Month: February 2021

Synthetic Route of 33543-78-1, These common heterocyclic compound, 33543-78-1, name is Ethyl 1H-imidazole-2-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.

a solution of 9.5 g of ethyl imidazole-2-carboxylate, 9.9 g of 2,5-dibromo-1-indanone and 0.1 g of sodium iodide in 280 ml of ethanol is kept boiling for 16 hours, cooled to 20¡ã C. and dried under reduced pressure (20 mmHg; 2.6 kPa) at 50¡ã C. The product obtained (21 g) is dissolved in 50 ml of dichloromethane and the solution is washed 3 times with a total of 600 ml of distilled water, dried over anhydrous magnesium sulphate and dried under reduced pressure (20 mmHg; 2.6 kPa) at 50¡ã C. The product obtained (12.7 g) is chromatographed on 790 g of neutral silica gel (0.020-0.045 mm) contained in a column 7 cm in diameter, eluding under pressure with a dichloromethane-ethyl acetate mixture (70-30 by volume) and collecting 75-ml fractions. Fractions 70 to 140 are pooled and concentrated to dryness under reduced pressure (15 mmHg; 2 kPa) at 40¡ã C. 3.7 g of ethyl 1-(5-bromo-1-oxo-2-indanyl)imidazole-2-carboxylate are thus obtained which melt at 140¡ã C. The 2,5-dibromo-1-indanone can be prepared as described in European Patent 346107.

Statistics shows that Ethyl 1H-imidazole-2-carboxylate is playing an increasingly important role. we look forward to future research findings about 33543-78-1.

Reference:
Patent; Rhone-Poulenc Rorer S.A.; US5677306; (1997); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 45676-04-8,Some common heterocyclic compound, 45676-04-8, name is 1-tert-Butylimidazole, molecular formula is C7H12N2, 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.

This ligand was prepared according to a literature method [15] with slight modifications. A mixture of 2,6-dichloropyridine (1.5g, 10mmol) and 1-tert-butylimidazole (5.0g, 40mmol) was heated in an autoclave at 150C for 3 days. Upon cooling, the reaction mixture was dissolved in MeOH (5mL), followed by addition of a large amount of diethyl ether. After filtration, the precipitate was washed with acetone (20mL) and dried to give 2,6-bis(3-tert-butylimidazolium-1-yl)pyridine dichloride as an off-white solid (2.7g, 68%). 1H NMR (CD3CN): delta 10.37 (brs, 2H, NCHN), 8.97 (brs, 2H, imid), 8.58 (t, J=8.1Hz, 1H, 4-py), 8.46 (d, J=8.0Hz, 2H, 3,5-py), 8.36 (brs, 2H, imid), 1.72 (s, 18H, tBu). ESI-MS (m/z): 360.4 [M-Cl]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-tert-Butylimidazole, its application will become more common.

Reference:
Article; Nakamura, Takuo; Ogushi, Shinji; Arikawa, Yasuhiro; Umakoshi, Keisuke; Journal of Organometallic Chemistry; vol. 803; (2016); p. 67 – 72;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 1008361-65-6, name is 5-Bromo-6-methoxy-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 1008361-65-6, Product Details of 1008361-65-6

Compound 5-bromo-6-methoxy-1H-benzimidazole 60d (430.0 mg, 1.9 mmol), triethylamine (383.0 mg,3.8 mmol) and 4-dimethylaminopyridine (23.0 mg, 0.2 mmol)With tetrahydrofuran (15.0 mL)After mixing, di-tert-butyl dicarbonate (585.0 mg, 2.9 mmol) was added at room temperature, and the reaction was carried out at 45 C for 12 hours.The reaction solution was diluted with methylene chloride (100 mL) and washed with brine. The organic phase is dried over anhydrous sodium sulfate and filtered to dissolve to give a mixture of 1-t-butoxy acyl-5-Bromo-6-methoxy-benzimidazole 60e and 3-tert-butoxycarbonyl-5-bromo-6-methoxy-benzimidazole 61e (450.0 mg,1.4 mmol, white solid), yield 73%.

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-Bromo-6-methoxy-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nanjing Tianyinjianhua Pharmaceutical Technology Co., Ltd.; Kong Xianglong; Zhou Chao; Zheng Zhixiang; (105 pag.)CN109020957; (2018); A;,
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. 256519-11-6, name is 2-Chloro-7-fluoro-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., Formula: C7H4ClFN2

A mixture of 2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5- (piperidin-3-yl)benzofuran-3-carboxamide (80 mg, 0.174 mmol), 2-chloro-4-fluoro-1H-benzo[d]imidazole (47.5 mg, 0.279 mmol) and triethylamine (90 mg, 0.696 mmol) in DMF (1 ml)was heated to 170C for 40 mm. The reaction mixture was cooled to RT and partitioned between EtOAc and water. The organic layer was dried in Na2SO4 and concentrated under vacuum. Then the reaction mixture separated by SFC on a ChiralPark AD, 3×25 cm, 40% MeOH(0.1%NH3.H20)/C02 to afford Example 55 (Enantiomer 1, peak 1 on SFC, HPLC_RT=3.91mm) as white solid 5 mg (10%) (LC-MS (ES, mlz) C30H29F2N5045: 593; Found: 594 [M+H]b) and Example 56 (Enantiomer 2, peak 2 on SFC, HPLC_RT=6.34 mm) as white solid 5 mg (10%) (LCMS (ES, mlz) C30H29F2N504S: 593; Found: 594 [M+Hf).

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; MERCK SHARP & DOHME CORP.; HE, Shuwen; LAI, Zhong; DAI, Xing; XIAO, Dong; LONDON, Clare; ZORN, Nicolas; NARGUND, Ravi; PALANI, Anandan; MCCOMAS, Casey C.; LI, Peng; PENG, Xuanjia; SOLL, Richard; WO2014/205592; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 616-47-7, A common heterocyclic compound, 616-47-7, name is 1-Methyl-1H-imidazole, molecular formula is C4H6N2, 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: The ionic liquids used in this study (Fig. 1) were synthesized as described in the literature [23,24]. IL-1, for example, was prepared as follows: 1-methylimidazole (16.4g, 0.2mol) and 1, 4-butanesultone (27.28g, 0.2mol) were mixed in a 100mL round bottom flask. The mixture was stirred at 42-45C for 17h. The white solid zwitterion was washed repeatedly with ether to remove non-ionic residues, filtrated through a Buchner funnel, and dried in vacuum for 4h. A stoichiometric amount of trifluoroacetic acid (22.8g, 0.2mol) was added dropwise, and the mixture was stirred for 6h at 80C. The viscous liquid was washed three times with ether and dried in vacuum to form IL-1.

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; Tao, Fu-Rong; Zhuang, Chen; Cui, Yue-Zhi; Xu, Jing; Chinese Chemical Letters; vol. 25; 5; (2014); p. 757 – 761;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route 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.

EXAMPLE 1; [4-(1-{3-[2-(3-phenylsulphonylamino-phenyl)-2-hydroxy-ethylamino]-3-methyl-butyl}-1H-imidazol-4-yl)-phenyl]-acetic acid-hydrotrifluoroacetate; a. Tert-butyl [3-(4-iodo-imidazol-1-yl)-1,1-dimethyl-propyl]-carbamate; 3.88 g (20 mmol) 4-iodoimidazole are dissolved in 30 ml DMPU and at 5 C., 556 mg (22 mmol) 95% sodium hydride are added batchwise. After the development of gas has died down the reaction mixture is stirred for 1 hour at 10 C. Then a solution of 4.44 g (20 mmol) tert-butyl (3-chloro-1,1-dimethyl-propyl)-carbamate in 5 ml DMPU and 739 mg (2.0 mmol) tetrabutylammonium iodide are added. The reaction mixture is stirred for 16 hours at ambient temperature and then heated to 80 C. for 24 hours. After cooling to ambient temperature the reaction solution is poured onto a mixture of 500 ml ice water and 250 ml of ethyl acetate. The aqueous phase is separated off and extracted with ethyl acetate. The combined organic phases are washed with water and saturated aqueous sodium chloride solution, dried on sodium sulphate and evaporated down using the rotary evaporator. The residue is chromatographed on silica gel (petroleum ether/ethyl acetate=80:20?0:100).Yield: 1.66 g (22% of theory)C13H22IN3O2 (379.24)Mass spectrum: (M+H)+=380Rf value: 0.45 (silica gel; petroleum ether/ethyl acetate=1:1)

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

Reference:
Patent; Walter, Rainer; Trieselmann, Thomas; Netherton, Matthew R.; Santagostino, Marco; Hamilton, Bradford S.; US2008/300290; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 24155-42-8, A common heterocyclic compound, 24155-42-8, name is 1-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol, molecular formula is C11H10Cl2N2O, 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.

EXAMPLE 5 2-[[1-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy]methyl]quinoline, hydrochloride (1:2) 3.2 g of 2-Chloromethylquinoline hydrochloride (0.015 mol) (commercially available), 3.85 g of 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol (0.015 mol), 14.8 g sodium hydroxide (0.37 mol) in 25 ml of water, 0.25 g of benzyltrimethylammonium chloride and 40 ml of tetrahydrofuran are reacted in a manner as described in Example 1. After work up, the oily product (6.4 g) is dissolved in 150 ml of ether, charcoaled and then etheral hydrochloric acid is added to the clear solution while stirring. The precipitated hydrochloride (5.8 g) is filtered off, washed with ether and hexane and recrystallized from acetonitrile; m.p. 148-149 C. The following additional products of formula D or E are obtained by the procedure of Example 1 by reacting the unsubstituted or substituted 1-phenyl-2-(1H-imidazol-1-yl)ethanol of formula A with the unsubstituted or substituted 2-chloromethylquinoline of formula B or the unsubstituted or substituted 4-chloromethylquinoline of formula C. The substituents apply to the respective formulae.

The synthetic route of 24155-42-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; E. R. Squibb & Sons, Inc.; US4282230; (1981); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 33543-78-1, name is Ethyl 1H-imidazole-2-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 33543-78-1, SDS of cas: 33543-78-1

PREPARATION 32 1H-imidazole-2-carboxylic acid 21.75 mL (43.5 mmol) of a 2M solution of lithium hydroxide in water were added to a solution of 1.22 g (8.71 mmol) of ethyl 1H-imidazole-2-carboxylate (ref) in a mixture of tetrahydrofurane (20 mL) and water (20 mL). The reaction mixture was warmed up to reflux, and stirred for 1.5 hours. The reaction mixture was cooled to room temperature and the solvent was evaporated under vacuum. The crude residue (3.0 g) was used in next step without further purification. LRMS (m/z): 113 (M+1)+.

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; Almirall, S.A.; EP2518070; (2012); 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. 29914-81-6, name is 1,3-Bis(1H-benzo[d]imidazol-2-yl)benzene, A new synthetic method of this compound is introduced below., Formula: C20H14N4

General procedure: To 10 mL dry acetone were added [Ru(H2bip)Cl3] (54 mg,0.10 mmol) and AgOTf (96 mg, 0.37 mmol). The mixture wasrefluxed for 2 h before cooling to room temperature. The resultingAgCl precipitate was removed by filtration, and the filtrate wasconcentrated to dryness. To the residue were added ligand Mebib(36.9 mg, 0.11 mmol), DMF (10 mL), and t-BuOH (10 mL). Themixture was then refluxed for 24 h. After cooling to room temperature,the solventwas removed under reduced pressure, and theresiduewas dissolved in a mixture of 10 mL methanol and 1mL 1Maq. HCl. The mixture was then treated with 100 mg KPF6. Theresulting precipitate was collected by filtration and washing withwater and Et2O. The obtained solid was subjected to flash columnchromatography on silica gel (eluent: CH3CN/H2O/aq.KNO3, 100/10/0.2) to give 34.5 mg of 1(PF6)2 in 37% yield.

The synthetic route of 29914-81-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shao, Jiang-Yang; Zhong, Yu-Wu; Journal of Organometallic Chemistry; vol. 845; (2017); p. 144 – 150;,
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. 3012-80-4, name is 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Formula: C9H8N2O

To a 0¡ãC solution of 1 -methyl- lH-benzimidazole-2-carbaldehyde (1.1 g, 6.8 mmol) in anhydrous methanol (50 mL) was added sodium borohydride (350 mg, 9.3 mmol). The reaction mixture was stirred at room temperature for 5 hours. Saturated ammonium chloride solution (20 mL) was added. Methanol was evaporated. The resultant mixture was extracted with EtOAc (3 x 50 mL) and CH2Cl2 (1 x 50 mL). The organic extracts were combined, dried over MgSO4, filtered, evaporated, and dried in vacuo. (1 -methyl- lH-benzimidazol-2-yl)methanol was obtained (1.1 g, 99percent yield). The product was used without further purification.

The synthetic route of 3012-80-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHLORION PHARMA, INC.; UNIVERSITE LAVAL; ATTARDO, Giorgio; TRIPATHY, Sasmita; WO2010/132999; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem