), 243 (CPh3). Anal. Calcd. for C24H20N2O2: C, 78.24; H, 5.47; N,7.60. Found: C, 78.35; H, 5.6; N, 7.4.

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, Methyl 1H-imidazole-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kennedy, David C.; James, Brian R.; Inorganic Chemistry Communications; vol. 78; (2017); p. 32 – 36;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

51605-32-4, name is Ethyl 5-methyl-1H-imidazole-4-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. Computed Properties of C7H10N2O2

Methyl 2-fluoro-5-nitrobenzoate (21.9 g, 0.11 mol) and ethyl 4-methyl-5-imidazole-carboxylate (15.4 g, 0.1 mol) were dissolved in DMSO (150 mL). Cesium carbonate (32.6 g, 0.1 mol) was added and the mixture was stirred at RT for 24 h. TLC analysis (ethyl acetate) showed a new spot with Rf 0.4. The reaction mixture was poured into ice water and left to stand for 3 hours. A precipitate could be seen at the bottom of the flask. The solid was isolated by filtration, after washing with water several times. The product (31.3 g) was obtained in yield 94percent. 1H NMR (300 MHz, CDCl3): dH 1.45 (3H, t, J = 7.1 Hz, COOCH2CH3), 2.33 (3H, s, NCCH3), 3.72 (3H, s, COOCH3), 4.39 (2H, q, J = 7.1 Hz, COOCH2CH3), 7.47 (1H, s, NCHN), 7.52 (1H, d, J = 8.6 Hz, CCHCHCNO2CH), 8.53 (1H, dd, J = 8.6 and 2.8 Hz, CCHCHCNO2CH), 8.94 (1H, d J = 2.8 Hz, CCHCHCNO2CH).

The synthetic route of 51605-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jackson, Alexander; Guilbert, Benedicte B.; Plant, Stuart D.; Goggi, Julian; Battle, Mark R.; Woodcraft, John L.; Gaeta, Alessandra; Jones, Clare L.; Bouvet, Denis R.; Jones, Paul A.; O’Shea, Dennis M.; Zheng, Penny Hao; Brown, Samantha L.; Ewan, Amanda L.; Trigg, William; Bioorganic and Medicinal Chemistry Letters; vol. 23; 3; (2013); p. 821 – 826;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 35203-44-2, 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 35203-44-2 as follows.

General procedure: A solution of N-alkylimidazole (10 mmol, 2 equivalents) and Dibromoalkane (5 mmol, 1 equivalent) was refluxed in toluene (20 mL) for 24?30 h. The reaction mixture was allowed to cool and toluene was decanted leaving a sticky solid behind. The sticky solid was washed three times with dry THF and finally with diethyl ether once. Solvent was removed under vacuum to get a white amorphous hygroscopic powder (88?94 percent yield). NMR spectra were recorded in D2O and/or DMSO-d6.

According to the analysis of related databases, 35203-44-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Aher, Sainath Babaji; Bhagat, Pundlik Rambhau; Research on Chemical Intermediates; vol. 42; 6; (2016); p. 5587 – 5596;,
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. 79917-88-7, name is 1,3-Dimethyl-1H-imidazol-3-ium chloride, A new synthetic method of this compound is introduced below., Quality Control of 1,3-Dimethyl-1H-imidazol-3-ium chloride

(1) Take 10g mass purity1,3-dimethyl-imidazolium chloride 25mL of distilled water was added to dissolve the solid, was added 55mL of 30percent concentration of hydrofluoric acid, stirred and heated to 50oC in the original closed;(2) reaction of starting material at least sufficient 3h, then heated to 100oC, excess hydrogen fluoride was evaporated and the product gas of hydrogen chloride gas, tail gas absorption using calcium oxide, not dehydrated to give 1,3-dimethyl-imidazol-fluorinated ionic liquids;(3) not to dehydrated 1,3-dimethylimidazolidinone fluorinated ionic liquid was diluted with distilled water was added, the volume is not dehydrated 1,3-dimethyl-fluorinated ionic liquid with distilled water, is less than 1:50, was added to the AgNO3 solution was diluted, if precipitation production, continue to add 20mL hydrofluoric acid, repeating (1) and (2) step until no precipitate was produced, purified non-dehydrated 1,3-dimethylimidazolidinone fluoride ionic liquids;(4) dewatering the non-purified non-dehydrated 1,3-dimethylimidazolidinone fluoride at 120oC ionic liquid was dried under high vacuum at least 48h, in addition to the depth of water, in addition to hydrogen fluoride, to give a viscous liquid of viscosity liquid detection, viscous liquid was added to distilled water, distilled water with viscous liquid volume ratio of less than 1:50, sealed and heated to 30oC, with hydrogen detector dilution residual amount of hydrogen fluoride, if the reading is greater than> 0.1ppm, continue to 120oC and dried under high vacuum in addition to fluorideHydrogen until the concentration of hydrogen fluoride test <0.1ppm; detecting if the hydrogen fluoride concentration <0.1ppm, the resultant liquid is 1,3-dimethylimidazolidinone fluorinated ionic liquids, weighing 8.52g. The synthetic route of 79917-88-7 has been constantly updated, and we look forward to future research findings. Reference:
Patent; Beijing University; Li, Zhongning; Zhong, Xiongwei; Xiong, Ting; Hu, Xianwei; Xu, Junli; Wang, Zhaowen; Gao, Bingliang; Yu, Jiangyu; (27 pag.)CN103992275; (2016); B;,
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

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

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

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

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

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