Month: September 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. 496-46-8, name is Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, A new synthetic method of this compound is introduced below., Application In Synthesis of Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

After melting glycouryl (5.7 g, 40mmol) in 20 ml_ of sulfuric acid (9M), an aqueou s formaldehyde solution (7.0 mL, 91 mmol) was added. The resultant reaction mixture was stirred at 75 0C for 24 hours. The temperature was raised to 95-1000C, and the r eaction was further performed. 200 mL of water was quickly poured into the reaction mixture, and 1L of acetone was further added to obtain a precipitate. The precipitate was filtered under reduced pressure and washed with a 1 :4 mixed solution of water and acetone. The solid filtrate was dissolved in 200 mL of a 1 :1 mixed solution of water a nd acetone and filtered under reduced pressure to remove a precipitate (cucurbit[6]uril). 800 mL of acetone was added to the filtrate to precipitate a mixture of cucurbit[7 ]uril and cucurbit[5]uril. The precipitated mixture of cucurbit[7]uril and cucurbit[5]uril wa s dissolved in 40 mL of water, and 25 mL of methanol was added to precipitate only cue urbit[7]uril. The precipitated cucurbit[7]uril was filtered under reduced pressure and dri ed in a vacuum. The results of an analysis are as follows.1H NMR (500 MHz, D2O): delta = 5.56 (d, 14H), 5.35 (s, 14H), 4.11 (d, 14H).

The synthetic route of 496-46-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; POSTECH ACADEMY-INDUSTRY FOUNDATION; WO2007/46575; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 53710-78-4, The chemical industry reduces the impact on the environment during synthesis 53710-78-4, name is 1-(3-Chloropropyl)-1H-imidazole, I believe this compound will play a more active role in future production and life.

General procedure: To a solution of 24 (53 mg, 0.1 mmol) in DMF (25 mL), 60% NaH (4.2 mg, 0.105 mmol) was added portionwise at room temperature. After stirring for 30 min, alkyl halide (0.15 mmol) was added and the mixture was then reacted at 80 C for 10h. After cooling, the mixture was poured into water (100 mL) and extracted with ethyl acetate (3×50mL). The organic phase was combined, washed with brine (3×100mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using dichloromethane/methanol/triethylamine (120:4:1, v/v/v) as eluent to afford 28d and 28e.

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-(3-Chloropropyl)-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Ye, Qing; Shen, Yanhong; Zhou, Yubo; Lv, Dan; Gao, Jianrong; Li, Jia; Hu, Yongzhou; European Journal of Medicinal Chemistry; vol. 68; (2013); p. 361 – 371;,
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 6775-40-2 as follows. category: imidazoles-derivatives

2-amino-4-phenyl-1H-imidazole and 1-iodopropane are dissolved in absolute ethanol,Reaction at 80 and catalytic system for 20h, cooling to 50 ,1-propyl-4-phenyl-1H-imidazol-2-amine is prepared, in which the catalytic system consists of cuprous iodide,8-hydroxyquinoline and K3PO4,The molar ratio of 2-amino-4-phenyl-1H-imidazole to 1-iodopropane is 1: 1.5.The molar ratio of cuprous iodide to 8-hydroxyquinoline is 1: 1.7.The molar ratio of cuprous iodide to 2-amino-4-phenyl-1H-imidazole is 0.15: 1,The molar ratio of K3PO4 to 2-amino-4-phenyl-1H-imidazole is 2.4: 1;

According to the analysis of related databases, 6775-40-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Donghua University; Cai Zhengguo; Li Yanqing; Xiao Ru; (35 pag.)CN110396116; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1450-93-7,Some common heterocyclic compound, 1450-93-7, name is 1H-imidazol-2-amine sulfate(2:1), molecular formula is C6H12N6O4S, 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 13 7-Methyl-5-[3-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine A mixture of 5.14 g of (3-dimethylamino)-1[3-(trifluoromethyl)phenyl]-2-butene-1-one, 1.64 g of anhydrous sodium acetate and 2.64 g of 2-aminoimidazole hemisulfate in 100 ml of glacial acetic acid was refluxed for six hours. The solvent was removed in vacuo and the solid residue was partitioned between a saturated aqueous sodium bicarbonate solution and dichloromethane. The organic layer was separated and dried over powdered anhydrous sodium sulfate, then passed through a short column of a hydrous magnesium silicate. The effluent was refluxed on a steam bath with the gradual addition of hexane until crystallization was noted. On cooling the product was separated and collected by filtration and gave 2.55 g of the desired compound as off-white crystals, m.p. 170-172 C.

The synthetic route of 1450-93-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Cyanamid Company; US5037980; (1991); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 934-22-5, The chemical industry reduces the impact on the environment during synthesis 934-22-5, name is 6-Aminobenzimidazole, I believe this compound will play a more active role in future production and life.

Example 12; 1-(6-([(1S)-1-phenylethyl]amino/pyrazin-2-yl)-1H-benzimidazol-5-amine and 1-(6-([(1S)-1-phenylethyl]amino/pyrazin-2-yl)-1H-benzimidazol-6-amine To a stirred solution of 5-amino-benzimidazole (290mg, 2.2mmol) in anhydrous DMF (lOmL) under Ni was added caesium carbonate (980mg) The resulting mixture was stirred at 70’C for 60 min. To this was added a solution of 6-chloro-N- [ (lS)-l- phenylethyllpyrazin-2-amine (470mg) in DMF (5mL) and the resulting mixture was then heated at reflux for 48h. The DMF was removed under reduced pressure and the residue diluted with chloroform.. The organic layer was washed with aqueous Na2CO3, dried (Na2SO4) and the solvent removed under reduced pressure to furnish the crude product. Column chrumatography using dichloromethane-methanol (95 : 5-92 : 8) as eluant separated two fractions from unreacted starting material. The higher Rf fraction was assigned as the 6-isomer (276mg, 42%). 1H-n.m.r. (CDCl3) No.1. 64 (d, 3H, J=6.9Hz, CH3), 2. 90 (br s, 2H, NH2), 5. 05 (m, 1H, CH), 5.21 (d, 1H, NH), 6.70 (dd, 1H, J=8. 7, 2. 1Hz, benzimid-H), 6. 97 (d, 1H, = l. 8Hz, benzimid-H), 7. 28-7. 43 (m, 5H, Ph-H), 7. 58 (d, 1H, J= 8. 4Hz, benzimid-H), 7. 84 (s, IH, pyraz-H), 8.08 (s, 1 pyraz-H), 8. 21 (s, 1H, benzimid-H). m/z (ES) 331 (M++H). The lower fraction was assigned aa the 5-isomer (170mg, 26%)

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, 6-Aminobenzimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CYTOPIA RESEARCH PTY LTD; WO2005/66156; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 104619-51-4, 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. 104619-51-4 name is Di(1H-imidazol-1-yl)methanimine, 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.

To a solution of 5-(methylamino)-2-nitrophenol (KR-100001) (6.72 mmol, 1.13 g) in methanol (125 mL), PtO2 (0.34 mmol, 0.08 g) was added. The reaction was flushed with argon followed by hydrogen for fifteen minutes each with constant magnetic stirring. The reaction was then maintained under hydrogen atmosphere at ordinary pressure (balloon) for fifteen hours. Argon was again flushed through the reaction vessel for 15 minutes. Then the reaction contents were filtered quickly over a thin pad of celite which was then immediately washed with methanol (40 mL). The filtrate was concentrated in vacuo yielding an intense purple residue. The residue was quickly re-dissolved in acetonitrile (60 mL) and di(imidazole-1-yl)methanimine (16.81 mmol, 2.71 g) was added with constant magnetic stirring. The reaction was then placed under argon atmosphere and refluxed for six hours. The reaction was concentrated under reduced pressure and silica gel column chromatography (2:1 hexanes/ethyl acetate) provideded a crystalline white solid in a 41% yield. The product of the reduction (2-amino-5-(methylamino)phenol) is air unstable and appropriate measures should be taken to minimize air exposure.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Di(1H-imidazol-1-yl)methanimine, and friends who are interested can also refer to it.

Reference:
Article; Rynearson, Kevin D.; Charrette, Brian; Gabriel, Christopher; Moreno, Jesus; Boerneke, Mark A.; Dibrov, Sergey M.; Hermann, Thomas; Bioorganic and Medicinal Chemistry Letters; vol. 24; 15; (2014); p. 3521 – 3525;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 75370-65-9, name is 4-Amino-1H-benzo[d]imidazol-2(3H)-one, 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 75370-65-9, Application In Synthesis of 4-Amino-1H-benzo[d]imidazol-2(3H)-one

Preparation of 1-(4-fluorobenzyl)-3-(2,3-dihydro-2-oxo-1H-benzo[d]imidazol-4-yl)urea Commercially available p-fluorobenzylamine (0.76 ml, 6.7 mmol) was dissolved in 40 ml of AcOEt and at 0C triphosgene (1.98 g, lequiv.) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 20 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound 1a (900 mg, 6 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt). The solvent was evaporated and the crude was dissolved in AcOEt (50 ml) and washed with water (1 X 30 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 420 mg of a white solid. Yield = 23% 1HNMR (DMSO, 200 MHz) delta 4.29 (2H, d, J = 6 Hz), 6.62 (1H, dd, J = 7.6Hz, J’ = 1.2 Hz), 6.80 (2H, m), 6.95 (1H, dd, J = 8.2 Hz, J’ = 1.2 Hz), 7.15 (2H, m), 7.35 (2H, m), 8.23 (1H, bs), 9.96 (1H, bs), 10.59 (1H, bs); [M+1] 301.1 (C15H13FN4O2 requires 300.29).

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, 4-Amino-1H-benzo[d]imidazol-2(3H)-one, other downstream synthetic routes, hurry up and to see.

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

Adding a certain compound to certain chemical reactions, such as: 16681-56-4, name is 2-Bromo-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 16681-56-4, Quality Control of 2-Bromo-1H-imidazole

In a 10 mL vial was added N-(2,4-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4-(pyridin-2-ylmethoxy)benzamide (0.25 g, 0.55 mmol), 2-bromo-1H-imidazole (0.12 g, 0.82 mmol), and Cs2CO3 (0.44 g, 1.36 mmol) in dioxane (5 mL) to give a brown suspension. The reaction mixture was diluted with water (2 mL). Nitrogen was bubbled in for 20 min before Pd(PPh3)4 (0.063 g, 0.05 mmol) was added. The reaction was heated at 110 C for 4 h under microwave conditions. The reaction mixture was concentrated under reduced pressure. The residue was purified by Gilson HPLC (MeCN/0.1% TFA in water). To the purified product was added HCl in Et2O (0.5 mL, 1 mmol). The mixture was concentrated in vacuo to give the HCl salt of the title compound (10 mg, 4.2%). 1H NMR (DMSO-d6) ? 2.31 (s, 3H), 2.36 (s, 3H), 5.32 (s, 2H), 7.18 (d, 2H), 7.39(s, 1H), 7.45 (br s, 1H), 7.61 (s,2H), 7.84 (s, 2H), 7.96 (m, 3H), 8.63 (d,1H), 9.90 (s, 1H), 14.54 (br s, 1H); MS (M+H+) = 399.

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, 2-Bromo-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Yang, Bin; Hird, Alexander W.; Bodnarchuk, Michael S.; Zheng, Xiaolan; Dakin, Les; Su, Qibin; Daly, Kevin; Godin, Robert; Hattersley, Maureen M.; Brassil, Patrick; Redmond, Sean; John Russell, Daniel; Janetka, James W.; Bioorganic and Medicinal Chemistry; vol. 28; 2; (2020);,
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. 4887-80-3, name is 5-Methoxy-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H8N2O

5-methoxybenzimidazole (0.296 g, 2 mmol), 2-(4-Diethylamino-2-hydroxy) benzoylbenzoic acid (0.626 g, 2 mmol) were mixed and addedinto concentrated H2SO4 (3 mL), heated at 100 C for 6 h, and thenslowly cooling to ambient temperature. The resulting mixture wasslowly poured into ice cold water, neutralized by saturated aqueousNaHCO3 followed by extraction with CH2Cl2 (50 mL×3). The organiclayers were collected and dried over Na2SO4, which was subsequentlyevaporated to remove CH2Cl2. Finally, target compound BiF was obtainedas a white powder in yield of 82.0% (0.768 g) through columnchromatography over silica gel eluting with CH2Cl2/CH3OH (v/v=20 :1). M.p.>300 C. ESI-HRMS: calcd. m/z 412.1661 for [M + H]+,found m/z 412.1615 for [M + H]+; 1H NMR (400 MHz, DMSO-d6) delta(ppm) 8.04 (dd, J=6.0 Hz, 2.2 Hz, 1H), 7.65-7.54 (m, 4H), 7.19 (d,J=8.8 Hz, 2H), 6.61 (d, J=8.8 Hz, 1H), 6.48 (d, J=2.4 Hz, 1H), 6.39(dd, J=8.8 Hz, 2.4 Hz, 1H), 3.67 (q, J=7.0 Hz, 4H), 1.18 (t,J=7.0 Hz, 6H). 13 C NMR (100 MHz, DMSO-d6) delta (ppm) 170.36,152.58, 149.65, 140.71, 135.12, 129.84, 128.52, 127.11, 125.28,124.10, 113.10, 108.68, 104.80, 97.57, 84.05, 44.61, 12.65.

According to the analysis of related databases, 4887-80-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Huang, Kun; Han, Defang; Li, Xianglin; Peng, Mengni; Zeng, Xianshun; Jing, Linhai; Qin, Dabin; Dyes and Pigments; vol. 171; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 1849-01-0, 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. 1849-01-0 name is 1-Methyl-1H-benzo[d]imidazol-2(3H)-one, 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.

Prepared from 1 -methyl-1,3-dihydro-2H-benzimidazol-2-one (100 mg, 0.6720 mmol), 2-bromo-5-(difluoromethyl-1,3,4-oxadiazole (134.3 mg, 0.67 mmol), potassiumcarbonate (280 mg, 2.02 mmol), copper iodide (12.9 mg, 0.07 mmol) and trans-/V,/Vdimethylcyclohexane-1,2-diamine (0.02 ml_, 0.1400 mmol) in 1,4-dioxane (5 ml.) at 80 C for2 h. Product obtained as a white solid (65 mg, 0.24 mmol, 36%).[00483] 1H NMR (300MHz, DMSO-d6) Shift = 7.88 (d, J=7.6 Hz, 1H), 7.76 – 7.38 (m,25 1 H), 7.38 – 7.32 (m, 2H), 7.31 – 7.22 (m, 1H), 3.41 (s, 3H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Methyl-1H-benzo[d]imidazol-2(3H)-one, and friends who are interested can also refer to it.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; MCGONAGLE, Alison E.; JORDAN, Allan M.; WASZKOWYCZ, Bohdan; HUTTON, Colin P.; WADDELL, Ian D.; HITCHIN, James R.; SMITH, Kate M.; HAMILTON, Niall M.; (265 pag.)WO2016/97749; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem