Tag: M.W=100-200

Some common heterocyclic compound, 68282-47-3, name is 2-Phenyl-1H-imidazole-4-carbaldehyde, molecular formula is C10H8N2O, 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. category: imidazoles-derivatives

Example 6; Step 1 : 4-Formyl-2-phenyl-imidazole-1-carboxylic acid 4-nitro-benzyl ester 4-Formyl-2-phenylimidazole (624 mg) and sodium hydrogen carbonate (791 mg) were dissolved in dioxane (3.6 mL), THF (3.6 mL) and water (7.2 mL). The 48.7% solution of p-nitrobenzyl chloroformate (PNZCI) in dioxane (2.08 mL) was added to the mixture at room temperature and stirred for 2.5 h. The mixture was diluted with ethyl acetate and washed with brine. The organic layer was dried (MgS04) and concentrated under reduced pressure. The residue was crystallized from ethyl acetate and n-hexane to give the title compound (956 mg, 75%).’H NMR (8, CDCI3) 5.41 (s, 2H), 7.32 (d, 2H, J= 8.6 Hz), 7.40-7. 51 (m, 3H), 7.56-7. 58 (m, 2H), 8.17-8. 20 (m, 2H), 8.22 (s, 1H), 9.97 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 68282-47-3, its application will become more common.

Reference:
Patent; WYETH; WO2003/93277; (2003); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 934-22-5, 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. 934-22-5, name is 6-Aminobenzimidazole, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A dry 50 mL flask was charged with 2-halogenated aromatic aldehyde 1 (1.0 mmol), 1H-benzo[d]imidazol-5-amine (0.133 g,1.0 mmol), cyclohexane-1,3-diones (1.0 mmol), CuI (10 mg), L-proline(6 mg), Cs2CO3 (650 mg) and dioxane (10 mL). The reaction mixture was stirred at reflux for 10-18 h. After completion of the reaction, as indicated by TLC, the solid was filtered off by a fast and hot filtration, and the products of 4 were obtained as pale yellow powder or crystals, when the mixture was allowed to cool down to room temperature.

The chemical industry reduces the impact on the environment during synthesis 6-Aminobenzimidazole. I believe this compound will play a more active role in future production and life.

Reference:
Article; Li, Chao; Zhang, Wen-Ting; Wang, Xiang-Shan; Tetrahedron; vol. 70; 46; (2014); p. 8919 – 8924;,
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. 3752-24-7, name is 4,5,6,7-Tetrahydro-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., Safety of 4,5,6,7-Tetrahydro-1H-benzo[d]imidazole

EXAMPLE 7 1-[1-(3,4-Dichloro-phenyl)-1H-imidazol-4-yl-methyl]-4,5,6,7-tetrahydro-1H-benzoimidazole-, Hydrochloride (1:2) Reaction of 4,5,6,7-tetrahydrobenzimidazole with sodium hydride followed by treatment with 4-chloromethyl-1-(3,4-dichloro-phenyl)-1H-imidazole led after extractive workup and chromatography to the free base of the title compound which was converted into its white hydrochloride salt. Mp.>250 C. (MeOH/Et2O), MS: m/e=346 (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; Alanine, Alexander; Buettelmann, Bernd; Heitz Neidhart, Marie-Paule; Jaeschke, Georg; Pinard, Emmanuel; Wyler, Rene; US2002/151715; (2002); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 16042-25-4, A common heterocyclic compound, 16042-25-4, name is 2-Imidazolecarboxylic 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 stirred suspension of 1H-imidazole-2-carboxylic acid (3.00 g, 26.8 mmol) in anh. DCM (45 mL)cooled to 0 C under N2 was added oxalyl chloride (4.5 mL, 53.5 mmol) followed by addition of DMF (2 drops). The reaction was allowed to warm to rt and stir overnight. A further portion of oxalylchloride (1.13 mL, 13.4 mmol) and DMF (1 drop) was added and the reaction stirred for 4 hr.Volatiles were then removed in vacuo and the residual oxalyl chloride was removed by coevaporationwith toluene to afford acid chloride as a colourless solid. The solid was then addedportionwise to conc NH4OH (15 mL) chilled to 0 C. Volatiles were then removed in vacuo.Residual volatiles were coevaporated with toluene to obtain dry material (25: 75 startingmaterial:product). The crude was retreated to the reaction with oxalyl chloride (1.7 mL, 20.1 mmol)using the above procedure. The solid obtained was then washed with water (2 x 20 mL) and driedin vacuo to obtain a tan solid (2.16 g, 73%) that was used without further purification. LCMS (Waters Atlantis: Gradient Method 2): Rt = 1.44 min, 99 A% 254 nm, [M + H]+ = 112.2. 1H NMR(600 MHz, DMSO-d6) delta 12.95 (s, 1H), 7.73 (s, 4H), 7.43 (s, 1H), 7.23 (br s, 1H), 7.04 (br s, 1H).

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; Jarrad; Debnath; Miyamoto; Hansford; Pelingon; Butler; Bains; Karoli; Blaskovich; Eckmann; Cooper; European Journal of Medicinal Chemistry; vol. 120; (2016); p. 353 – 362;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 15965-54-5, 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. 15965-54-5 name is 2-Chloro-5-methoxy-1H-benzo[d]imidazole, 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 2-chloro-5-methoxy-1H-benzo[djimidazole (13.04 mg, 0.071 mmol) and Intermediate I-i (20 mg, 0.059 mmol) was added toluene (0.75 mL) and EtOH (0.25 mL). The reaction mixture was stirred at room temperature until solids are dissolved, then [1,1 ?-Bis(diphenylphosphino)ferrocenej dichloropalladium (II) complex with dichloromethane (1:1) (5.83 mg, 7.14 imol) was added. The flask was degassed andflushed with argon. Finally sodium carbonate (0.059 mL, 2M, 0.119 mmol) was added dropwise. The reaction vessel was sealed and bubbled with argon for 5 mm, then placed in microwave reactor at 140 C for 30 mm. The reaction mixture was cooled to room temperature and was diluted with EtOAc and water, extracted with EtOAc (3X). The combined organic layer was washed with brine, dried with Mg504 and concentrated. Thecrude sample was purified with a preparative HPLC (method A, 30-100% B in 8 mm.). The desired fractions were placed in a SpeedVac overnight to remove solvent, then lyophilized to give Example 50 (6 mg, 0.016 mmol, 27.5 % yield). ?H NMR (acetonitrile-d3, 400MHz): = 8.77 (br. s., 2H), 7.70 (s, 3H), 7.27-7.39 (m, 1H), 7.05-7.18 (m, 1H), 3.90 (s, 3H), 2.65 ppm (s, 3H). ?9F NMR (acetonitrile-d3, 376MHz):= -76.64 (br. s., 3F), -90.69 ppm (s, 2F). LC-MS: method C, RT = 1.78 mm, MS (ESI) m/z: 357.0 (M+H). Analytical HPLC purity (method A): 98%

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-5-methoxy-1H-benzo[d]imidazole, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ZHANG, Xiaojun; PRIESTLEY, Eldon Scott; BATES, J. Alex; HALPERN, Oz Scott; REZNIK, Samuel Kaye; RICHTER, Jeremy M.; (1137 pag.)WO2018/13774; (2018); 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. 934-22-5, name is 6-Aminobenzimidazole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 934-22-5

General procedure: A dry 50 mL flask was charged with 2-halogenated aromatic aldehyde 1 (1.0 mmol), 1H-benzo[d]imidazol-5-amine (0.133 g,1.0 mmol), cyclohexane-1,3-diones (1.0 mmol), CuI (10 mg), L-proline(6 mg), Cs2CO3 (650 mg) and dioxane (10 mL). The reaction mixture was stirred at reflux for 10-18 h. After completion of the reaction, as indicated by TLC, the solid was filtered off by a fast and hot filtration, and the products of 4 were obtained as pale yellow powder or crystals, when the mixture was allowed to cool down to room temperature.

According to the analysis of related databases, 934-22-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Li, Chao; Zhang, Wen-Ting; Wang, Xiang-Shan; Tetrahedron; vol. 70; 46; (2014); p. 8919 – 8924;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 68282-47-3, 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. 68282-47-3 name is 2-Phenyl-1H-imidazole-4-carbaldehyde, 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 2-phenyl-1H-imidazole-4-carbaldehyde (1.73 g) in ethanol (30 mL) was added 40% methylamine-methanol solution (2.36 g) and the mixture was stirred at 65C for 1 hr. The mixture was allowed to cool to room temperature, sodium borohydride (571 mg) was added and the mixture was stirred for 30 min. 1 mol/L Hydrochloric acid was added to the reaction mixture, and the mixture was concentrated under reduced pressure. A saturated aqueous sodium hydrogen carbonate solution was added to the residue, and the mixture was extracted with tetrahydrofuran. The extract was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent: ethyl acetate-methanol=1:0?4:1) and dissolved in methanol (10 mL). A 4 mol/L hydrogen chloride-ethyl acetate solution (5 mL) was added, and the mixture was concentrated under reduced pressure. The residue was crystallized from ethyl acetate to give the title compound as colorless crystals (yield 1.06 g, yield 41%). 1H-NMR(DMSO-d6)delta:2.62(3H,s), 4.33(2H,s), 7.55-7.73(3H,m), 7.83(1H,s), 8.21(2H,br), 9.64(2H,br), 2H not detected.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Phenyl-1H-imidazole-4-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2196459; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 705-09-9, These common heterocyclic compound, 705-09-9, name is 2-(Difluoromethyl)-1H-benzo[d]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.

Step 1 : To a solution of 3a in DMF was added NaH with ice-bath. The resulting mixture was stirred for 15min. at 0-5 0C and was added 1g. The reaction mixture was stirred at r.t. over night and evaporated to remove DMF. The residue was purified by column chromatography (PE:EA=1:2) to give 3b.

Statistics shows that 2-(Difluoromethyl)-1H-benzo[d]imidazole is playing an increasingly important role. we look forward to future research findings about 705-09-9.

Reference:
Patent; TYROGENEX, INC.; LIANG, Congxin; LI, Zhigang; WO2010/56320; (2010); A2;,
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. 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, A new synthetic method of this compound is introduced below., HPLC of Formula: C5H6N2O2

(1) To a solution of methyl 4-imidazole carboxylate (a-1) (5.0 g, 39 mmol) in tetrahydrofuran (THF) (100 mL), p-trifluoromethyl benzyl alcohol (a-2) (6.5 mL, 48 mmol) and triphenylphosphine (PPh3) (12 g, 47 mmol) were added and after adding a toluene solution (25 mL, 48 mmol) of 1.9 mol/L diisopropyl azodicarboxylate (DIAD) dropwise, the resulting mixture was stirred at room temperature for 3 hours. After distilling off the solvents under reduced pressure, the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=50:500:100) and purified again by silica gel (NH) column chromatography (n-hexane:ethyl acetate=90:1050:50) to give methyl 1-[4-(trifluoromethyl)benzyl]-1H-imidazole-5-carboxylate (a-3) (amount, 7.7 g; yield, 69%).

The synthetic route of 17325-26-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KAKEN PHARMACEUTICAL CO., LTD.; IKEGAMI, Satoru; WATANABE, Atsushi; HIRANO, Kimio; OHYAMA, Tadashi; (56 pag.)US2016/130232; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1792-40-1, 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. 1792-40-1, name is 2-Methyl-5-nitro-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 5-nitrobenzimidazole (1.0 G, 5.6 MMOL) in acetone (50 mL) was added potassium carbonate (1.0 g), followed by alkyl halide (1.2-1. 5 equivalents). The mixture was stirred under nitrogen at rt, then partitioned between ethyl acetate and water after TLC showed completion of the reaction. The organic phase was washed with brine, dried over sodium sulphate and concentrated in vacuo to give a mixture of 1-ALKYL- 5-NITRO-2-METHYLBENZIMIDAZOLE and 1-alkyl-6-nitro-2-methylbenzimidazole, which were dissolved in ethanol-THF (100 mL, 2: 1) and hydrogenated over 5% Pd-C under atmosphere pressure for 8h. After filtration through celte, the filtrate was evaporated to give a yellow solid that was separated with flash chromatography (Methanol-DCM gradient elution). 1-Alkyl-5-aminobenzimidazole and 1-alkyl-6-aminobenzimidazole were obtained as yellow solid or thick syrup.; 5-Amino-1, 2-DIMETHYLBENZIMIDAZOLE (XDS01191B, XDS02082B): Yellow solid, mp 126-127C (LIT. 128C, [23] ). TLC single spot at Rf 0.30 (5% methanol/DCM) ;’H NMR (270 MHz, DMSO): 6 7.08 (1H, d, J = 8.7 Hz, 7-H), 7.65 (1H, d, J = 1.5 Hz, 4-H), 6.50 (1H, dd, J = 8.7, 1.5 Hz, 6-H), 4.63 (2H, broad, NH2), 3.58 (3H, s, NCH3), 2.39 (3H, s, CH3). 6-Amino-1, 2-DIMETHYLBENZIMIDAZOLE (XDS01191A, XDS02082A): Yellow solid. TLC single spot at Rf 0.33 (5% methanol/DCM) ;’H NMR (270 MHz, DMSO): 6 7. 13 (1H, d, J = 8.4 Hz, 4-H), 6.48 (1H, d, J = 2. 0 Hz, 7-H), 6.43 (1H, dd, J = 8.4, 2.0 Hz, 5-H), 4.83 (2H, broad, NH2), 3.53 (3H, s, NCH3), 2.39 (3H, s, CH3).

The synthetic route of 2-Methyl-5-nitro-1H-benzo[d]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; STERIX LIMITED; WO2004/37251; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem