Month: May 2021

These common heterocyclic compound, 57667-50-2, name is 1-Propyl-1H-benzo[d]imidazol-2-amine, 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. Formula: C10H13N3

1 -Propyl- lH-benzimidazol-2-amine (0.600 g, 3.42 mmol), 3-({[(l,l- dimethylethyl)oxy]carbonyl}amino)benzoic acid (0.894 g, 3.77 mmol), EDC (0.722 g, 3.77 mmol), and EtaOAT (0.513 g, 3.77 mmol) were suspended in DMF (10 mL), followed by addition of NMM (0.414 mL, 3.77 mmol). After stirring at room temperature for 72 h, the contents were concentrated in vacuo and the crude product purified by reverse phase EtaPLC (used non-TFA containing mobile phase). The product was collected as a white solid (0.791 g, 59%). LC-MS (ES) m/z = 395.0 (M+Eta)+ 1H NMR (400 MHz, DMSOd6) delta ppm 12.71 (s, IH), 9.46 (s, IH), 8.36 (s, IH), 7.83 (d, J = 7.6 Hz, IH), 7.62 (d, J = 7.6 Hz, IH), 7.51-7.54 (m, 2H), 7.33-7.35 (m, IH), 7.21- 7.25 (m, 2H), 4.23 (t, J = 6.9 Hz, 2H), 1.92-1.95 (m, 2H), 1.50 (s, 9H), 0.94 (t, J = 7.3 Hz, 3H).

The synthetic route of 1-Propyl-1H-benzo[d]imidazol-2-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE LLC; LAFRANCE, Louis, Vincent; LEBER, Jack, Dale; LI, Mei; VERMA, Sharad, Kumar; WO2010/126922; (2010); 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. 15469-97-3, name is 1-Trityl-1H-imidazole, A new synthetic method of this compound is introduced below., SDS of cas: 15469-97-3

To a THF solution (80 mL) of 1-tritylimidazol (3.10 g), n-butyllithium (1.6M hexane solution, 6.9 ml) was added dropwise in an argon atmosphere with ice-cooling. After stirring at the same temperature for 30 minutes, (R)-2-[(benzyloxy)methyl]oxirane (1.52 mL) was added thereto. After stirring for 1.5 hours with ice-cooling and stirring at room temperature for 1 hour, water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with water and brine, dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by subjecting to silica gel chromatography (eluent; ethyl acetate:hexane = 1:1) to obtain the title compound (1.402 g) as a pale yellow oily product. 1H-NMR (CDCl3) delta: 2.06 (2H, dd, J = 2.8Hz, 18.0Hz), 3.08 (1H, dd, J = 5.4Hz, 9.8Hz), 3.21 (1H, dd, J = 5.4Hz, 9.8Hz), 3.55-3.7 (1H, m), 4.36 (2H, s), 6.73 (1H, d, J = 1.4Hz), 6.93 (1H, d, J = 1.4Hz), 7.0-7.4 (20H, m).

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; Takeda Chemical Industries, Ltd.; EP1350793; (2003); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 15813-07-7, The chemical industry reduces the impact on the environment during synthesis 15813-07-7, name is 5-Iodo-4-methyl-1H-imidazole, I believe this compound will play a more active role in future production and life.

Step B 1-Boc-4-iodo-5-methylimidazole A suspension of 4-iodo-5-methylimidazole (4.16 g, 20 mmol) and di-t-butyldicarbonate (5.24 g, 24 mmol) in methylene chloride (100 ml) containing triethylamine (4.0 ml, 28.7 mmol) was stirred at room temperature until homogeneity was achieved (2 h). The reaction mixture was then washed well with water, dried (Na2 SO4) and concentrated. The residue was chromatographed (5:1 hexane/ethyl acetate) to afford the title compound as a crystalline white solid. 1 H NMR (CDCl3) d 1.62 (s, 9 H), 2.43 (s, 3 H), 8.00 (s, 1 H).

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, 5-Iodo-4-methyl-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Merck & Co., Inc.; US5932606; (1999); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 288-32-4, 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. 288-32-4, name is 1H-Imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of Cu(OAc)2 (3.6 mg, 0.020 mmol), ligand II (21.6 mg, 0.020 mmol), and F-PEG (0.25 g, 0.10 mmol) in MeOH (1 mL) was heated to dissolve all the reagents added completely and MeOH was removed under the reduced pressure. H2O (6 mL) was added to the residue and then 4-methoxyphenylboroic acid (1a, 60.8 mg, 0.40 mmol) and imidazole (2a, 13.6 mg, 0.20 mmol) were added. The whole reaction mixture was stirred under an O2 atmosphere at room temperature for 24 h. The mixture was diluted with brine and extracted with AcOEt (30 mL×3). The organic layer was washed with H2O (10 mL×3) and dried over MgSO4. The solvent was removed under the reduced pressure and the residue was purified by SiO2 column chromatography using AcOEt to give N-(4-methoxyphenyl)imidazole (3aa) (26.4 mg, 78%).

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, 1H-Imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Inamoto, Kiyofumi; Nozawa, Kanako; Kadokawa, Jun; Kondo, Yoshinori; Tetrahedron; vol. 68; 38; (2012); p. 7794 – 7798;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 288-32-4, name is 1H-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 288-32-4, Application In Synthesis of 1H-Imidazole

General procedure: A THF solution of imidazole (1 equivalent) is added to a suspension of NaH (1.1 equivalents) (60 % in paraffin oil) previously stirred in n-hexane for 15 min. The imidazole solution is added dropwise over a period of 25-30 min at 5-10 C to avoid vigorous liberation of H2 gas. Once H2 gas evolution ceased, the suspension of imidazole sodium is stirred at RT for 2-3 h to favor complete formation of NaIm salt. To this suspension, corresponding R-Br (0.90 equivalents), was added dropwise over a period of 30 min and further stirred for 3 h or longer to achieve uniform mixing indicated by vertex formation. The thoroughly stirred reaction mixture then was refluxed overnight at 60-65 C. The reaction mass was then allowed to cool and filtered to remove NaBr salt. THF is removed under a rotary evaporator and DCM is added to the resultant brownish liquid followed by the addition of activated charcoal and anhydrous Na2SO4, stirred for 2-3 h and filtered over Celite. A Celite bed was washed with DCM and DCM removed under vacuum leading to a pale yellowish liquid. The NMR spectra checked in CDCl3 and matches with literature reports [20].

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:
Article; Aher, Sainath Babaji; Bhagat, Pundlik Rambhau; Research on Chemical Intermediates; vol. 42; 6; (2016); p. 5587 – 5596;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 614-97-1, 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. 614-97-1, name is 5-Methyl-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

5-methyl-i H-i ,3-benzodiazole (0.5 g, 7.6 mmol), Boc anhydride (2.44 g, ii .4 mmol), DMAP (92 mg, 0.76mmol) and triethylamine (2.11 mL, iSmmol) were dissolved in acetonitrile (10 mL). The mixture was stirred at 80C overnight, cooled and solvent was removed in vacuo. Crude product was purified via column chromatography using DCM as eluent. Fractions containing the title compound were combined and concentrated (0.80 g, 46%). UPLC (254nm): RT=3.75 mm, 93.2% purity, [M+H]=233.2.

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, 5-Methyl-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PROBIODRUG AG; HEISER, Ulrich; HOFFMANN, Torsten; LUES, Ingeborg; MEYER, Antje; (248 pag.)WO2018/178384; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 10111-08-7, name is Imidazole-2-carboxaldehyde, 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: 10111-08-7

To a solution of tert-butyl 2-bromoacetate (19.5 g, 100 mmol), 1H-imidazole-2-carbaldehyde (9.6 g, 100 mmol) in anhydrous DMF (50 mL) was added KI (4.98 g, 30 mmol) and DIPEA (26 mL, 150 mmol). The reaction mixture was stirred at 80 ?C under nitrogen for 5 h. After the solvent was evaporated under reduced pressure, the reaction mixture was diluted with DCM, washed with water and dried. Solvent was evaporated under reduce pressure to afford a residue, which was purified using a Biotage SP4 over silica gel and eluted with DCM to 6% methanol in DCM to 3a (17.30 g, 82%). 1H NMR (400 MHz, CDCl3) ? 9.78 (s, 1 H), 7.31 (s, 1 H), 7.12 (s, 1 H), 5.01 (s, 2 H), 1.46 (s, 9 H); MS (ESI), 211 (M+H)+.

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

Reference:
Article; Lu, Genliang; Maresca, Kevin P.; Hillier, Shawn M.; Zimmerman, Craig N.; Eckelman, William C.; Joyal, John L.; Babich, John W.; Bioorganic and Medicinal Chemistry Letters; vol. 23; 5; (2013); p. 1557 – 1563;,
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 570-22-9 as follows. name: 1H-Imidazole-4,5-dicarboxylic acid

General procedure: Ethane-1,2-diamine (4a; 60mg; 1mmol) and iminodiacetic acid (5; 266mg; 2mmol) were mixed thoroughly, grinded and subjected to focused microwave irradiation at 135 C for 4 minutes. TLC of reaction mixture over silica gel G using ethyl acetate: MeOH (7:3) as mobile phase showed that the reaction is complete. Crude product, so obtained was purified by crystallization from methanol: water (9.5:0.5) to give pure product 9a. Yield: 83%.

According to the analysis of related databases, 570-22-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kumar, Anuj; Banerjee, Somesh; Roy, Partha; Sondhi; Sharma, Anuj; Bioorganic and Medicinal Chemistry Letters; vol. 27; 3; (2017); p. 501 – 504;,
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. 4532-96-1, name is 1-Isopropyl-1H-imidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 1-Isopropyl-1H-imidazole

(a) 1-Isopropyl-2-(4-methoxybenzenesulphonyl) imidazole Into 20 ml of acetonitrile was introduced 0.1 mol of 1-isopropylimidazole. After that 0.1 mol of 4-methoxybenzenesulphonyl chloride in 20 ml of acetonitrile was added drop-by-drop. The addition took one hour and the temperature increased to 35 C. After one hour stirring at room-temperature 0.11 mol of triethylamine was added to the reaction medium and stirring was maintained for 20 hours. The precipitate which formed was suction-filtered the filtrate was evaporated to dryness and the residue was dissolved in ethyl acetate. After washing with neutral water, the extract was dried and isolated to give 18.3 g of a brownish oil which was purified on a silica column. The elution with ethyl acetate provided 4.5 g of a brownish oil which solidified. In this manner, 1-isopropyl-2-(4-methoxybenzenesulphonyl) imidazole was obtained in a yield of 16%. Purity: 99.9% (high pressure liquid chromatography) M.P.: 84-86 C. (ethyl acetate/n-hexane 1/2) Using the same procedure as that described above 1-benzyl-2-(4-methoxybenzenesulphonyl) imidazole was obtained in the form of a white beige solid. M.P.: 74.5 C. (ethyl acetate/n-hexane 1/2)

The synthetic route of 4532-96-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sanofi; US4994474; (1991); A;,
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. 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1003-21-0

5-Bromo-1-methyl-1H-imidazole (1.36 mL, 0.5 M in DCM over 3 A molecular sieves, 0.678 mmol) was treated with EtMgCl (0.325 mL, 2.09 M in THF, 0.678 mmol) dropwise under argon with stirring at room temperature over 1 minute, and the resulting translucent/semi-opaque reaction was stirred at room temperature for 20 minutes. This was treated dropwise over 2 minutes with a solution of 3-benzyl-6-(4-fluorobenzoyl)-N-methyl-4-(trifluoromethyl)quinoline-2-carboxamide (90.4 mg, 0.194 mmol, Intermediate 35: step f) in DCM (1.2 mL) with stirring at room temperature, and the resulting orange reaction was immediately stirred at 40 C. for 13 hours. The resulting orange opaque mixture was cooled to room temperature, partitioned with 5 M aqueous NH4Cl (3 mL), and the aqueous layer was extracted with DCM (1*5 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated. The residue was dry load flash chromatographed using 2:3 toluene/acetone (isocratic elution) to yield the title compound as a pale yellow foam. 1H NMR (400 MHz, CDCl3) delta ppm 8.32 (s, 1H), 7.88 (d, J=9.09 Hz, 1H), 7.69 (d, J=10.61 Hz, 1H), 7.30-7.38 (m, 3H), 7.10-7.24 (m, 4H), 6.97-7.09 (m, 4H), 6.29 (s, 1H), 4.91 (s, 2H), 3.39 (s, 3H), 2.89 (d, J=5.05 Hz, 3H); MS m/e 549.2 [M+H]+.

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 1003-21-0.

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.; Pierce, Joan; Goldberg, Steven; Fourie, Anne; Xue, Xiaohua; US2014/107094; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem