Author: Jessica.F

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

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

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

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

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. 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 68282-53-1

A solution of 3-methoxy-/V-((4-methyl-1 H-imidazol-5-yl)methylene)aniline in ethanol was prepared by heating a solution of 4-methyl-1 /-/-imidazole-5-carbaldehyde (0.1 10 g; 0.999 mmol) and 3-methoxyaniline (0.1 15 mL; 1.023 mmol) in ethanol (0.7 mL) at 65C for 24 h. The formation of the imine was quantitative and the solution was used without further purification. ESI/APCI (+): 216 (M+H). ESI/APCI (-): 214 (M-H).

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 68282-53-1.

Reference:
Patent; KATHOLIEKE UNIVERSITEIT LEUVEN; BARDIOT, Dorothee; CARLENS, Gunter; DALLMEIER, Kai; KAPTEIN, Suzanne; McNAUGHTON, Michael; MARCHAND, Arnaud; NEYTS, Johan; SMETS, Wim; WO2013/45516; (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. 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, A new synthetic method of this compound is introduced below., Computed Properties of C5H6N2O

lb lb. 3-({4-[(2-Hydroxyethyl)(methyl)carbamoyl]phenyl}({l-[(4-methyl-lH-imidazol-5-yl)methyl]piperidin-4-ylidene})methyl)benzamide 3-({4-[(2-Hydroxyethyl)(methyl)carbam benzamide (79.0 mg, 0.2 mmol) was dissolved in 1 ,2-dichloroethane (2 mL) and acetic acid (57 muIota_, 1 .0 mmol) was added followed by 5-methylimidazole-4-carboxaldehyde (44.0 mg, 0.4 mmol) and NaBH(OAc)3 (169 mg, 0.8 mmol). The reaction was stirred at 50C for 48 h. The crude was purified by flash chromatography (ethyl acetate, ethyl acetate/methanol 75:25) to give the title compound as a crude material. This material was then purified by preparative HPLC (X-bridge column, 50 mM NH4HCO3 as mobile phase, CH3CN from 10 to 40) to give 5 mg of the title compound. MS m/z 488 [M+H]+.

The synthetic route of 68282-53-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMNOVO AB; VON MENTZER, Bengt; STARKE, Ingemar; BRANDT, Peter; (24 pag.)WO2016/99394; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 872-82-2,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.

General procedure: A mixture of imidazole derivatives (4a-c, 10mmol), 4-amino-6-chloropyrimidine (1.30g, 10mmol), and K2CO3 (2.07g, 15mmol, for 5a) or Cs2CO3 (3.91g, 12mmol, for 5b-c) was stirred in DMF (20mL) at 100C (for 5a) or at 140C (for 5b-c) for 12h. Water (100mL) was then added. The mixture was extracted with EtOAc (3×50mL). The organic layer was separated and dried over Na2SO4. Removal of the solvents produced a residue which was purified using column chromatography and eluted with a mixture of MeOH:CH2Cl2 (1:30, v:v) to afford 5a-c.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(1H-Imidazol-5-yl)ethanol, its application will become more common.

Reference:
Article; Xu, Yi-xiang; Wang, Huan; Li, Xiao-kang; Dong, Sheng-nan; Liu, Wen-wen; Gong, Qi; Wang, Tian-duan-yi; Tang, Yun; Zhu, Jin; Li, Jian; Zhang, Hai-yan; Mao, Fei; European Journal of Medicinal Chemistry; vol. 143; (2018); p. 33 – 47;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 6160-65-2, name is 1,1′-Thiocarbonyldiimidazole, 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 6160-65-2, Computed Properties of C7H6N4S

[00241] A solution of the amine (0.110 g, 0.43 mmol) in anhydrous CH2CI2 (2 ml_) was added dropwise over 2-5 minutes to an ice-salt bath cooled solution of 1 , 1′-thiocarbonyldiimidazole (95%, 0.162 g, 0.87 mmol, 2 eq.) in anhydrous CH2CI2 (6 ml_). After 15 minutes, the cooling bath was removed and the reaction mixture was stirred at room temperature for 1.5 hours after which time analysis by TLC (10% MeOH in CH2CI2) indicated complete consumption of the starting aniline. The mixture was cooled once again in an ice bath and 7 M NH3 in MeOH (620 mu, 4.3 mmol, 10 eq.) was added dropwise over 2-5 minutes. The bath was removed and the mixture was stirred over night at room temperature. Silica gel (~1 g) was added and the mixture was concentrated to dryness under reduce pressure. Flash column chromatography (RediSepRf Si02 (40 g), 100% CH2CI2? 10% MeOH in CH2CI2) gave the thiourea as an amber oil that solidified upon standing (0.130 g, 97%).

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, 1,1′-Thiocarbonyldiimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DUKE UNIVERSITY; LIEDTKE, Wolfgang; (189 pag.)WO2017/177200; (2017); 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. 26576-46-5, name is 5-Acetoacetlamino benzimdazolone, This compound has unique chemical properties. The synthetic route is as follows., Formula: C11H9N3O3

Synthesis of SYN-E; Formation of the dispersion synergist SYN-E was accomplished by diazotation of compound 7 and subsequent coupling with compound 3. [Show Image] 17.3 g (0.1 mol) of compound 7 in 300 mL water was dissolved by adding 10 mL (0.1 mol) of a 29% sodiumhydroxide-solution. 8.97 g (0.13 mol) of sodiumnitrite was added and the colourless solution was dropwise added to cooled concentrated hydrochloric acid (29.98 mL; 0.36 mol). The diazonium-salt was kept at a temperature between 0 and 5 C. After 15 minutes the excess of nitrite was neutralized by adding 3.0 g (0.03 mol) of sulfamic acid and a pH of 7 was obtained by adding 25.2 g (0.3 mol) of sodiumcarbonate. While the diazionium-salt was made, 23.3 g (0.1 mol) of compound 3 was dissolved in a mixture of 500 mL methanol and 10.0 mL (0.1 mol) 29 % sodiumhydroxide-solution. This solution was dropped into the diazonium-salt solution and a yellow suspension is immediately formed. The temperature was maintained between 0 and 5 C for about 3 hours and the yellow product was filtered and washed with methanol. The yield was 98 %.

According to the analysis of related databases, 26576-46-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Agfa Graphics N.V.; EP1790697; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 10040-96-7, 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. 10040-96-7, name is 1-(4-Bromophenyl)imidazole, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 21 (0.212 g, 1.12 mmol), CuI (20 mg, 0.112 mmol), (PPh3)2PdCl2 (40 mg, 0.056 mmol) and triethylamine (0.23 mL, 1.68 mmol) in acetonitrile (10 mL) was added 1-(4-bromophenyl)imidazole (0.5 g, 2.24 mmol). The reaction mixture was recharged with argon and stirred at 80 C for 3 h in a sealed tube. The mixture was extracted with ethyl acetate and the organic layer was washed successively with water and brine. The organic solvent was removed in vacuum. The residue was purified by column chromatography on silica gel (CH2Cl2/PE/NH3?H2O, 8:3:0.1) to afford 22c (0.3354 g, 1.01 mmol, 90.2%).HRMS (ESI) (M+H)+ m/z 332.1389, Calcd for C20H18N3O2 332.1394. 1H NMR (CDCl3, 400 MHz), delta: 7.93 (s, 1 H, H-imidazolyl), 7.55 (d, J = 8.1 Hz, 2 H, H-phenyl), 7.45-7.29 (m, 9 H, H-imidazolyl, H-phenyl), 5.25-5.15(m, 3 H, -NH-, -CH2-O-), 4.28 (s, 2 H, -NH-CH2-).

The chemical industry reduces the impact on the environment during synthesis 1-(4-Bromophenyl)imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Article; Li, Xue-Meng; Lv, Wei; Guo, Si-Yang; Li, Ya-Xin; Fan, Bing-Zhi; Cushman, Mark; Kong, Fan-Sheng; Zhang, Jun; Liang, Jian-Hua; European Journal of Medicinal Chemistry; vol. 171; (2019); p. 235 – 254;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem