Author: Jessica.F

Electric Literature of 33529-02-1, These common heterocyclic compound, 33529-02-1, name is 1-Decyl-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.

General procedure: In a 250 mL two-neck round bottom flask equipped with a condenser linked to the vacuum-argon line, N-butylimidazole (title 99% w/w, Alfa Aesar) (4.2 g, 33.4 mmol) was charged and after degassing with three vacuum/argon cycles, 1H,1H,2H,2H-perfluorooctyliodide 96% w/w, Aldrich) (23.8 g, 50.1 mmol) was added. After three more vacuum/argon cycles the temperature of the oil bath was increased from 25 C to 120 C in 10 min. After heating for 6 h, NMR analysis of the crude reaction mixture (Fig. 6S, ESI) showed that the reaction went to completion and the occurrence, together with the target molecule C4-I, of the by-products N-butyl-imidazolium iodide and 1H,1H,2H-perfluoro-1-octene ( Scheme 1 ) typical of a Hofmann elimination of the imidazolium salts [29-31]. By cooling the presence of two phases was observed: a viscous red liquid (containing C4-I, N-butyl-imidazolium iodide and C6F13CH = CH2) at the top and a pale yellow liquid (the unreacted 1H,1H,2H,2H-perfluorooctyl iodide with C6F13CH = CH2) at the bottom. The phases were separated by decantation and the viscous red liquid washed three times with petroleum ether (3 * 50 mL) and three times with diethyl ether (3 * 50 mL). The solvent and the volatile by-product C6F13CH = CH2 (bp = 102-104) were eliminated under vacuum (30 C/53 Pa). After the work-up 1H NMR of the red oil showed peaks of C4-I (75%) and of N-butyl-imidazolium iodide (25%). The raw product (20 g) was dissolved in 20 mL of dichloromethane and filtered under argon on anhydrous celite (40 g) previously wetted with 200 mL of dichloromethane. The filtration was repeated two times. Celite was then washed with 80 mL of dichloromethane. Evaporation of the solvent (30 C/53 Pa) gives a red sticky wax with a yield of 75.1% (15.0 g, 25 mmol).

Statistics shows that 1-Decyl-1H-imidazole is playing an increasingly important role. we look forward to future research findings about 33529-02-1.

Reference:
Article; Zama, Isabella; Gorni, Giacomo; Borzatta, Valerio; Cassani, Maria Cristina; Crupi, Cristina; Di Marco, Gaetano; Journal of Molecular Liquids; vol. 223; (2016); p. 749 – 753;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 3034-38-6, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 3034-38-6, name is 5-Nitro-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

4-nitroimidazole(1.41 g), potassium carbonate (2.5 g), methyl iodide (1.9 g), and 20 mL of acetonitrile,The reaction was refluxed for 12 h. Spin dry under reduced pressure, add 50mL of water,It was extracted three times with 50 mL of ethyl acetate. The organic layers were combined and washed with saturated brine.The organic phase was dried by adding anhydrous Na2SO4, and dried under reduced pressure.1-methyl-4-nitroimidazole(1.5g).

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-Nitro-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; China Pharmaceutical University; Zhang Dayong; Zhang Tiantai; Shu Lei; (27 pag.)CN110330484; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 32673-41-9, name is 4-Imidazolemethanol hydrochloride, 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. Recommanded Product: 32673-41-9

Step A 1-Triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of 4-(hydroxymethyl)imidazole hydrochloride (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a solid which was sufficiently pure for use in the next step.

The synthetic route of 4-Imidazolemethanol hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US5852010; (1998); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 705-09-9,Some common heterocyclic compound, 705-09-9, name is 2-(Difluoromethyl)-1H-benzo[d]imidazole, molecular formula is C8H6F2N2, 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.

A mixture of 2-difluoromethyl-1H-benzimidazole (72.2 g) (67.0 g, 400 mmol), 2,4-dichloro-6-morpholino-1,3,5-triazine (94.0 g, 400 mmol) and anhydrous potassium carbonate (221.1 g, 1600 mmol) in DMF (1.60 L) was stirred at room temperature for 4 hours. The resulting mixture was poured into water. White precipitates were collected and washed with DMF and then acetone successively. The solid was dried under reduced pressure to give 4-chrolo-2-(2-difluoromethylbenzimidazol-1-yl)-6-morpholino-1,3,5-triazine (131.5 g, 358.6 mmol) as white crystal in 90% yield. MS m/z: 366 (M+) 1H-MNR(CDCl3) delta: 3.80-3.87 (4H, m), 3.94-4.01 (4H, m), 7.38-7.53 (2H, m), 7.58 (1H, t, J=54 Hz), 7.90 (1H, d, J=7 Hz), 8.42 (1H, d, J=7 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(Difluoromethyl)-1H-benzo[d]imidazole, its application will become more common.

Reference:
Patent; ZENYAKU KOGYO KABUSHIKI KAISHA; US2007/244110; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 96797-15-8, name is 4-Iodo-1-trityl-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. Product Details of 96797-15-8

Under nitrogen protection,Tetrakistriphenylphosphine palladium (2.0 g, 1.7 mmol, 0.074 eq), 4-iodo-1-trityl-1H-imidazole (0102-1) (10.0 g, 23.0 mmol, 1.0 eq),2-aldehyde phenylboronic acid (0103-1) (4.1 g, 27.5 mmol, 1.2 equiv) andTripotassium phosphate (12.0 g, 46 mmol, 2.0 equiv)Add to a mixture of 180 ml of dimethylformamide and water (5:1),Heat to 90C and react for 6 hours.Cool to room temperatureAfter suction filtration through Celite, the resulting filtrate was diluted with ethyl acetate to 1000 ml, washed with saturated brine three times, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by silica gel column chromatography (eluent: petroleum ether: ethyl acetate. Ester = 8:1 and petroleum ether: dichloromethane = 2:1),2-(1-trityl-1H-imidazol-4-yl)benzaldehyde (5.2 g, yield: 54%) was obtained as a white solid.

The synthetic route of 4-Iodo-1-trityl-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangzhou Bi Beite Pharmaceutical Co., Ltd.; Cai Xiong; Qian Changgeng; Weng Yunwo; Qing Yuanhui; Liu Bin; Lin Mingsheng; Wang Yanyan; (126 pag.)CN107383024; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 17325-26-7, name is 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 17325-26-7, Application In Synthesis of Methyl 1H-imidazole-5-carboxylate

Methyl 4-imidazolecarboxylate (1.09 g, 8.62 mmol) was slowly added to a suspension of sodium hydride (60% dispersion in oil, 0.52 g, 13 mmol) in DMF (40 mL). The mixture was heated to 80 C. and stirred at this temperature for 1 hour. A solution of compound 8 (3.61 g, 12.90 mmol) in DMF (20 mL) was added dropwise to the reaction mixture at this temperature and the reaction mixture stirred a further 12 hours at 80 C. The cooled mixture was filtered, the volatiles removed in vacuo and the residue purified by column chromatography on silica gel (100% n-heptane to 100% EtOAc) to yield compound 10 (0.91 g, 34%) as a yellow semi solid first LC-MS (MH+): m/z=311.3, tR (min,)=1.15 then compound 9 (1.38 g, yield: 51%) as a yellow solid LC-MS (MH+): m/z=311.3, tR (minutes)=1.16.

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; H. Lundbeck A/S; US2012/129836; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 6160-65-2,Some common heterocyclic compound, 6160-65-2, name is 1,1′-Thiocarbonyldiimidazole, molecular formula is C7H6N4S, 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.

Under the protection of argon, the cross spore alkali (1.86 g, 4.0 mmol) for 100 ml dichloromethane dissolved, at room temperature by adding 10 ml triethylamine andN,N’ – Sulfur carbonyl diimidazole (1.3 g, 8.0 mmol), the reaction overnight at room temperature. The reaction solution is poured into 100 ml ice water, dichloromethane extraction, anhydrous sodium sulfate after drying the organic phase concentration, silica gel column chromatography separation, dichloromethane: methanol=20:1 (v/v) elute and get the 3′ -N- (1 – Imidazole sulfur on behalf of the carboxamido) cross spore alkali 1.9 g, yield 82%,

The synthetic route of 6160-65-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guizhou Chinese Academy Of Sciences Natural Result Chemical Emphasis Experiment Shi (Guizhou Medical University Natural Result Chemical Emphasis Experiment Shi); Wang Liping; Zhu Weiming; Li Mingpeng; Xu Yanchao; Zuo Mingxing; (25 pag.)CN109879888; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 40644-16-4, name is 4-Bromo-1H-benzo[d]imidazol-2(3H)-one, 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: C7H5BrN2O

Step 3: To a solution of 4-bromo-1 ,3-dihydro-benzoimidazol-2-one (701 mg, 3.29 mmol) in DMSO (2 ml.) was added potassium acetate (803 g, 10.9 mmol), 1 ,1 ‘-bis(diphenyl phosphino)ferrocene palladium chloride (134 mg, 0.16 mmol) and bis(pinacolato)diboron (1.67 g, 6.58 mmol), and the reaction was degassed and heated in a microwave reactor for 30 minutes at 150 C. The reaction mixture was then filtered through a pad of Celite, water (60 ml.) was added, and the mixture was extracted with ethyl acetate (3 x 30 ml_). The combined organic extracts were dried over sodium sulfate, filtered, and then concentrated in- vacuo to give 4-(4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-1 ,3-dihydro-benzoimidazol-2- one, which was used in the next step without further purification.

The synthetic route of 4-Bromo-1H-benzo[d]imidazol-2(3H)-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WYETH; WO2009/108838; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 3034-38-6, 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 3034-38-6 as follows.

4-nitroimidazole (25 g, 221 mmol), sodium bicarbonate (37.1 g, 442 mmol) and water (600 mL) for dilution and then bromine (30 mL, 620 mmol) the temperature at the dropwise addition and the reaction mixture was at 40 C and reacted for 12 hours. After filtering the solids level of the reaction mixture was washed with toluene three times and dried under reduced pressure to give a yield of 2,5-dibromo-4-nitroimidazole of 39.8 g (67%). Prepared 2,5-di-bromo-4-nitroimidazole (39.8 g, 149 mmol) and water (450 mL) and then diluted to sodium iodide (223 g, 1486 mmol) was added and stirring under reflux was 12 sigan. Lower the temperature to room temperature, then filtered washing the solids in the reaction mixture with water, dried under reduced pressure to yield 2-bromo-5-iodo of 37.6 g (80%) was obtained a 4-nitroimidazole. Prepared 2-bromo-5-iodo-4- nitroimidazole (20 g, 63 mmol) in ethanol (190 mL) and then diluted in triethylamine (26.5 mL, 190 mmol) and platinum oxide (108 mg, 0.47 mmol) to give the applied wave after reacting for 3 hours under a hydrogen pressure of 3 bar in the reactor was concentrated under a reduced pressure after filtration with a silica gel and celite. Yield of the reaction mixture with 2-ethyl acetate 10% washed with hydrochloric acid solution to remove the moisture of the obtained organic layer over anhydrous magnesium sulfate, and then the filtrate was concentrated under reduced pressure and isopropyl alcohol and hexane, to obtain 7.9 g (65%) and then diluted with to give a-bromo-4-nitroimidazole.

According to the analysis of related databases, 3034-38-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Korea Research Institute of Chemical Technology; Kim, Phill Ho; Lee, Sang Ho; Kim, Soo Hyun; Lee, Ir Young; Yoon, Chang Soo; Oh, Tae Kwon; Cho, Sang Rae; (18 pag.)KR101650716; (2016); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 137049-00-4, 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 137049-00-4 as follows.

To a solution of 2-chloro-1-(1 /-/-indol-3-yl)-2-phenylethanone (0.200 g; 0.741 mmol) in DMF (5 mL) cooled to 0 C was added sodium hydride (60% dispersion in mineral oil; 0.053 g; 1.333 mmol). The reaction mixture was stirred at room temperature for 0.5 h. 1-Methyl-1 H- imidazole-4-sulfonyl chloride (0.268 g; 1.484 mmol) and DMAP (0.005 g; 0.037 mmol) were added and the reaction mixture was stirred at room temperature for 3 h. Water was added and the reaction mixture was extracted with ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification by flash chromatography on silica gel using a gradient of ethyl acetate (30% to 100%) in heptane furnished 0.301 g (98%) of 2-chloro-1-(1-((1-methyl-1 /-/-imidazol-4-yl)sulfonyl)-1 H-indol- 3-yl)-2-phenylethanone as a solid. ESI/APCI(+): 414 (M+H); 436 (M+Na). ESI/APCI(-): 412 (M- H).

According to the analysis of related databases, 137049-00-4, the application of this compound in the production field has become more and more popular.

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