Month: August 2021

Adding a certain compound to certain chemical reactions, such as: 66121-69-5, name is 1-Methyl-1H-imidazole-4-carbonitrile, 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 66121-69-5, Product Details of 66121-69-5

43.4 ml 1 .4M methylmagnesiumbromide in toluene were added dropwise to a mixture of 5.0 g 1 -methyl-1 H-imidazole-carbonitrile in 70 ml diethylether at 0C. After 30 min , the mixture was warmed up to ambient temperature. After 1 h the reaction was quenched with 1 M aqueous HCI solution and neutralised with saturated sodium bicarbonate solution. The reaction mixture was extracted with dichloromethane. The combined organic extracts were dried with magnesium sulfate and concentrated under reduced pressure. The crude material was purified by flash chromatography (dichloromethane/methanol = 98/2) to give the intermediate 3.3. Yield: 4.8 g of 3.3 (75% content; 62% of theory); Analysis: [M+H]+ = 125

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; DAHMANN, Georg; DOLLINGER, Horst; GNAMM, Christian; FIEGEN, Dennis; HOFFMANN, Matthias; LAMB, David, James; KLICIC, Jasna; SCHNAPP, Andreas; WO2013/156608; (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. 3314-30-5, name is 1H-Benzo[d]imidazole-2-carbaldehyde, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H6N2O

General procedure: A flask was equipped with a magnetic stir bar and charged with 1Hpyrrole-2-carbaldehyde (2a; 19.0 mg, 0.2 mmol, 1.0 equiv), 2-bromophenylacetonitrile(1a; 39.2 mg, 0.2 mmol, 1.0 equiv), and K3PO4(63.6 mg, 0.3 mmol, 1.5 equiv). The flask was evacuated and filledwith N2, and then anhydrous DMSO (2.0 mL) was introduced via a syringe.The flask was heated in a 130 °C oil bath for 24 h, at which timeTLC analysis [petroleum ether (bp 60?90 °C)?EtOAc, 10:1] indicatedcomplete consumption of 2a and 1a. The reaction mixture was cooledto r.t. and added to a sat. solution of NaCl (20 mL) and extracted withEtOAc (3 × 10 mL). The combined organic layers were dried (Na2SO4)and filtered. The filtrate was concentrated, and the residue was purified by column chromatography on SiO2 [petroleum ether (bp 60?90°C)?EtOAc, 10:1 to 30:1] to give 3ai; Yield: 19.9 mg (41percent); tan solid; mp 251.7?252.8 °C.

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; Jiang, Zeng-Qiang; Miao, Da-Zhuang; Tong, Yao; Pan, Qiang; Li, Xiao-Tong; Hu, Ren-He; Han, Shi-Qing; Synthesis; vol. 47; 13; (2015); p. 1913 – 1921;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 54624-57-6,Some common heterocyclic compound, 54624-57-6, name is 2-Bromobenzimidazole, molecular formula is C7H5BrN2, 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.

Among them, “·” represents a boron hydrogen bond B-H. n-BuLi (1.6M) in n-hexane solution (1.00mL, 1.6mmol) was slowly added dropwise to the ortho-carboborane-o-C2B10H10 at -78 C(92.0 mg, 0.64 mmol) in tetrahydrofuran solution, stirring at this temperature for 30 minutes,After slowly increasing to room temperature, the reaction was continued for 1 hour and then bromobenzimidazole was added.(126.7 mg, 0.64 mmol), continued to react at room temperature for 6 hours. Then, the binuclear ruthenium compound [Cp*RhCl2] 2 (256.0 mg, 0.32 mmol) was added to the reaction system for further reaction for 3 hours.After completion of the reaction, the mixture was allowed to stand for filtration, and the solvent was evaporated to dryness, and the obtained crude product was subjected to column chromatography (petrole ether / THF / 6:1) to give a red target product (III).Complex Rh (265.6 mg, yield 78%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromobenzimidazole, its application will become more common.

Reference:
Patent; Shanghai Institute of Technology; Yao Zijian; Fan Xiaonan; Gao Yonghong; Deng Wei; (9 pag.)CN110117299; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference 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.

Anhydrous THF (25 mL) was cooled in an ice bath. After NaH (1.40 g, 35 mmol, 60%) was added to the THF in one portion, the mixture was stirred at rt for 30 min and cooled in an ice bath. Then a solution of 1H-imidazole (2.00 g, 30 mmol) in anhydrous THF (6 mL) was added dropwise. The reaction mixture was then warmed to rt and stirred at rt for 1.5 h. To the mixture was added 1-bromo-3-chloropropane (4.60 g, 30 mmol) dropwise, and stirred at rt overnight. To the resulting mixture was added MeOH (5 mL) in one portion. The resulting mixtue was filtered and the filtrate was concertrated in vacuo. The residue was purified by a silica gel column chromatography (DCM/MeOH (V/V)=30:1) to give the title compound as pale yellow oil (3.10 g, 73%).

Statistics shows that 1H-Imidazole is playing an increasingly important role. we look forward to future research findings about 288-32-4.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; Zhang, Yingjun; Zhang, Jiancun; Wang, Xiaojun; Lin, Runfeng; Cao, Shengtian; Wang, Zhaohe; Li, Jing; US2015/87639; (2015); A1;,
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. 28890-99-5, name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C13H9N3

The intermediate materials of Pt(ppy)ppyHCl and Pt(ppy)2C12 may be prepared using a previously reported procedure (Inorg. Chem. 2010, 49, 11297-11308, which is incorporated by reference herein in its entirety). Briefly, a mixture of 2-phenylpyridine and potassium tetrachloroplatinate in tert-butanol and water is heated to reflux to provide Pt(ppy)ppyHCl, which is then reacted with 5H-benzo[d] benzo[4,5]imidazo[1 ,2-a]imidazole in the presence of potassium carbonate in dichloromethane at reflux to provide Compound 301.

According to the analysis of related databases, 28890-99-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Universal Display Corporation; Chen, Hsiao-Fan; Silverstein, Daniel W.; Brooks, Jason; Feldman, Jerald; (143 pag.)US2018/331306; (2018); 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. 10040-98-9, name is 4-Imidazol-1-yl-benzaldehyde, A new synthetic method of this compound is introduced below., Formula: C10H8N2O

A mixture of 4-(1H-imidazol-1-yl)benzaldehyde (0.025mol) and thiosemicarbazide (0.025 mol) in ethanol (40 mL)was refluxed for 12 h. The reaction mixture was cooled andfiltered. The product was crystallized from ethanol.M.p. 250.1 C.IR numax (cm-1): 3352.28 (N-H stretching), 3113.11 (AromaticC-H stretching), 2981.95 (Aliphatic C-H stretching), 1633.71,1608.63, 1533.41, 1517.98, 1473.62 (C=N, C=C stretchingand N-H bending), 1359.82 (C-H bending), 1300.02,1236.37, 1180.44, 1089.78, 1060.85 (C-N, C=S stretchingand aromatic C-H in plane bending), 960.55, 939.33, 914.26,835.18, 812.03, 767.67, 632.65, 617.22 (Aromatic C-H outof plane bending).1H NMR (400 MHz, DMSO-d6) delta (ppm): 7.11 (s, 1H),7.69 (d, J= 8.8 Hz, 2H), 7.82 (s, 1H), 7.93 (d, J= 8.4 Hz,2H), 8.05 (s, 1H), 8.09 (s, 1H), 8.24 (s, 1H), 8.34 (s, 1H,CH=N), 11.49 (s, 1H).MS (ESI) (m/z): (M+H)+ 246Anal. Calcd for C11H11N5S: C, 53.86; H, 4.52; N, 28.55.Found: C, 53.85; H, 4.54; N, 28.52.

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; Ciftci, Guel?en Akalin; Altintop, Mehlika Dilek; Temel, Halide Edip; Oezdemir, Ahmet; Kaplancikli, Zafer Asim; Letters in drug design and discovery; vol. 14; 5; (2017); p. 554 – 566;,
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 21252-69-7 as follows. Recommanded Product: 21252-69-7

General procedure: To a screw capped tube flask,chloroalkylated quaternary ammonium salt 2 and 5 equivalents of alkyl imidazole 3 were added with acetonitrile (5 ml). The sealed flask was heated at 100 for 24h. After the solvent was removed by evaporation, the residue was dissolved in a small amount of dichloromethane. The solution was poured into ethyl acetate, anoily imidazolium salt was separated from an organic phase. In case of 4ao, it was recrystallized in ethylacetate. Salt 4 was also moisture-sensitive as 2.

According to the analysis of related databases, 21252-69-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Cho, Beom Shin; Jung, Il Gu; Chung, Young Keun; Han, Jin Wook; Bulletin of the Korean Chemical Society; vol. 36; 2; (2015); p. 451 – 452;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 53484-18-7, name is 1-Methyl-1H-benzo[d]imidazole-6-carboxylic acid, 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 53484-18-7, Computed Properties of C9H8N2O2

Oxalyl chloride (42 mu, 0.47 mmol, 1.7 eq) was added dropwise to a mixture of 1- methyl-lH-benzo[d]imidazole-6-carboxylic acid (50 mg, 0.28 mmol, 1.0 eq) and DMF (2 mu, 0.03 mmol, 0.1 eq) in DCM (0.8 mL). The reaction was stirred at rt for 2 hrs. The reaction was concentrated under reduced pressure to give crude l-methyl-lH-benzo[d]imidazole-6- carbonyl chloride as a yellow residue that was used without further purification.

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

Reference:
Patent; ENANTA PHARMACEUTICALS INC; GRANGER, Brett; WANG, Gouqiang; SHEN, Ruichao; MA, Jun; XING, Xuechao; HE, Jing; HE, Yong; LONG, Jiang; WANG, Bin; OR, Yat, Sun; (108 pag.)WO2018/218044; (2018); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 137049-00-4, These common heterocyclic compound, 137049-00-4, name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, 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 15(6-{[4-(1-Butylcyclopropyl)benzyl](1-methyl-1H-imidazol-4-ylsulfonyl)aminomethyl}pyridin-2-ylamino)acetic acid (Exemplary compound No. 1138)15-(a): tert-Butyl [tert-butoxycarbonyl(6-{[4-(1-butylcyclopropyl)benzyl](1-methyl-1H-imidazol-4-ylsulfonyl)aminomethyl}pyridin-2-yl)amino]acetateTo 6 ml of a methylene chloride solution containing 307 mg (0.586 mmol) of tert-butyl [tert-butoxycarbonyl(6-{[4-(1-butylcyclopropyl)benzyl]aminomethyl}pyridin-2-yl)amino]acetate obtained in Reference example 13 were added uncer ice-cooling 163 mul (1.17 mmol) of triethylamine and 127 mg (0.703 mmol) of 1-methyl-1H-imidazol-4-ylsulfonyl chloride, and the mixture was stirred at the same temperature for 2.5 hours and at room temperature for 6 hours. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with methylene chloride. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was applied to silica gel column chromatography (eluent; n-hexane:ethyl acetate=3:7?1:3 (V/V)), and the fractions containing the objective material were concentrated under reduced pressure to obtain 293 mg of the title compound as colorless oily product. (Yield: 75%)Mass Spectrum (CI, m/z): 668 (M++1).1H-NMR Spectrum (CDCl3, delta ppm): 7.65 (d, J=8.2 Hz, 1H), 7.46 (dd, J=8.2, 7.4 Hz, 1H), 7.38 (d, J=1.2 Hz, 1H), 7.18 (d, J=1.2 Hz, 1H), 7.15 (s, 4H), 6.96 (d, J=7.4 Hz, 1H), 4.58 (s, 2H), 4.50 (s, 2H), 4.38 (s, 2H), 3.67 (s, 3H), 1.55-1.47 (m, 2H), 1.52 (s, 9H), 1.43 (s, 9H), 1.26-1.15 (m, 4H), 0.83 (t, J=6.8 Hz, 3H), 0.74-0.68 (m, 2H), 0.66-0.59 (m, 2H).

The synthetic route of 137049-00-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UBE INDUSTRIES, LTD.; US2012/259123; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 96797-15-8, name is 4-Iodo-1-trityl-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. Product Details of 96797-15-8

Compound 1 (2.2 g, 5.0mmol), o-formylphenylboronic acid(1.2 g, 7.5mmol), K3PO4 (3.2 g, 15mmol), Pd (PPh3)4 (0.6 g, 1.0mmol) is dissolved in DMF/H20 (30mL/6mL). The system is replaced with nitrogen and warmed at 90C, the reaction is stirred overnight. The reaction solution is diluted with ethyl acetate (50mL), wash with saturated brine (25mL X 3), dry over anhydrous sodium sulfate, and dry under reduced pressure. Crude column chromatography (PE: EA = 5:1), and then obtained brown solid compound 2 (810 mg, 39%).

The synthetic route of 4-Iodo-1-trityl-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Lunan Pharmaceutical Group Co., Ltd.; Zhang Guimin; Guan Yongxia; Li Xin; (15 pag.)CN107556315; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem