Tag: M.W=100-200

Electric Literature of 52099-72-6, A common heterocyclic compound, 52099-72-6, name is 1-(Prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one, molecular formula is C10H10N2O, 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.

EXAMPLE IX To a stirred solution of 8.5 parts of 1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one in 45 parts of N,N-dimethylformamide are added portionwise 1.7 parts of a sodium hydride dispersion 78%. After stirring for 1 hour at room temperature, the whole is cooled to 0-5 C and 8.65 parts of 1-bromo-3-chloropropane are added dropwise (slowly). Upon completion, stirring is continued for 3 hours at room temperature. The reaction mixture is poured into crushed ice and the product is extracted with methylbenzene. The extract is washed with water, dried, filtered and evaporated. The residue is crystallized from 2-propanol, yielding 5.5 parts (44%) of 1-(3-chloropropyl)-1,3-dihydro-3-(1-methylethenyl)2H-benzimidazol-2-one; mp. 115 C.

The synthetic route of 52099-72-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Pharmaceutica N.V.; US4066772; (1978); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 17289-19-9, These common heterocyclic compound, 17289-19-9, name is Methyl 1-methyl-1H-imidazole-4-carboxylate, 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 solution of Example 63a (1.40 g, 10.0 mmol) in CHC13 (30.0 mL) was added NBS (2.13g, 12.0 mmol). The reaction mixture was then stirred 18hrs at 50C and then cooled to room temperature. The residue was extracted with EtOAc (200 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 63b (500 mg, yield 22.8%). NMR (400 MHz, Chloroform- ) delta 7.60 (s, 1H), 3.91 (s, 3H), 3.67 (s, 3H).

The synthetic route of 17289-19-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FRONTHERA U.S. PHARMACEUTICALS LLC; JIN, Bohan; DONG, Qing; HUNG, Gene; (212 pag.)WO2017/218960; (2017); 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. 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, A new synthetic method of this compound is introduced below., Formula: C5H6N2O2

General procedure: Method B: Compounds 22 or 23 (1.2 mmol) and cesium carbonate (390 mg, 1.2 mmol) were dissolved in dry DMF (3 mL) under argon. After stirring of the mixture for 30 min at 50 C, a solution of the tosyl ester 12c or 12d (1 mmol) dissolved in dry DMF (3 mL) was added and the stirring was continued overnight at 50 C under argon. After evaporation of DMF in high vacuo, the residue was dissolved in EtOAc and the organic phase was washed with brine to neutral pH, dried over Na2SO4 and evaporated under reduced pressure. The residual product was purified by column chromatography (silica gel) using the appropriate solvent systems as it will be defined, in each case, below.

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

Reference:
Article; Moutevelis-Minakakis, Panagiota; Papavassilopoulou, Eleni; Michas, George; Georgikopoulou, Kalliopi; Ragoussi, Maria-Eleni; Neophytou, Niki; Zoumpoulakis, Panagiotis; Mavromoustakos, Thomas; Hadjipavlou-Litina, Dimitra; Bioorganic and Medicinal Chemistry; vol. 19; 9; (2011); p. 2888 – 2902;,
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. 3314-30-5, name is 1H-Benzo[d]imidazole-2-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., category: imidazoles-derivatives

Example 4 3-(1H-benzimidazol-2-methylene)-5-(cyclohexylaminosulfo)-2-indolone (Indo 4) 0.15 g (0.5 mmol) 5-(cyclohexylaminosulfo)-2-indolone and 0.10 g (0.685 mmol) 1H-benzimidazol-2-formaldehyde were suspended in 6 mL anhydrous ethanol, followed by addition of 2 drops of piperidine. The mixture was heated and refluxed in an oil bath for 30 min. A large quantity of yellow solid was precipitated, filtered, and washed with anhydrous ethanol, to obtain 0.17 g pale yellow solid, with a yield of 80.6percent. Analytical result by NMR spectroscopy: 1H-NMR (DMSO-d6) delta (ppm): delta13.86 (s, 1H), 11.68 (s, 1H), 8.35 (s, 1H), 8.08 (s, 1H), 7.76-7.84 (m, 3H), 7.48 (d, 1H, J=7.2 Hz), 7.66 (d, 1H, J=6.4 Hz), 7.38 (t, 1H), 7.31 (t, 1H), 7.10 (d, 1H, J=8.0 Hz), 3.02 (b, 1H), 1.60 (b, 5H), 1.50 (b, 5H). ESI-MS m/z: 421 [M-H]+ (100). Analysis showed that, the pale yellow solid is 3-(1H-benzimidazol-2-methylene)-5-(cyclohexylaminosulfo)-2-indolone, the structural formula of which is shown in Formula I, wherein R1 is cyclohexylaminosulfo, and R2 is hydrogen.

According to the analysis of related databases, 3314-30-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INSTITUTE OF RADIATION MEDICINE, CHINA ACADEMY OF MILITARY MEDICAL SCIENCES PLA; Yang, Xiaoming; Wang, Lin; Li, Changyan; Zhan, Yiqun; Liu, Jing; Luo, Teng; Yan, Haiyan; Zhang, Shouguo; Li, Wei; Wen, Xiaoxue; Peng, Tao; Li, Lu; (18 pag.)US2016/151334; (2016); 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

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