Category: imidazoles-derivatives

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. 7152-24-1, name is 2-(Methylthio)benzimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: imidazoles-derivatives

General procedure: A sealable reaction tube equipped with a magnetic stirrer barwas charged with 5,6-dimethyl-1H-benzo[d]imidazole (0.50 mmol,73 mg), benzaldehyde (1.0 mmol, 106 mg), di-tert-butyl-peroxide(1.0 mmol, 146 mg), 4 A molecular sieves (50 mg) and ethyl acetate(3.0 mL). The rubber septum was then replaced by a Teflon-coatedscrew cap, then the reaction must be under N2 and the reactionvessel placed in an oil bath at 110 C. After stirring the mixture atthis temperature for 15 h, it was cooled to room temperature anddiluted with ethyl acetate then washed with 0.5 mmol/L NaOHaqueous solution (5.0 mL3), dried over by MgSO4. After the solventwas removed under reduced pressure, the residue was purifiedby column chromatography on silica gel (hexane/EtOAc, 4:1 to6:1) to afford the desired product (5,6-dimethyl-1H-benzo[d]imidazol-1-yl)(phenyl)methanone (3a, 116 mg, 93% yield).

The synthetic route of 7152-24-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yu, Lin; Wang, Min; Wang, Lei; Tetrahedron; vol. 70; 35; (2014); p. 5391 – 5397;,
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, Recommanded Product: Methyl 1H-imidazole-5-carboxylate

To a solution of 97 (3.00 g, 23.8 mmol) in DMF (5 mL) was added NaH (1.14 g, 28.6 mmol) in portions at 0 C. The mixture was stirred at 0 C for 1 h. Then SEM-CI (8.44 mL, 47.6 mmol) was added drop-wise at 0 C. The reaction mixture was stirred at 25 C for 13 h. The reaction was quenched by sat. aq. NH4CI (10 mL) at 0 C and then extracted with EtOAc (20 mL x 3). The combinedorganic phase was washed with brine (20 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (petroleum ether/ethyl acetate = 1:2) to give 98 (2.00 g, yield 33%) as a yellow oil. 1H NMR (400 MHz, CDCI3) 7.73 (s, 1H), 7.62 (s, 1H), 5.31 (s, 2H), 3.91 (s, 3H), 3.50 (t, J = 8.0 Hz, 2H), 0.92 (t, J = 8.0 Hz, 2H), -0.01 (s, 9H). To a solution of 98 (2.00 g, 7.80 mmol) in THF (20 mL) was added LiAIH4 (355 mg, 9.36 mmol) in portions at 0 C. Themixture was stirred at 25 C for 3 h. The reaction was quenched by sat. aq. potassium sodium tartrate (1 mL) at 0 C, filtered and concentrated in vacuo to give 99 (1.4 g, yield 79%) as a colorless oil. 1HNMR (400 MHz, CDCI3) 7.56 (s, 1H), 6.99 (s, 1H), 5.23 (s, 2H), 4.61 (s, 2H), 3.48 (t, J = 8.0 Hz, 2H),0.91 (t, J = 8.0 Hz, 2H), 0.01 (s, 9H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 1H-imidazole-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ANACOR PHARMACEUTICALS, INC.; AKAMA, Tsutomu; CARTER, David Scott; HALLADAY, Jason S.; JACOBS, Robert T.; LIU, Yang; PLATTNER, Jacob J.; ZHANG, Yong-Kang; WITTY, Michael John; (149 pag.)WO2017/195069; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 4856-97-7,Some common heterocyclic compound, 4856-97-7, name is (1H-Benzoimidazol-2-yl)methanol, molecular formula is C8H8N2O, 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.

The resulting solid (1H-benzimidazol-2-yl) methanol (34 mmol) was dissolved in 250 mL of dichloromethane and stirredFollowed by addition of manganese dioxide (0.68 mmol). The temperature was raised to 40 C and stirring was continued for 2 hours to monitor the reaction. After the reaction is complete, the product is evaporated to drynessDichloromethane, 150 mL of tetrahydrofuran was added. Directly to the next step

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

Reference:
Patent; Shenyang Pharmaceutical University; Zhao Linxiang; Liu Dan; Li Kun; Ma Tianyi; Jing Yongkui; (13 pag.)CN107118249; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 219814-29-6, name is 2,5-Dibromo-4-methylimidazole, molecular formula is C4H4Br2N2, 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 C4H4Br2N2

[0304] To a solution of 18-1 (3.6 g, 15 mmol) and K2C03 (4.1 g, 30 mmol) in DMF ( 18 mL) was added iodomethane ( 1 .4 mL, 23 mmol) at 25C. The solution was stirred for 1 5 h. The mixture was poured into water and extracted with EA The combined organic phase was dried over anhydrous Na?S04, and the residue was purified by chromatography on silica gel (EA/hexane) to giv e 18-2 (1 .6 g, 41 %). NMR (400 MHz, CDC13): delta 3.52 (s. 3H). 2.21 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 219814-29-6, its application will become more common.

Reference:
Patent; ALIOS BIOPHARMA, INC.; WANG, Guangyi; BEIGELMAN, Leonid; TRUONG, Anh; NAPOLITANO, Carmela; ANDREOTTI, Daniele; HE, Haiying; STEIN, Karin, Ann; WO2015/26792; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 32673-41-9, name is 4-Imidazolemethanol hydrochloride belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C4H7ClN2O

(a) Triphenylmethyl chloride (2.78 g) was added to 4-hydroxymethylimidazole hydrochloride (1.34 g) and triethylamine (2.8 ml) in dichloromethane (20 ml) stirred at 0 C. under an atmosphere of argon. The mixture was stirred for 18 hours and the insoluble solid was collected by filtration. The solid was washed well with water and dried under high vacuum to give 4-hydroxymethyl-1-triphenylmethyl-imidazole (B) as a white solid (2.4 g); NMR (90 MHz, d6 -DMSO): 4.3 (d, 2H), 4.8 (br t, 1H), 6.7 (S, 1H), 7.0-7.5 (complex m, 16H).

The synthetic route of 32673-41-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Imperial Chemical Industries plc; US5091425; (1992); 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. 36947-68-9, name is 2-Isopropyl-1H-imidazole, A new synthetic method of this compound is introduced below., Safety of 2-Isopropyl-1H-imidazole

General procedure: Using the synthetic procedure of 2-phenyl-1H-imidazole-5-carbaldehyde (17j) as an example. 2-Phenyl-1H-imidazole (2.8 g, 19.42 mmol) was added to a suspension of 60% NaH (2.33 g, 58.26 mmol) in DMF 20 ml at 0 deg. C and the mixture was stirred for 0.5 h. Then N,N-dimethylsulfamoylchloride (3.34 g, 23.3 mmol) were added dropwise and the reaction mixture was stirred for 2 h at room temperature. Saturated NH4Cl solution was added and the resulting mixture as extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated under vacuum.The residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1:4) as eluent to furnish (2.4 g,49.2%) of the title compound as a dark yellow solid. 1H NMR(400 MHz, CDCl3) d: 7.72e7.66 (m, 2H), 7.48e7.40 (m, 4H), 7.10 (d,J 1.6 Hz, 1H), 2.48 (s, 6H). 13C NMR (126 MHz, CDCl3) d: 147.63,130.39, 130.12, 129.87, 127.94, 127.74, 122.08, 37.52. In a 250 ml three neck round-bottomed flask, which was purged and maintained with an inert atmosphere of nitrogen, was placed a solution of N,N-dimethyl-2-phenyl-1H-imidazole-1-sulfonamide(2.3 g, 9.16 mmol) in THF 30 ml. This was followed by the addition of n-butyllithium (4.4 mL, 10.99 mmol) dropwise at -78 deg.C over a period of 30 min. To this mixture was added DMF (4.58 mL,59.54 mmol). The resulting solution was stirred at -50 deg. C for30 min, then hydrogen chloride (23 mL, 22.9 mmol, 1M) was added.The reaction mixture was stirred for 2 h at room temperature.The pH of the solution was adjusted to 7-8 with saturated sodium bicarbonate solution. The resulting solution was extracted with 3 x15 ml of ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was purified by silica gel chromatography (ethyl acetate/petroleum ether =1:4) to furnish the title compound (1.37 g, 87.3%) as yellow solid. Total yield: 43.0%. 1H NMR(400 MHz, CDCl3) d: 11.34 (s, 1H), 9.76 (s, 1H), 8.02 (s, 2H), 7.93 (s,1H), 7.46 (s, 3H). LC/MS (ESI) m/z: [M 1] calcd for C10H8N2O,173.06; found, 173.1. Other imidazolecarbaldehydes were prepared as described in the procedure for synthesizing 17j.

The synthetic route of 36947-68-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Dong, Jianghong; Chen, Shengwei; Li, Runfeng; Cui, Wei; Jiang, Haiming; Ling, Yixia; Yang, Zifeng; Hu, Wenhui; European Journal of Medicinal Chemistry; vol. 108; (2016); p. 605 – 615;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 103057-10-9, 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 103057-10-9 as follows.

EXAMPLE 1 STR49 To a solution of diisopropylamine (1.078 mL) in anhydrous THF (7 mL) was added n-butyllithium (3.08 mL; 2.5M) dropwise at 0 C. The resulting solution was stirred at 0 C. for 40 minutes and then was cooled to -23 C. To this mixture was added N-methyl-2-piperidinone (0.80 mL) (1), the mixture was stirred at -23 C. for 0.5 hour, and then at -78 C. for 1 hour. To the above mixture was added dropwise a solution of 4-chloromethyl-N-trityl-imidazole (2.70 g) STR50 in anhydrous THF (14 mL). The mixture was stirred at -78 C. for 4 hours and then was allowed to warm up to room temperature slowly overnight (16 hours). Water and ethyl acetate were added to the mixture, the resulting mixture was shaken vigorously, the layers separated, and the aqueous layer was extracted with ethyl acetate several times. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated to give the crude product, which was purified by flash chromatography (1% to 2% of ammonia saturated methanol in CH2 Cl2) to give 2 (1.58 g; 52% yield).

According to the analysis of related databases, 103057-10-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Schering Corporation; US5932596; (1999); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1849-01-0, name is 1-Methyl-1H-benzo[d]imidazol-2(3H)-one, 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. Product Details of 1849-01-0

EXAMPLE V A mixture of 25 parts of 1,3-dihydro-1-methyl-2H-benzimidazol-2-one, 64 parts of sodium methanolate solution 30% and 240 parts of methanol is stirred for one hour at room temperature. Then there are added 27.88 parts of 3-(chloromethyl)pyridine hydrochloride and stirring is continued for 3 hours at reflux temperature. The reaction mixture is cooled and the formed precipitate (sodium chloride) is filtered off. The filtrate is evaporated. The residue is crystallized from a mixture of 4-methyl-2-pentanone and 2,2′-oxybispropane. The product is filtered off and dried, yielding 16 parts (39.3%) of 1,3-dihydro-1-methyl-3-(3-pyridinylmethyl)-2H-benzimidazol-2-one; mp. 90 C.

The synthetic route of 1849-01-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Pharmaceutica N.V.; US4181802; (1980); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 150058-27-8, 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. 150058-27-8, name is Methyl 2-ethoxy-1H-benzo[d]imidazole-7-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

60 g of 2-ethoxy-1H-benzimidazole-7-carboxylic acid methyl ester and 500 ml of ethanol were added to the clean reaction flask, Stirred at room temperature for 10 minutes, 75.5 g of potassium carbonate was added, 60.3g 3-(4′-(bromomethyl)-[1,1′-biphenyl]-2-yl)-1,2,4-oxadiazol-5(4H)-one , and 4.8 g of tetrabutylammonium bromide, heated to reflux 10h, the ethanol was evaporated to dryness under reduced pressure, and the mixture was stirred for half an hour in 1800 ml of water, 120ml water washing, filter to dry, solid with 400ml ethanol temperature reflux solution dissolved, cooling to 0-5 , 2 hours of crystallization temperature.Filtered, washed with 20 ml of ethanol, suction filtered to dryness, in 50 to 60 vacuum drying, 2-ethoxy-1-((2′-(2,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)benzimidazole-7-carboxylic acid methyl ester was obtained 66.8 g, yield: 78.0percent, purity: 98.9percent)

The synthetic route of Methyl 2-ethoxy-1H-benzo[d]imidazole-7-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chongqing Langtian Pharmacy Co., Ltd.; Meng, Wenxue; Long, Daobing; Sun, Wenjing; (11 pag.)CN105669495; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 1467-16-9, name is 1H-Imidazole 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. COA of Formula: C3H5ClN2

A mixture of lithium(1+) ion 3-amino-7-chloro-5/-/-pyrrolo[2,3- 5]pyrazine-2-carboxylate, Intermediate 15 (190 mg, 0.869 mmol), CDI (21 1 g, 1.30 mmol) and 1 /-/-imidazole hydrochloride (1 :1) (100 mg, 0.956 mmol) in DMF (4 ml) was stirred at RT for 0.5 h. Additional CDI (50 mg, 0.31 mmol) was added and the reaction was left to stir at RT for a further 0.5 h. The reaction mixture was diluted with water (6 ml) then left to stir at RT for 20 min. The resulting suspension was filtered then the collected solid was washed with water then dried under vacuum to afford the product as a yellow/orange solid (164 mg, 72%). 1 H NMR (500 MHz, DMSO-cfe) delta 11.98 (s, 1 H), 8.80 (s, 1 H), 7.99 (t, J (s, 1 H), 7.58 (s, 2H), 7.12 (dd, J = 1.5, 0.8 Hz, 1 H). LC/MS (System A): m/z (ESI+) = 263 [MH+], Rt = 0.82 min, ELS purity = 100%.

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

Reference:
Patent; ENTERPRISE THERAPEUTICS LIMITED; MCCARTHY, Clive; HARGRAVE, Jonathan, David; HAY, Duncan, Alexander; SCHOFIELD, Thomas, Beauregard; WENT, Naomi; (261 pag.)WO2018/96325; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem