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. 7098-07-9, name is 1-Ethyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C5H8N2

(1) in the equipped with a stirrer,thermometer,Calcium chloride drying tube and dropping funnel500 ml four-necked flask6.10 g (0.05 mol) of 1,3-propanesultone and150 mL of ethyl acetate was added and the mixture was stirred1,3-propane sultone dissolved,The flask was heated in an oil bath equipped with methyl silicone oil70 ° C,Slowly drop dissolved(0.065 mol) of N-ethylimidazole50 mL of ethyl acetate was added dropwise(Dropwise addition time: 30 min)Insulation reaction 2h,Pressure filtration,The residue was washed with ethyl acetate,Vacuum drying,To give 1- (3-sulfopropyl) -3-ethylimidazolium salt (EIm-PS)10.20 g,The yield was 93.6percent.

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 7098-07-9.

Reference:
Patent; Guangxi Kemao Forest Chemical Co., Ltd.; Jiangxi Jinan Forest Products Industrial Co., Ltd.; Guangdong Komo Co., Ltd.; Weng, Liang; Xu, Sheyang; Chen, Jiuji; (16 pag.)CN104926664; (2016); B;,
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. 492-98-8, name is 1H,1’H-2,2′-Biimidazole, This compound has unique chemical properties. The synthetic route is as follows., Formula: C6H6N4

Synthetic example 8:1 ,1 ‘-bis(4-(1 OH-phenothiazin-10-yl)phenyl)-1 H,1 ‘H^’-biimidazole8A mixture of 1H,1’H-2,2′-biimidazole (480 mg, 3.6 mmol), 10-(4-bromophenyl)-10H- phenothiazine (3.80 g, 10.8 mmol) and Cs2C03 (5.85 g, 18.0 mmol) in DMF (60 mL) was degassed (N2 bubbling, 15 min). CU2O (210 mg, 1.5 mmol) was added and the mixture was heated (140 C, 72h). The mixture was allowed to cool to room temperature and filtered through Celite washing with CH2CI2. The combined filtrate and washings were concentrated. The mixture was diluted with CH2CI2 and H2O and the organic phase was separated. The aqueous phase was re-extracted (CH2CI2) and the combined organics were washed (saturated aqueous NaCI), dried (MgS04), filtered and concentrated to give a solid residue. The residue was purified by flash chromatography (EtOAc/CH2CI2/MeOH 40:60:0 then 38:60:2 then 35:60:5) to give 1 ,1′-bis(4-(10H-phenothiazin-10-yl)phenyl)-1H,1’H-2,2,-biimidazole (1.12 g, 46%) as a colourless solid. A portion of this material was further purified firstly, by recrystallisation (CH2CI2/toluene/petrol) and then by distillation (sublimation apparatus 260 C, 10″6 mBar): m.p. 227 – 232 C (DSC); 1H NMR (CDCI3, 400 MHz) delta 6.36 – 6.42 (m, 4H), 6.86 – 6.97 (m, 12H), 7.08 – 7.16 (m, 8H), 7.20 (br s, 2H), 7.35 (br s, 2H); 13C NMR (CDCI3, 100 MHz) delta 118.4, 123.6, 123.8, 125.4, 126.8, 127.4, 128.4, 130.5, 135.2, 141.5, 143.3; HRMS (El) m/z 679.1710 C^Hzr^ [M – Hf requires 679.1733.

According to the analysis of related databases, 492-98-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; COMMONWEALTH SCIENTIFIC AND INDUSTRIAL RESEARCH ORGANISATION; MACDONALD, James Matthew; BOWN, Mark; UENO, Kazunori; WEBER, Karl Peter; O’CONNELL, Jenny Lee; HIRAI, Tadahiko; WO2012/51666; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 23328-88-3, 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 23328-88-3 as follows.

2-Bromo-1-(3,5-difluoro-2-nitrophenyl)-4-methyl-1H-imidazole A mixture of 1,3,5-trifluoro-2-nitrobenzene (2.2 mL, 18.6 mmol), 2-bromo-4-methylimidazole (3 g, 18.6 mmol) and K2CO3 (5.66 g, 41 mmol) in 80 mL DMF was stirred at room temperature overnight. The mixture was diluted with ethyl acetate and washed with water. Standard work up procedure followed by column purification using 10% ethyl acetate in dichloromethane as eluent provided 3.18 g (54% yield) of the product as a yellow powder. EIMS 317.9 [M+H]+.

According to the analysis of related databases, 23328-88-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELBION GMBH; WYETH; US2009/143367; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, molecular formula is C11H10F3N3, 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. Computed Properties of C11H10F3N3

Methyl 3-((tert-butoxycarbonyl)amino)-4-methylbenzoate (Intermediate A, 39.8 g, 0.15 mol, 1.5 eq.),3-(4-Methyl-1-1H-imidazole)-5-trifluoromethylaniline (starting material SM2, 24.1 g, 0.1 mol, 1.0 eq.) and N,N-dimethylformamide (250 ML).The reaction mixture was cooled to -10 to 0 C, and potassium t-butoxide (56.1 g, 0.5 mol, 5.0 eq.) was added to the reaction mixture and stirred for 2 to 3 hours.The reaction was monitored by high performance liquid chromatography, and water (100 mL) was added to the reaction mixture.A 3N aqueous hydrochloric acid solution was added to the system to adjust the pH to 7-8. filter,The filter cake is dried to give 2-methyl-5-((3-(4-methyl-1-1H-imidazole)-5-(trifluoromethylphenyl)carbamoylphenyl)carbamic acid tert-butyl 45.1 g of ester (intermediate B),A crude white to yellow solid with a purity of 94.8% and a molar yield of 95%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 641571-11-1, its application will become more common.

Reference:
Patent; Shanghai Fu Xingxing Tai Pharmaceutical Technology Co., Ltd.; Liu Xuejun; Chen Xiaodong; Hao Lu; Wu Feng; (23 pag.)CN109666023; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 152628-02-9,Some common heterocyclic compound, 152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, molecular formula is C19H20N4, 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.

Add 2-n-propyl-4-methyl-6-( -methylbenzimidazol-2′-yl) benzimidazole 100 g in 1000ml of acetone and of potassium hydroxide 22.0 g with stirring at 20-25C. Then of 4-bromomethyl-2′-cyanobiphenyl 92g is added at 20-25 C. Monitor the reaction on thin layer chromatography, after the reaction is completed, cooled to 0 to 5.0 C. and stirred for another hour at this temperature. The material is filtered, washed with chilled acetone, then wash with water, and then dried in a air drying cupboard at 80 C. Yield: 141.50 g (87.73% of theory); melting point: 196 C.-197 C; HPLC: 99.50%. N-3 isomer: 0.16%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, its application will become more common.

Reference:
Patent; INOGENT LABORATORIES PRIVATE LIMITED; RAY, Purna, Chandra; NIGAM, Satish; PANDEY, Anand, Kumar; PATIL, Premchand; REDDY, Jagan, Mohan; ORUGANTI, Nagaraju; WO2011/77444; (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. 934-22-5, name is 6-Aminobenzimidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 934-22-5

To the solution of 1H-benzimidazol-5-amine 121 (0.68 g, 5.11 mmol) in acetic acid (20 mL), the Compound 120a (1.06 g, 5.62 mmol) was added and stirred at room temperature for 20 minutes. TMSCN (1 mL) was added dropwise to the reaction mixture and continuously stirred for 2 hours. After reaction completing, the reaction mixture was concentrated under reduced pressure to yield a viscous liquid. The viscous liquid was diluted with ethyl acetate (10 mL) and water. The diluted solution was adjusted to the pH 6-7 with ammonia at an ice-bath. The neutralized solution was extracted with ethyl acetate (20 mL×4), dried over sodium sulfate, filtered and concentrated under reduced pressure to yield a viscous dark-yellow solid. The solid was dissolved in ethyl acetate (15 mL) and brine (15 mL). The mixture was stirred at room temperature for 2 minutes to form the pale-yellow precipitates. The pale-yellow precipitates was filtered and washed with water. The filtrate was dried over sodium sulfate and concentrated under reduced pressure to obtain the pale-yellow solid. Those pale-yellow solids were combined as the desired product 122a at a yield of 96%

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; National Health Research Institutes; Academia Sinica; Chen, Chih-Hao; Shih, Chuan; Chen, Chiung-Tong; Wang, Hwei-Jiung; Huang, Kai-Fa; US2020/71312; (2020); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 870837-18-6, These common heterocyclic compound, 870837-18-6, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, 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 THF (40 mL) solution of 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (4.00 g) obtained in Example 1, diethylphosphonoacetic acid ethyl ester (4.00 mL) and lithium hydroxide monohydrate (932 mg) were added one by one, and the reaction solution was agitated overnight at room temperature. 2N sodium hydroxide solution (30 mL) and ethanol (5 mL) were added to the reaction solution after confirming disappearance of the starting materials, and the reaction solution was agitated at room temperature overnight. The reaction solution was cooled to 0 C., 2N hydrochloric acid (30 mL) was added to the reaction solution, and the precipitation consequently deposited was separated by filtering with Kiriyama funnel. The obtained precipitation was washed with water and ethyl acetate, and 4.61 g of the title compound was obtained. The physical properties of the compound are as follows. 1H-NMR (DMSO-d6) delta (ppm): 7.81 (s, 1H), 7.60 (d, J=16 Hz, 1H), 7.56 (s, 1H), 7.39 (d, J=8.0 Hz, 1H), 7.35 (d, J=8.0 Hz, 1H), 7.16 (s, 1H), 6.66 (d, J=16 Hz, 1H), 3.88 (s, 3H), 2.15 (s, 3H).

The synthetic route of 870837-18-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eisai Co., Ltd.; US2006/4013; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

98873-55-3, name is 2-(1H-Imidazol-1-yl)acetonitrile, 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. Quality Control of 2-(1H-Imidazol-1-yl)acetonitrile

Reference Example 9 Using 0.88 g of 1-cyanomethylimidazole obtained in Reference Example 2, 1.309 g of 1-imidazolylthioacetamide hydrochloride was obtained by the same manner as described in

The synthetic route of 98873-55-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yamanouchi Pharmaceutical Co., Ltd.; US5565479; (1996); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 68282-53-1,Some common heterocyclic compound, 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, molecular formula is C5H6N2O, 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.

COMPOUND 14. 1.2 : NnN-DIETHYL-4- {6-METHOXY-2-r (5-METHYL-1H- IMIDAZOL-4-YL . METHYL]-7-PHENOXY-1. 2e3. 4- TETRAHYDROISOQUINOLIN-1-YL} BENZAMIDE; To INTERMEDIATE 10.2. 1 (30 mg, 0.06 mmol) was added a solution of hydrochloric acid in 1,4-dioxane (4N, 0.5 mL) at room temperature. The reaction mixture was stirred for an hour then concentrated by a stream of nitrogen and dried under vacuum. The residue was re-dissolved in 1,2-dichloroethane (1.5 mL) and to this solution was added 4-methyl-lH-imidazole-5-carbaldehyde (-2eq, 0.12 mmol, 12 mg) and followed by sodium triacetoxyborohydride (4eq, 0.24 mmol, 50 mg). The reaction mixture was stirred for 20 hr then quenched with saturated aqueous sodium bicarbonate and extracted to dichloromethane (15 mL x 2). Excess aldehyde was removed by stirring the extracted dichloromethane with polymer supported hydrazine for 2 hr. The polymer was filtered off and the filtrate was concentrated and dried under vacuum. Product was purified by flash chromatography, using Si02 column with MeOH/DCM (10: 90) afford 17.9 mg (0.034 mmol, 60%) of COMPOUND 14. 1.2 as light yellow oil. 1H NMR (500 MHz, CDC13): b 1. 05 (br s, 3H), 1.18 (br s, 3H), 2.00 (s, 3H), 2.50-2. 98 (br m, 4H), 3.10 (br s, 2H), 3.28 (m ; 1H), 3.49 (br s, 2H), 3.52 (m, 1H), 3.72 (s, 3H), 4.45 (s, 1H), 6. 28 (s, 1H), 6.65 (s, 1H), 6.68-7. 20 (m, 9H), 7.26 (m, 1H). 13C NMR (125 MHz, CDC13) : 6 10.97, 13.09, 14.42, 28. 70,39. 65, 43. 68, 46.96, 49.24, 56.20, 67. 66,106. 00,112. 63,115. 47,116. 47,122. 02,126. 57, 129.91, 130.26, 131.76, 132.93, 136.34, 142. 69,145. 32, 150.37, 150.37, 171. 51. (+) LRESIMS m/z 525 (M+H) +.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Methyl-1H-imidazole-4-carbaldehyde, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; WO2005/61484; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 17334-08-6, A common heterocyclic compound, 17334-08-6, name is (1-Methyl-1H-imidazol-2-yl)methanol, molecular formula is C5H8N2O, 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 1.12 g of 1-methyl-2-imidazolemethanol are added dropwise 1.8 ml of thionyl chloride at 0 C. After 18 hours at 20 C., the mixture is heated at 70 C. for 2 hours. The reaction medium is concentrated to give the expected product quantitatively. 1H NMR delta in ppm (DMSO d6): 3.90 (s, 3H); 5.22 (s, 2H); 5.36 (t, 1H); 7.77 (d, 1H); 7.80 (d, 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:
Patent; SANOFI-AVENTIS; US2007/185136; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem