Tag: M.W=100-200

Application of 50995-95-4,Some common heterocyclic compound, 50995-95-4, name is 2-Propylimidazole, molecular formula is C6H10N2, 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 vessel with a magnetic stirrer bar was charged with imidazole derivative (0.5 mmol), CuI (10 mg, 0.05 mmol), Cs2CO3 (0.33 g, 1 mmol), PPh3 (26 mg, 0.1 mmol) and tetrabutylammonium bromide (TBAB) (0.2 g, 0.6 mmol) under a nitrogen atmosphere. The reaction vessel was evacuated and backfilled with nitrogen three times. In a separate flask, a solution of dry dioxane (2 mL) containing the 1,1-dihalo-1-alkenes (1 mmol) was evacuated and back-filled with nitrogen gas three times. The dioxane solution was then added to the reaction flask via a syringe and the reaction mixture heated to 100 C for 30 hours. The reaction mixture was cooled to room temperature, quenched with 5 mL of a saturated NH4Cl solution, and extracted with ethyl acetate (3 x 10 mL). The combined organic phases were dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by flash column chromatography with ethyl acetate (EA) and petroleum ether (Pet) as the eluent to afford the corresponding products:

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

Reference:
Article; Wang, Man-Gang; Yu, Hua; Wu, Jun; Shang, Zhi-Cai; Journal of Chemical Research; vol. 37; 9; (2013); p. 570 – 573;,
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. 52099-72-6, name is 1-(Prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one, A new synthetic method of this compound is introduced below., category: imidazoles-derivatives

Step A: Ethyl 2,3-dihydro-3-(1-methyl-ethenyl)-2-oxo-1H-benzimidazol-1-butanoate A solution of 19 g of 1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one [described in J. Chem. Soc. Perkins, 1982, p. 261] in 150 ml of dimethylformamide was added with stirring at 20 C.+-2 C. to 5.75 g of sodium hydride as a 50% suspension in oil and 10 ml of dimethylformamide and the mixture was stirred for another 30 minutes. 23.4 g of ethyl 4-bromo-butyrate were added to the mixture over 15 minutes and the mixture was stirred at room temperature for 4 hours and was poured into 800 ml of iced water. The mixture was extracted with ether and the organic phase was washed with water, dried and evaporated to dryness under reduced pressure to obtain 33 g of ethyl 2,3-dihydro-3-(1-methyl-ethenyl)-2-oxo-1H-benzimidazol-1-butanoate.

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; Roussel Uclaf; US4585770; (1986); A;,
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. 1457-58-5, name is 2-Methyl-1H-imidazole-5-carboxylic acid, A new synthetic method of this compound is introduced below., Quality Control of 2-Methyl-1H-imidazole-5-carboxylic acid

WSC (4.0 g), HOBt (3.2 g) and triethylamine (3.8 mL) were added to a solution of benzyl 4-aminopiperidine-1-carboxylate (3.3 g) and 2-methyl-1H-imidazole-4-carboxylic acid (2.0 g) in acetonitrile (50 mL) and stirred for 12 hours. The reaction solution was concentrated and the residue was dissolved in chloroform and an aqueous saturated sodium bicarbonate solution. A chloroform layer was separated, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified with silica gel column chromatography to obtain the title compound (2.4 g, 49%) as colorless powder. NMR (300 MHz, CDCl3) delta: 1.41-1.56 (2H, m), 1.93-2.06 (3H, m), 2.40 (3H, s), 2.92-3.07 (2H, m), 4.06-4.21 (2H, m), 5.14 (2H, s), 7.07 (1H, d, J = 8.3), 7.30-7.42 (5H, m), 10.92 (1H, br)

The synthetic route of 1457-58-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1564213; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 2302-25-2,Some common heterocyclic compound, 2302-25-2, name is 4-Bromo-1H-imidazole, molecular formula is C3H3BrN2, 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.

-Bromo- lH-imidazole(3.2 g, 21.8 mmol) was weighed into a 500 mL round bottomed flask equipped with a magnetic stir bar under a nitrogen atmosphere. Anhydrous DMF, (12 mL) was added and the mixture was placed on ice. After 10 min the mixture was treated with NaH (0.840 g, 21.0 mmol. 60% dispersion in oil). After 5 min, the ice bath was removed and the reaction was warmed to room temperature. After 15 min of vigorous stirring the ice bath was replaced and 3-(4-cyanophenyl)oxaziridine-2-carboxylic acid tert-butyl ester (1.92 g, 7.80 mmol) was added. The reaction was vigorously stirred for 5 min and the ice bath was removed. After 5 min the mixture was diluted with saturated NaHCC>3 and extracted with EtOAc. The organics were washed with dilute sodium carbonate, dried over Na2SC>4, filtered, and concentrated. The residue was purified using silica gel chromatography (0-5% MeOH / DCM) to afford the title compound (1.16 g, 4.43 mmol, 57 %) as a yellow oil: ]H NMR (400 MHz, CDCI3) delta 9.22 (s, 1H), 7.36 (d, / = 1.5 Hz, 1H), 6.97 (d, / = 1.5 Hz, 1H), 1.48 (s, 9H); ESIMS m/z 262 ([M]+), 260 ([M-2]”).

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

Reference:
Patent; DOW AGROSCIENCES LLC; GARIZI, Negar; TRULLINGER, Tony K.; HUNTER, Ricky; ZHANG, Yu; NIYAZ, Noormohamed M.; KNUEPPEL, Daniel; LOWE, Christian T.; BUYSSE, Ann M.; WO2013/62980; (2013); 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. 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: Methyl 1H-imidazole-5-carboxylate

To a stirred solution of methyl 4-imidazolecarboxylate (CAS Number 17325-26-7; 0.500 g,3.97 mmol) and 1,10-phenanthroline (1.400 g, 7.94 mmol) in DMSO (5 ml) was added iodobenzene(1.600 g, 7.94 mmol), Cs2CO3 (3.800 g, 11.9 mmol) and Cu20 (0.567 g, 3.97 mmol) at rt in a microwave tube. The reaction mixture was heated at 100C for 15 mm in microwave. The resulting reaction mixture was cooled to rt and filtered. The obtained filtrate was diluted with water (60 ml) and extracted with EtOAc (3 x 60 ml). The combined organic layer was dried over Na2SO4, filtered andconcentrated under reduced pressure yielding methyl 1 -phenyl- 1H-imidazole-4-carboxylate (0.450 g,2.23 mmol). This material was directly used for next step without any further purification. LCMS:Method C, 2.066 mi MS: ES+ 203.00.

According to the analysis of related databases, 17325-26-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MISSION THERAPEUTICS LIMITED; KEMP, Mark Ian; STOCKLEY, Martin Lee; MADIN, Andrew; (95 pag.)WO2017/103614; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 570-22-9, These common heterocyclic compound, 570-22-9, name is 1H-Imidazole-4,5-dicarboxylic acid, 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.

In H2O (12ml) solvent, was added CuBr (0.121g, 0.85mmol), 2,2′- bipyridine (0.086g, 0.5mmol), 4,5-imidazole acid (0.078g, 0.5mmol), NaOH (0.020 g, 0.5mmol), placed on a magnetic stirrer was stirred for 30 minutes, the reaction was placed in 25ml teflon-lined autoclave, sealed in a high temperature oven, constant-temperature 160 C for five days to 5 C / h rate down to room temperature, a blue precipitate in the reactor bulk crystal, in 60% yield (based on copper).

Statistics shows that 1H-Imidazole-4,5-dicarboxylic acid is playing an increasingly important role. we look forward to future research findings about 570-22-9.

Reference:
Patent; Capital Normal University; Lu, Xiaoming; Cheng, Yifeng; (14 pag.)CN103965224; (2016); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 3752-24-7, These common heterocyclic compound, 3752-24-7, name is 4,5,6,7-Tetrahydro-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.

EXAMPLE 14 1-[1-(4-Chloro-3-methyl-phenyl)-1H-imidazol-4-yl-methyl]-4,5,6,7-tetrahydro-1H-benzoimidazole-, Hydrochloride (1:2) [1-(4-Chloro-3-methyl-phenyl)-1H-imidazol-4-yl]-methanol was treated first with thionylchloride, then with the reaction mixture of sodium hydride and 4,5,6,7-tetrahydro-benzimidazole. After extractive workup and chromatography the title compound was obtained as the free base. It was converted into its white hydrochloride salt. Mp.>250 C. (MeOH/Et2O), MS: m/e=326 (M+).

Statistics shows that 4,5,6,7-Tetrahydro-1H-benzo[d]imidazole is playing an increasingly important role. we look forward to future research findings about 3752-24-7.

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

Electric Literature of 3012-80-4, 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 3012-80-4 as follows.

A solution of 1-methyl-2-formylbenzimidazole (1 g) in methanol (27 mL) and acetic acid (0.54 mL) was treated with aminoacetaldehyde diethylacetal (0.9 g, 1 equivalent) and NaCNBH3 (0.85 g, 2 equivalents) at 25° C., stirred for 1 hour. The mixture was partitioned between water and ethyl acetate. The organic layer was separated, washed sequentially with saturated NaHCO3 and brine, and concentrated. The residue was chromatographed on silica gel, eluting with 8percent methanol/dichloromethane to give 1.2 g (64percent) of the title compound.

According to the analysis of related databases, 3012-80-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Flentge, Charles A.; Chen, Hui-Ju; DeGoey, David A.; Flosi, William J.; Grampovnik, David J.; Huang, Peggy P.; Kempf, Dale J.; Klein, Larry L.; Krueger, Allan C.; Madigan, Darold L.; Randolph, John T.; Sun, Minghua; Yeung, Ming C.; Zhao, Chen; US2005/131042; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 60-56-0, 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. 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, This compound has unique chemical properties. The synthetic route is as follows.

Step 4: {2-[4-(1-Methyl-imidazol-2-ylsulfanylmethyl)-benzoylamino]-phenyl}-carbamic acid tert-butyl ester (Compound 138) To a solution of N-methyl-2-mercaptoimidazole (28 mg, 0.25 mmol) in THF (1 mL), at r.t. under N2 atmosphere were successively added 137 (70 mg, 0.20 mmol), triphenylphosphine (70 mg, 0.27 mmol) followed by dropwise addition of diethyl azodicarboxylate (48 muL, 0.31 mmol). The mixture was stirred for 2 h and the solvent was removed in vacuo. Purification by flash chromatography using MeOH/CHCl3 (5:95) as the eluent afforded the title compound 138 (81 mg), in 91% yield, which was found to contain some diethyl hydrazodicarboxylate residus. The compound was used as is without further purification.

The chemical industry reduces the impact on the environment during synthesis 1-Methyl-1H-imidazole-2(3H)-thione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MethylGene, Inc.; US6897220; (2005); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 2034-23-3, name is 5-Chloro-1H-benzo[d]imidazol-2(3H)-one, 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 2034-23-3, Application In Synthesis of 5-Chloro-1H-benzo[d]imidazol-2(3H)-one

Step 1. A mixture of 5-chloro-lH-benzo[d]imidazol-2(3H)-one (200 mg, 1.19 mmol), cesium carbonate (850 mg, 2.61 mmol) and tert-butyl 2-bromoacetate (0.37 mL, 2.5 mmol) in acetone (10 mL) was sealed and heated in an oil bath at 65 C for 6 h. The reaction mixture was filtered and concentrated in vacuo, taken up into DCM (20 mL), washed with 5% citric acid and brine, dried over MgSCn, filtered and concentrated in vacuo. The residual solid was recrystallized from 2: 1 hexanes-EtOAc (10 mL) to afford di-tert-butyl 2,2′-(5-chloro2-oxo-lH-benzo[d]imidazole-l,3(2H)-diyl)diacetate (160 mg) as a white solid. LC-MS retention time = 1.38 min; m/z = 285.1 [M-2(t-Bu)+H]+. (Column: Waters Aquity BEH C18 2.1 X 50 mm 1.7^m-particles; Solvent A = 100% Water/ 0.05% TFA; Solvent B = 100% Acetonitrile/0.05% TFA; Flow Rate = 0.8 mL/min. Start % B = 2; Final % B = 98; Gradient Time = 1.5 minutes; Wavelength = 220 nm).

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, 5-Chloro-1H-benzo[d]imidazol-2(3H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VIIV HEALTHCARE (No.5) LIMITED; BENDER, John A.; LOPEZ, Omar D.; NGUYEN, Van N.; YANG, Zhong; WANG, Alan Xiangdong; WANG, Gan; MEANWELL, Nicholas A.; BENO, Brett R.; FRIDELL, Robert A.; BELEMA, Makonen; THANGATHIRUPATHY, Srinivasan; (350 pag.)WO2016/172425; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem