Category: imidazoles-derivatives

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. 1003-91-4, name is 2,4,5-Tribromo-1-methylimidazole, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 1003-91-4

To a solution of Example 69b (84 g, 263.3 mmol) in dry THF (2L) was added EtMgBr (88 mL, 263.3 mmol, 3.0M in ether) slowly under N2.The reaction was stirred at r.t. for 2 hours. Then about 2.0L water was added and filtered concentrated and the residue was extracted with EtOAc (50 mL * 2). The combined organic phase was washed with brine, dried over Na2S04, filtrated and concentrated under reduced pressure to give the crude product which was further purified by silica gel chromatography to give the pure product Example 69d (14.0 g) as white solid ‘HNMR (400 MHz, Chloroform- ) delta 7.48 (s, 1H), 3.63 (s, 3H). Example 69c (14.0g) as white solid. NMR (400 MHz, Chloroform- ) delta 6.94 (s, 1H), 3.60 (s, 3H). A solution of Example 69c&d (2.4 g, 10.0 mol) in ether (100 mL) was cooled to -78 C. under nitrogen atmosphere and then a 2.5 M n-BuLi solution in hexane (4.0 mL, 10.0 mol) added dropwise over 15 mins. The mixture was stirred at -78 C. for 30min and then DMF (2.0 mL) was added dropwise over 15 min. The mixture was stirred at -78 C. for 30min and quenched with saturated IN HQ (50 mL) at -78 C. The residue was extracted with EtOAc (50 mL * 2). The combined organic phase was washed with brine, dried over Na2S04, filtrated and concentrated under reduced pressure to give the crude product which was further purified by silica gel chromatography to give the pure product Example 69e (1.8 g, yield 95%) as yellow solid. NMR (400 MHz, Chloroform-d) delta 9.77 (d, J = 0.9 Hz, 1H), 7.51 (s, 1H), 3.93 (s, 3H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1003-91-4.

Reference:
Patent; FRONTHERA U.S. PHARMACEUTICALS LLC; JIN, Bohan; DONG, Qing; HUNG, Gene; (212 pag.)WO2017/218960; (2017); 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 26832-08-6 as follows. Recommanded Product: 26832-08-6

In a dried 125 mL, three-neck flask fitted with a magnetic stirrer, temperature probe, a reflux condenser, and a positive nitrogen atmosphere set-up was charged with 4-imidazole carboxamide 2.0 gm (18 mmol), acetonitrile 25 ml, and POCl3 6.6 gm (43.2 mmol). The brown slurry was agitated and heated to reflux. The reaction mixture was maintained at reflux for at least 15 hrs. Then the excess POCl3 was distilled under reduced pressure. After aqueous work up, the reaction mixture was adjusted to a pH of 9-11 using 25% sodium hydroxide, and extracted with 4×70 ml ethyl acetate. The combine ethyl acetate extracts were treated with 20 gm silica gel, distilled under pressure to remove ethyl acetate and to afford 4-cyanoimidazole as a white solid. After drying the 4-cyanoimidazole weighed 1.1 gm (65.9% yield): HPLC purity, >99.0 area %; 1H NMR (300 MHz, DMSO-D6) delta 7.89 (s, 1H), 8.08 (s, 1H); 13C NMR (300 MHz, DMSO-D6) delta 111.8, 116.0, 127, 138.1.

According to the analysis of related databases, 26832-08-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ampac Fine Chemicals LLC; US2009/292122; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 492-98-8,Some common heterocyclic compound, 492-98-8, name is 1H,1’H-2,2′-Biimidazole, molecular formula is C6H6N4, 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.

2,2′-Biimidazole (0.27 g, 2 mmol) and NaOH (0.32 g, 8 mmol) were placed in a 100 mL round bottomed flask with 20 mL of acetonitrile. The mixture was stirred at room temperature for two hours. 2-Picolyl chloride hydrochloride (0.65 g, 4 mmol) in acetonitrile (20 mL) was added to the mixture and refluxed for 24 h at 50-60 C. The reaction was monitored with TLC and upon completion the solvent was removed by rotary evaporation. The residue was dissolved in water (50 mL) and extracted with methylene chloride (30 mL * 3). Organic layers were combined, dried over anhydrous MgSO4 and rotary evaporated to obtain the pale brown color powder as the product. Yield: 0.25 g (40%); mp 180-183 C; 1H NMR (deltaH; CDCl3, 400 MHz): 8.53 (d, 2H), 7.53 (t, 2H), 7.15 (t, 2H), 7.12 (s, 2H), 7.07 (s, 2H), 7.05 (d, 2H), 5.87 (s, 4H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1H,1’H-2,2′-Biimidazole, its application will become more common.

Reference:
Article; Aakeroey, Christer B.; Wijethunga, Tharanga K.; Desper, John; Journal of Molecular Structure; vol. 1072; 1; (2014); p. 20 – 27;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 57090-88-7, name is 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 57090-88-7, Formula: C4H3N3

General procedure: A solution of 4-cyano-1H-imidazole (1000 mg, 10.74 mmol), 4-iodo -2-(trifluoromethyl)pyridine (3800 mg,14 mmol), (1R,2R)-N1,N2-dimethyl cyclohexane -1,2-diamine (150 mg, 1.07 mmol), CuI (200 mg, 1.07 mmol) and Cs2CO3 (7000 mg, 21.5 mmol) in 20 mL anhydrous DMF was stirred at 100 oC for 2 hours. The reaction mixture was cooled to room temperature and poured into 200 mL water. The mixture was extracted with ethyl acetate (80 mL*3). The organic layer were combined, washed by brine, dried by Na2SO4 and evaporated. The crude product was purified by silica flash column to afford compound 2 as white solid(1.5 g, 59percent yield).

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:
Article; Zheng, Qiangang; Chen, Ziqi; Wan, Huixin; Tang, Shuai; Ye, Yan; Xu, Yuan; Jiang, Lei; Ding, Jian; Geng, Meiyu; Huang, Min; Huang, Ying; Bioorganic and Medicinal Chemistry Letters; vol. 28; 23-24; (2018); p. 3808 – 3812;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

4856-97-7, name is (1H-Benzoimidazol-2-yl)methanol, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. SDS of cas: 4856-97-7

The method for synthesizing 2-aldehyde benzimidazole in this example is as follows2-Hydroxymethylbenzimidazole (0.1 mol, 14.8 g)The rhodium complex (10-4 mol, 0.0577 g) in Example 1 was added to the reaction vessel.Hydrogen peroxide (30%, 0.3 mol, 9.1 ml) was slowly added to the reaction vessel with stirring.The reaction temperature was controlled at 50C for several hours.The reaction solution was concentrated under reduced pressure,Obtain a solid product,The solid product was dissolved in dichloromethane and subjected to silica gel column chromatography.Get pure product2-aldehyde benzoimidazole 8.32 g,Yield 57%.

The synthetic route of 4856-97-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Lingnan Normal University; Liu Shenggui; Pan Rongkai; Li Guobi; Su Wenyi; (9 pag.)CN107445998; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 872-82-2, name is 2-(1H-Imidazol-5-yl)ethanol, molecular formula is C5H8N2O, 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: 2-(1H-Imidazol-5-yl)ethanol

In an ice bath, add slowly to the 4-hydroxyethyl imidazole obtained in Step 1.3 mL of thionyl chloride.After the addition was complete, the mixture was warmed to room temperature and stirred to give a yellow solution.Raise the temperature to 70 C for 1 h.The brown clear solution was removed by rotary evaporation to remove the remaining thionyl chloride to give a brown viscous liquid.Add a small amount of water to dissolve,The pH was adjusted to basic with aqueous sodium carbonate solution and extracted three times with ethyl acetate.The combined organic phases are dried over anhydrous sodium sulfate.Concentrated yellow oily liquid.The crude product is separated by column chromatography.Concentrated 1.3 g of a yellow oily solution was used directly for the next reaction.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 872-82-2, its application will become more common.

Reference:
Patent; Tongwei Co., Ltd.; Zhao Yan; Zhi Yonggang; Zhang Fengping; Cao Jun; Liu Yaomin; Long Yuande; (9 pag.)CN105367500; (2018); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 72-40-2, 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 72-40-2 as follows.

Example 1 Preparation of Temozolomide (1) 5-Amino-1H-imidazole-4-carboxamide.HCl (4) (25 g, 0.154 mol) (Aldrich 16,496-8), CH2Cl2(0.6 L) and Et3N (45 mL) (Aldrich, 13,206-3) were placed into a dry 2-liter, three-necked flask equipped with dropping funnel, a gas inlet tube, a gas outlet tube, reflux condenser and mechanical stirrer, and maintained under a positive pressure of nitrogen at ambient temperature. The mixture was stirred, and a solution of 400 mL of 4-nitrophenyl chloroformate (34 g, 0.169 mol) (Aldrich, 16,021-0) in CH2Cl2 was added dropwise. The reaction mixture was stirred vigorously for 4 hours and then left to stand for 18 hours at room temperature. The precipitate was collected by vacuum filtration and washed with H2O (1.5 L) to afford the product (3) as a pale yellow solid (42 g, 0.144 mol). 1H NMR (400 MHz, DMSO-d6, delta): 8.40 (d, 2H), 7.83 (s, 1H), 7.74 (d, 2H), 7.08 (bs, 1H), 6.95 (bs, 1H), 6.52 (s, 2H).

According to the analysis of related databases, 72-40-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Schering Corporation; US2002/133006; (2002); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 1003-21-0, name is 5-Bromo-1-methyl-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. COA of Formula: C4H5BrN2

Intermediate 7: Step b (1-Methyl-1H-imidazol-5-yl)(4-nitrophenyl)methanone To a solution of 5-bromo-1-methyl-1H-imidazole (3.22 g, 19.98 mmol) in DCM (15 mL) was added ethyl magnesium bromide (6.66 mL, 19.98 mmol, 3.0 M in diethyl ether) dropwise over a 10 minute period. The resulting orange-red solution was stirred at room temperature for 15 minutes, cooled in an ice bath to 0 C. and N-methoxy-N-methyl-4-nitrobenzamide (3.5 g, 16.65 mmol, Intermediate 7: step a) dissolved in DCM (10 mL) was added dropwise. The ice bath was removed and the solid suspension stirred at room temperature for 48 hours. Water was added followed by 6 M aqueous HCl to a neutral pH (pH=6-7). The aqueous mixture was extracted with DCM, dried over Na2SO4, filtered and concentrated. Et2O was added and the mixture sonicated. The precipitate was collected by filtration and dried to provide the title compound as a tan solid.

The synthetic route of 5-Bromo-1-methyl-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LEONARD, KRISTI A.; BARBAY, KENT; EDWARDS, JAMES P.; KREUTTER, KEVIN D.; KUMMER, DAVID A.; MAHAROOF, UMAR; NISHIMURA, RACHEL; URBANSKI, MAUD; VENKATESAN, HARIHARAN; WANG, AIHUA; WOLIN, RONALD L.; WOODS, CRAIG R.; FOURIE, ANNE; XUE, XIAOHUA; CUMMINGS, MAXWELL D.; US2015/105369; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 120781-02-4, name is Methyl 2-bromo-1-methyl-1H-imidazole-5-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 120781-02-4, SDS of cas: 120781-02-4

Methyl 2-(4-(hydroxymethyl)phenyl)-1-methyl-1H-imidazole-5-carboxylate (44). To a solution of methyl2-bromo-1-methyl-1H-imidazole-5-carboxylate5 (515 mg, 2.35 mmol, 1.0 eq) in dioxane (72 mL) was added Pd(PPh3)4 (133 mg, 0.115 mmol, 0.049 eq). The mixture was stirred for 15 min at room temperature before 4-hydroxymethylbenzeneboronic acid (357 mg, 2.35 mmol, 1.0 eq) in 22 mL H2O and K2CO3 (390mg, 2.82 mmol, 1.2 eq) were added. The reaction mixture was heated to 60 C and stirred for 16 h. The solvent was evaporated and the residue was diluted with EtOAc and H2O. The phases were separated and the product was extracted with EtOAc (3x 20 mL). The combined organic extracts were dried overNa2SO4 and the solvent was removed under reduced pressure. The crude product was purified by flash chromatography (10-100% EtOAc linear gradient in hexanes) providing the corresponding benzylicalcohol in 81% (470 mg) yield.

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, Methyl 2-bromo-1-methyl-1H-imidazole-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Fuerst, Rita; Yong Choi, Jun; Knapinska, Anna M.; Smith, Lyndsay; Cameron, Michael D.; Ruiz, Claudia; Fields, Gregg B.; Roush, William R.; Bioorganic and Medicinal Chemistry; vol. 26; 18; (2018); p. 4984 – 4995;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 3012-80-4, name is 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde, 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 3012-80-4, category: imidazoles-derivatives

2- hydroxymethyl-l -methyl-1 H-benzimidazole (Compound 49a)A suspension of l -methyl-2-formyl-l H-benzimidazole (500 mg, 3.12 mmol) and NaBH4 (134 mg, 3.43 mmol) in anhydrous THF (25 ml) was stirred for 24 hours at r.t.. The reaction mixture was quenched with water, extracted with EtOAc, dried over Na2S04 and evaporated to dryness in vacuo. The crude was purified by automated flash chromatography (Horizon.(R).TM – Biotage) eluting with CHC13 – 1.7M NH3 sol. in MeOH 100:2 giving the title product as white solid. Yield: 50.4 percent. MS: [ +H]+ = 163.5

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; RECORDATI IRELAND LIMITED; LEONARDI, Amedeo; MOTTA, Gianni; RIVA, Carlo; GUARNERI, Luciano; GRAZIANI, Davide; MARINONI, Fabio; BETTINELLI, Ilaria; WO2011/29633; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem