Category: 57090-88-7

Electric Literature of 57090-88-7, A common heterocyclic compound, 57090-88-7, name is 1H-Imidazole-4-carbonitrile, molecular formula is C4H3N3, 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: A solution of 4-cyano-1H-imidazole (1000 mg, 10.74 mmol), 4-iodo -2-(trifluoromethyl)pyridine (3800 mg,14 mmol), (1R,2R)-N1,N2-dimethyl cyclohexane -1,2-diamine (150 mg, 1.07 mmol), CuI (200 mg, 1.07 mmol) and Cs2CO3 (7000 mg, 21.5 mmol) in 20 mL anhydrous DMF was stirred at 100 oC for 2 hours. The reaction mixture was cooled to room temperature and poured into 200 mL water. The mixture was extracted with ethyl acetate (80 mL*3). The organic layer were combined, washed by brine, dried by Na2SO4 and evaporated. The crude product was purified by silica flash column to afford compound 2 as white solid(1.5 g, 59percent yield).

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:
Article; Zheng, Qiangang; Chen, Ziqi; Wan, Huixin; Tang, Shuai; Ye, Yan; Xu, Yuan; Jiang, Lei; Ding, Jian; Geng, Meiyu; Huang, Min; Huang, Ying; Bioorganic and Medicinal Chemistry Letters; vol. 28; 23-24; (2018); p. 3808 – 3812;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 57090-88-7, These common heterocyclic compound, 57090-88-7, name is 1H-Imidazole-4-carbonitrile, 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 soluiton of 1H-imidazole-4-carbonitrile (300 mg, 3.2 mmol) in THF (50 mL) was added LiA1H4 (365 mg, 9.6 mmol). After stirred at reflux overnight, the reaction mixture was quenched by H20 (2 mL). And the mixture was dried over anhydrous Na2SO4 and filtered. The filtrate was evaporated in vacuum. The residue was used for next step without further purification.

Statistics shows that 1H-Imidazole-4-carbonitrile is playing an increasingly important role. we look forward to future research findings about 57090-88-7.

Reference:
Patent; SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE; GARDELL, Stephen; PINKERTON, Anthony B.; SERGIENKO, Eduard; SESSIONS, Hampton; (428 pag.)WO2018/132372; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 57090-88-7, name is 1H-Imidazole-4-carbonitrile, 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. category: imidazoles-derivatives

4-Cyanoimidazole (2.4 g, 25.9 mmol), KF-alumina (8 g), and iodomethane (15 mL, 240 mmol) were mixed and stirred at room temperature for 24 hours. After adding acetone (45 mL), it is stirred for 30 minutes and the solid is filtered off. After collecting the filtrate and blowing the solvent, the organic layer obtained by extraction with ethyl acetate and water is dehydrated with sodium sulfate, the solid is filtered off and the organic solvent is blown off. The reaction mixture was purified using silica gel column chromatography to obtain compound (3) (1.9 g, 17.7 mmol)This is obtained in 30% yield.

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

Reference:
Patent; Samsung Electronics Co., Ltd.; Cheil Industries Inc.; Pusan National University Institute for Research & Industry Cooperation; Noh Chang-ho; Yoon Ung-chan; Kwon O-hyeon; Choi Byeong-gi; (23 pag.)KR102046153; (2019); B1;,
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. 57090-88-7, name is 1H-Imidazole-4-carbonitrile belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 57090-88-7

A 22-L, four-neck, round-bottom flask equipped with a mechanical stirrer, a temperature probe, and an addition funnel with a nitrogen inlet was charged with IH- imidazole-4-carbonitrile (830 g, 8.91 mol, as prepared in the previous step), potassium carbonate (2.47 kg, 17.8 mol), and acetone (6.0 L). Agitation was initiated and the mixture was cooled to 10 0C with an ice bath. SEMCl (1.50 kg, 9.00 mol) was added through the addition funnel over 210 min to maintain the internal temperature below 15 0C. The reaction was then allowed to warm to ambient temperature and stirred at ambient temperature overnight (20 h). The reaction mixture was then cooled in an ice bath to 10 0C and quenched by the slow addition of water (8.0 L) over 30 min to maintain the internal temperature below 30 ¡ãC. The resulting mixture was transferred to a 22-L separatory funnel and extracted with ethyl acetate (2 x 7.0 L). The combined organics were concentrated under reduced pressure at 35 0C to give the crude product as a dark brown oil, EPO which was purified through a plug of silica gel (16.5 x 20 cm, 2.4 kg silica gel) using 2:1 heptane/ethyl acetate (15 L) as eluent. The fractions containing the product were combined and concentrated under reduced pressure at 35 0C to afford a mixture of the title compounds as a light brown oil [1785 g, 90percent). The 1H NMR spectrum was consistent with the assigned structure and indicated the presence of a 64:36 ratio of regioisomers.

The synthetic route of 57090-88-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2006/47277; (2006); A2;,
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. 57090-88-7, name is 1H-Imidazole-4-carbonitrile belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 1H-Imidazole-4-carbonitrile

To a solution of lH-Imidazole-4-carbonitrile (300 mg, 3.22 mmol) and 4-Fluoro- 3-methoxynitrobenzene (552 mg, 3.22 mmol) in DMF (Volume: 6446 mul) was added K2CO3 (891 mg, 6.45 mmol). The resulting mixture was brought to 120 0C and stirred overnight. The reaction mixture was diluted with EtOAc (20 mL), washed with water (2 x 10 mL), brine (10 mL), dried over MgSO4, filtered and concentrated in vacuo to give 1- (2-methoxy-4-nitrophenyl)-lH-imidazole-4-carbonitrile (698 mg, 2.86 mmol, 89 percent yield). LC-MS (M+H)+ = 245.0. IH NMR (500 MHz, MeOD) delta ppm 8.30 – 8.34 (1 H), 8.19 – 8.23 (1 H), 8.09 – 8.12 (1 H), 8.00 – 8.05 (1 H), 7.71 – 7.79 (1 H), 4.02 – 4.10 (3 H).

The synthetic route of 57090-88-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BOY, Kenneth M.; GUERNON, Jason M.; MACOR, John E.; OLSON, Richard E.; SHI, Jianliang; THOMPSON, III, Lorin A.; WU, Yong-Jin; XU, Li; ZHANG, Yunhui; ZUEV, Dmitry S.; WO2011/14535; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 57090-88-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 57090-88-7 name is 1H-Imidazole-4-carbonitrile, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: A solution of 4-cyano-1H-imidazole (1000 mg, 10.74 mmol), 4-iodo -2-(trifluoromethyl)pyridine (3800 mg,14 mmol), (1R,2R)-N1,N2-dimethyl cyclohexane -1,2-diamine (150 mg, 1.07 mmol), CuI (200 mg, 1.07 mmol) and Cs2CO3 (7000 mg, 21.5 mmol) in 20 mL anhydrous DMF was stirred at 100 oC for 2 hours. The reaction mixture was cooled to room temperature and poured into 200 mL water. The mixture was extracted with ethyl acetate (80 mL*3). The organic layer were combined, washed by brine, dried by Na2SO4 and evaporated. The crude product was purified by silica flash column to afford compound 2 as white solid(1.5 g, 59percent yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-Imidazole-4-carbonitrile, and friends who are interested can also refer to it.

Reference:
Article; Zheng, Qiangang; Chen, Ziqi; Wan, Huixin; Tang, Shuai; Ye, Yan; Xu, Yuan; Jiang, Lei; Ding, Jian; Geng, Meiyu; Huang, Min; Huang, Ying; Bioorganic and Medicinal Chemistry Letters; vol. 28; 23-24; (2018); p. 3808 – 3812;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 57090-88-7, A common heterocyclic compound, 57090-88-7, name is 1H-Imidazole-4-carbonitrile, molecular formula is C4H3N3, 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.

A flask charged with imidazole-4-carbonitrile (0.5 g, 5.2 mmol) {Synthesis, 677, 2003), 2-(trimethylsilyl)ethoxymethyl chloride (SEMCl) (0.95 mL, 5.3 mmol), K2CO3 EPO (1.40 g, 10.4 mmol), and acetone (5 mL) was stirred for 1O h at RT. The mixture was diluted with EtOAc (20 mL) and washed with water (20 mL) and brine (20 mL) and the organic layer dried over MgSO4. The crude product was eluted from a 20-g SPE cartridge (silica) with 30 percent EtOAc/hexane to give 0.80 g (70 percent) of the title compound as a colorless oil. Mass spectrum (CI (CH4), m/z) Calcd. for Ci0Hi7N3OSi, 224.1 (M+H), found 224.1.

The synthetic route of 57090-88-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2006/47277; (2006); A2;,
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. 57090-88-7, name is 1H-Imidazole-4-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C4H3N3

b) l-(2-Trimethylsilanyl-ethoxymethyl)-lH-imidazole-4-carbonitrile and 3-(2- trimethylsilanyl-ethoxymethyl)-3H-imidazole-4-carbonitrile; A 22-L, four-neck, round-bottom flask equipped with a mechanical stirrer, a temperature probe, and an addition funnel with a nitrogen inlet was charged with IH- imidazole-4-carbonitrile (830 g, 8.91 mol, as prepared in the previous step), potassium carbonate (2.47 kg, 17.8 mol), and acetone (6.0 L). Agitation was initiated and the mixture was cooled to 10 0C with an ice bath. SEMCl (1.50 kg, 9.00 mol) was added through the addition funnel over 210 min to maintain the internal temperature below 15 ¡ãC. The reaction was then allowed to warm to ambient temperature and stirred at ambient temperature overnight (20 h). The reaction mixture was then cooled in an ice bath to 10 ¡ãC and quenched by the slow addition of water (8.0 L) over 30 min to maintain the internal temperature below 30 ¡ãC. The resulting mixture was transferred to a 22-L separatory funnel and extracted with ethyl acetate (2 x 7.0 L). The combined organics were EPO concentrated under reduced pressure at 35 ¡ãC to give the crude product as a dark brown oil, which was purified through a plug of silica gel (16.5 x 20 cm, 2.4 kg silica gel) using 2:1 heptane/ethyl acetate (15 L) as eluent. The fractions containing the product were combined and concentrated under reduced pressure at 35 ¡ãC to afford a mixture of the title compounds as a light brown oil [1785 g, 90percent). The 1H NMR spectrum was consistent with the assigned structure and indicated the presence of a 64:36 ratio of regioisomers.

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 57090-88-7.

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2006/47504; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 57090-88-7, name is 1H-Imidazole-4-carbonitrile, molecular formula is C4H3N3, 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: 1H-Imidazole-4-carbonitrile

a) 1-(2-Trimethylsilanyl-ethoxymethyl)-1H-imidazole-4-carbonitrile A flask charged with imidazole-4-carbonitrile (0.50 g, 5.2 mmol) (Synthesis, 677, 2003), 2-(trimethylsilyl)ethoxymethyl chloride (SEMCl) (0.95 mL, 5.3 mmol), K2CO3 (1.40 g, 10.4 mmol), and acetone (5 mL) was stirred for 10 h at RT. The mixture was diluted with ethyl acetate (EtOAc) (20 mL) and washed with water (20 mL) and brine (20 mL) and the organic layer dried over MgSO4. The crude product was eluted from a 20-g SPE cartridge (silica) with 30percent EtOAc/hexane to give 0.80 g (70percent) of the title compound as a colorless oil: Mass spectrum (CI (CH4), m/z) Calcd. for C10H17N3OSi, 224.1 (M+H), found 224.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 57090-88-7, its application will become more common.

Reference:
Patent; Illig, Carl R.; Ballentine, Shelley K.; Chen, Jinsheng; DesJarlais, Renee Louise; Meegalla, Sanath K.; Wall, Mark; Wilson, Kenneth; US2007/249593; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 57090-88-7, name is 1H-Imidazole-4-carbonitrile, molecular formula is C4H3N3, 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. HPLC of Formula: C4H3N3

Example 4 Production of 1-(1H-imidazol-4-yl)-1-butanone A solution of 4-cyanoimidazole (2 g, 21.4 mmol) in THF (25 ml) was added dropwise to a solution (68.5 mL, 68.5 mmol, 3.2 equivalents) of 1 M n-propyl magnesium bromide in THF at 0to 10¡ãC under a nitrogen atmosphere. The mixture was stirred at 15 to 25¡ãC for 4 h. Water (20 ml) and 10percent aqueous sulfuric acid solution (45 ml) were successively added dropwise, and the mixture was stirred at 1 h. A 30percent aqueous sodium hydroxide solution was added dropwise to adjust the pH to 8. After partitioning, the aqueous layer was extracted with ethyl acetate (15 ml * 2). The organic layer was combined, and the mixture was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine, and concentrated under reduced pressure. The concentration residue was broken up with n-hexane (12 ml), and the crystals were collected by filtration and washed with n-hexane. The crystals were dried in vacuo (40¡ãC) to give 1-(1H-imidazol-4-yl)-1-butanone (2.45 g, yield 83percent). 1H-NMR (CDCl3): delta0.90(3H, t, J=7.4Hz), 1.60(2H, q, J=7.3Hz), 3.34(2H, q, J=7.1Hz), 7.77(1H, s), 7.85(1H, s)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 57090-88-7, its application will become more common.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1193258; (2002); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem