Tag: M.W=100-200

Some common heterocyclic compound, 939-70-8, name is 1-(1H-Benzo[d]imidazol-2-yl)ethanone, molecular formula is C9H8N2O, 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: 1-(1H-Benzo[d]imidazol-2-yl)ethanone

General procedure: To the solution of 2-acetyl benzimidazole 1 (0.01 mol) in MeOH (20 mL) was added 10% aqueous NaOH (2 mL) at 0C with stirring. Then, the solution of aromatic aldehydes (0.01 mol) in MeOH was added drop-wise. The reaction mixture was magnetically stirred for 12 h. After completion of the reaction (monitored by TLC) the reaction mixture was poured over crushed ice. The separated solid was filtered, washed with water and dried. The residue was purified by column chromatography (silica gel with 10% ethyl acetate in petroleum ether) to afford pure benzimidazole derived chalcone 2a-m.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 939-70-8, its application will become more common.

Reference:
Article; Meshram, Gangadhar A; Vala, Vipul A.; Wagh, Pramod A.; Deshpande, Shruti S.; Indian Journal of Chemistry – Section B Organic and Medicinal Chemistry; vol. 55B; 5; (2016); p. 613 – 623;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 7152-24-1, 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. 7152-24-1 name is 2-(Methylthio)benzimidazole, 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.

the following compound was prepared from 2-(3-nitrophenylamino)-benzoyl chloride and 2-methylthiobenzimidazole: 5-(3-nitrophenyl)-benzimidazo-[2,1-b]-quinazolin-12(5H)-one STR14 Yield: 62% of theory, melting point 294 C.; N calculated 15.72%; N found 15.73%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(Methylthio)benzimidazole, and friends who are interested can also refer to it.

Reference:
Patent; Troponwerke GmbH & Co.; US4539402; (1985); 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. 75370-65-9, name is 4-Amino-1H-benzo[d]imidazol-2(3H)-one, A new synthetic method of this compound is introduced below., Quality Control of 4-Amino-1H-benzo[d]imidazol-2(3H)-one

To a solution of 29b (0.6g, 2.28 mmol) in THF (20 mL) was added CDI (2.1 mol eq, 0.78g) and the mixture was heated at 70C for 6h. The reaction mixture was evaporated, water was added and the aqueous phase was extracted with EtOAc (3×25 mL). The recombined organic phases were anhydrified over Na2SO4 and evaporated at reduced pressure (yellow oil, 0.72 g, 88% yield). The oil obtained was dissolved in DMF (20 mL) and the bicyclic amine la was added (0.8 mol eq, 0.24g), then the mixture obtained was heated at 100C overnight. The solvent was removed at reduced pressure and the residue was purified by chromatography (8:2 EtOAc:MeOH) to obtain the product as a pale yellow solid (0.088g, 0.158 mmol, 10% Yield). 1HNMR (DMSO, 400 MHz) delta 2.27 (s, 6H), 2.73 (t, 2H), 4.25 (d, 2H, j=6), 4.46 (t, 2H), 6.60 (d, 1H), 6.83 (m, 2H), 7.01 (d, 1H), 7.43 (d, 1H), 7.80 (d, 1H), 8.60 (s, 1H), 10.02 (bs, 1H), 10.62 (bs, 1H). [M+1] 439.02 (C19H21F3N6O3 requires 438.40).

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; PHARMESTE S.R.L.; NAPOLETANO, Mauro; TREVISANI, Marcello; PAVANI, Maria Giovanna; FRUTTAROLO, Francesca; WO2011/120604; (2011); 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. 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., name: 2-Chloro-1H-benzo[d]imidazole

Step 1: N-Phenyl-1H-benzo[d]imidazol-2-amine 2-Chloro-1H-benzo[d]imidazole (5 g, 32.8 mmol) was dissolved in N-methyl-2-pyrrolidone (NMP) (50 mL) and treated with aniline (3.3 mL, 36.1 mmol), followed by methanesulfonic acid (2.4 mL, 37.0 mmol). The resulting mixture was purged with N2 for 5 min, then heated at 100 C. for 18 h. The mixture was cooled to room temperature (?22 C.) then poured into a stirred mixture of saturated NaHCO3 (aq) (100 mL) in water (400 mL). The resulting suspension was extracted with ethyl acetate (2*75 mL). The organic phases were combined and washed sequentially with water (3*75 mL) and brine (75 mL), then dried over MgSO4, filtered, and concentrated in vacuo to afford an orange oil. The residue was dissolved in methyl tert-butyl (MTBE) (ca. 50 mL) and the product crystallised by slow addition of isohexane (ca. 25 mL) with periodic sonication. The resultant slurry was stirred at room temperature for 1 h, then the precipitate was collected by filtration, washing with MTBE/isohexane (1:1, 3*10 mL), and drying in vacuo to afford N-phenyl-1H-benzo[d]imidazol-2-amine (6.25 g, 89%). The precipitate was a pale pink crystalline solid.

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; Universal Display Corporation; LIN, Chun; Ji, Zhiqiang; Ma, Bin; (139 pag.)US2018/337344; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 41716-18-1, 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. 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a suspension of [1-METHYL-IMIDAZOLE-4-CARBOXYLIC ACID (11.] 4g, 90 [MMOL)] in THF (500ml) at [0°C,] was added drop-wise a solution of lithium aluminium hydride [(1 M] in THF, [117ML,] 117 [MMOL)] and the mixture was stirred at room temperature overnight and then at [50°C] for 1 hour Water (3 [ML)] was added followed by [NA2SO4] and the mixture was filtered through [CELITETM.] The filtrate was concentrated under reduced pressure to afford the title compound as a solid [(8G,] 78.95percent) ;’H NMR (300 MHz, [CDCI3)] 6 ppm: 7.25 (s, 1 H), 6. 7 (s, 1H), 5.25 (m, 1H), 4.4 (s, 2H), 3.45 (s, 3H).

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

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2004/13138; (2004); A2;,
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 4857-06-1 as follows. Application In Synthesis of 2-Chloro-1H-benzo[d]imidazole

Example 1N-(4-Fluoro-3-trifluoromethyl-benzyl)-N-(1-methyl-1H-benzimidazol-2-yl)-benzenesulfonamide (Compound No.15)Step A: 2-Chloro-1-methyl-1H-benzimidazoleTo a solution of 2-chloro-1H-benzimidazole (5.03 g, 33.0 mmol) in anhydrous DMF (33 mL) at 0 C. was added portion-wise 95% NaH (871 mg, 36.3 mmol). The ice bath was removed and the resulting mixture was stirred at room temperature for 1 h. Iodomethane (4.68 g, 33.0 mmol) was added and the resulting mixture was stirred at room temperature overnight. The resulting mixture was then diluted with water, and the resulting precipitate was collected by filtration and purified by recrystallization from hexane to yield 2-chloro-1-methyl-1H-benzimidazole. MS 167 (M+1)+

According to the analysis of related databases, 4857-06-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jetter, Michele C.; Macielag, Mark J.; Xia, Mingde; Xu, Xiaoqing; US2011/3801; (2011); A1;,
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 38993-84-9 as follows. Application In Synthesis of (1-Methyl-1H-imidazol-5-yl)methanol

To the solution of (1 -methyl- lH-imidazol-5-yl)methanol (570 mg, 5 mmol) in dioxane (50 niL) in a 250 mL round bottom flask, was added NCS (815 mg, 6 mmol). The resulting mixture was stirred at room temperature overnight. Dioxane was removed under vacuum.

According to the analysis of related databases, 38993-84-9, the application of this compound in the production field has become more and more popular.

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

Application of 39070-14-9, A common heterocyclic compound, 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, molecular formula is C5H7N3O3, 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.

300 mg of 3 (1 eq., 0.55 mmol), 86 mg of 1 (1 eq., 0.55 mmol),326 mg of Cu(OAc)2·H2O, 18 mg of potassium iodide (0.2 eq.,0.11 mmol) and 6 mg of Pd(OAc)2 were dissolved in 3 mL of dimethylsulfoxide and 12 mL acetonitrile. The reaction vessel was set under anatmospheric pressure of carbon monoxide (CAUTION: highly toxic) andshortly warmed with a hot water bath (40 C). After 1 h the reactionmixture was taken up in EtOAc and washed with sat. NaHCO3 andwater. The combined aqueous solutions were washed with EtOAc andthe combined organic solutions were washed with brine, dried overMgSO4 and the solvent was removed under reduced pressure. The crudeproduct was dried in vacuo overnight. Purification was performed usingcolumn chromatography (EtOAc/petrol ether 9:1). Yield: 160 mg(40%). 1H NMR (500 MHz, DMSO-d6) delta 9.35 (s, 1H), 8.65 (s, 1H), 8.41(s, 1H), 8.23 (s, 2H), 7.84 (s, 1H), 7.54 (dd, J = 8.9, 5.0 Hz, 1H), 7.45(t, J = 8.7 Hz, 1H), 7.38 (s, 1H), 7.28 (s, 1H), 6.15 (d, J = 6.6 Hz, 1H),5.30 – 5.19 (m, 2H), 4.52 (t, J = 10.9 Hz, 1H), 3.96 (s, 3H), 3.10 (dd,J = 23.1, 11.6 Hz, 2H), 2.23 (d, J = 11.4 Hz, 2H), 2.15 – 2.06 (m, 2H),1.73 (d, J = 6.6 Hz, 3H), 1.43 (s, 9H) ppm. ESI-MS (M + Na): calc:755.19 found: 755.39.

The synthetic route of 39070-14-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Berger, Walter; Bielec, Bjoern; Heffeter, Petra; Keppler, Bernhard K.; Kowol, Christian R.; Schueffl, Hemma; Terenzi, Alessio; Bioorganic Chemistry; vol. 99; (2020);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 1072-84-0, A common heterocyclic compound, 1072-84-0, name is 1H-Imidazole-4-carboxylic acid, molecular formula is C4H4N2O2, 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.

To a mixture of 1H-imidazole-4-carboxylic acid (5.00 g, 44.6 mmol, CAS1072-84-0) in MeOH (50 mL) was added SOCl2 (10.6 g, 89.2 mmol, 6.47 mL). The reaction mixture was stirred at 70 C. for 16 hours. On completion, the reaction mixture was concentrated in vacuo to give the title compound (5.60 g, 99% yield) as white solid. The residue was used to the next step directly without further purification. 1H NMR (400 MHz, DMSO-d6) delta 9.29-9.25 (m, 1H), 8.37 (s, 1H), 3.87 (s, 3H).

The synthetic route of 1072-84-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); 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. 2849-93-6, name is 1H-Benzimidazole-2-carboxylic acid, A new synthetic method of this compound is introduced below., Formula: C8H6N2O2

General procedure: The aryl carboxylic acid (1.1 eq.) and TBTU (1.2) were suspended in anhydrous THF (11 mL/mmol eq.) at r.t. under N2 atmosphere. DiPEA (2.4 eq.) was then added dropwise to the reaction mixture,followed by the different (thieno[2,3-d]pyrimidin-4-yl)-hydrazine (8a-d or f-i) (1 eq.) dissolved in anhydrous THF (11 mL/mmol eq.). The mixture was stirred at r.t. for 4 h, then concentrated under vacuum. The residue was dissolved in EtOAc (30 mL/mmol eq.), washed with water (30 mL/mmol eq.), saturated NaHCO3 solution (30 mL/mmol eq.), and finally with brine (30 mL/mmol eq.). The organic phase was concentrated under vacuum after drying over MgSO4. The crude residue was purified by recrystallisation or flash column chromatography.

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; Bassetto, Marcella; Leyssen, Pieter; Neyts, Johan; Yerukhimovich, Mark M.; Frick, David N.; Brancale, Andrea; European Journal of Medicinal Chemistry; vol. 123; (2016); p. 31 – 47;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem