Category: imidazoles-derivatives

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

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

Application of 705-09-9, These common heterocyclic compound, 705-09-9, name is 2-(Difluoromethyl)-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 67 (R)-2-(2-(difluoromethyl)-1H-benzo[d]imidazol-1-yl)-5-(4-(methylsulfonyl)benzyl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine A mixture of (R)-2-chloro-5-(4-(methylsulfonyl)benzyl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine (PREPARATION x10 50 mg, 0.127 mmol), 2-(difluoromethyl)-1H-benzo[d]imidazole (21.29 mg, 0.127 mmol), cesium carbonate (61.9 mg, 0.190 mmol), tris(dibenzylideneacetone)dipalladium(0) (4.64 mg, 5.06 mumol) and 2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl (4.83 mg, 10.13 mumol) in DMF 253 muL was heated to 130 C. in a microwave for 40 minutes. Additional tris(dibenzylideneacetone)dipalladium(0) (4.64 mg, 5.06 mumol) and 2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl (4.83 mg, 10.13 mumol) were added, and the reaction mixture was heated to 130 C. in a microwave for 1 hour. EtOAc and water were added and the mixture was filtered through Celite and extracted with EtOAc (2*). The combined extracts were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by column chromatography (SiO2-NH2, 30-100% EtOAc/hexane gradient) to afford the title compound as a yellow solid (14.3 mg, 21.4%). 1H NMR (400 MHz, CDCl3) delta 3.08 (s, 3H), 3.19-3.38 (m, 4H), 3.68 (td, J=12.00, 2.78 Hz, 1H), 3.83-3.92 (m, 1H), 3.94-4.02 (m, 1H), 4.11-4.20 (m, 1H), 4.44-4.63 (m, 3H), 7.36-7.75 (m, 6H), 7.93-8.01 (m, 3H), 8.17-8.23 (m, 1H). ESI-MS m/z [M+H]+ calc’d for C25H24F2N6O3S, 527.16. found 527.3.

The synthetic route of 705-09-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2012/220575; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

2849-93-6, name is 1H-Benzimidazole-2-carboxylic acid, 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. Recommanded Product: 1H-Benzimidazole-2-carboxylic acid

1 H-Benzimidazole-2-carboxylic acid (500 mg, 3.08 mmol) was suspended in EtOH (5 ml_), treated with thionyl chloride (1.12 ml_, 15.4 mmol), and heated to reflux overnight. The reaction mixture was concentrated in vacuo, yielding 644 mg (99%) of the crude product. 1H NMR (400 MHz, CD2CI2) delta 1.32 (t, 3H), 4.38 (q, 2H), 7.30 (m, 2H), 7.63 (m, 2H).

The synthetic route of 2849-93-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2006/49681; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 71759-87-0, 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. 71759-87-0, name is 4-Iodo-1-methyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

[0297] To a solution of 4-iodo-l -methyl- lH-imidazole (34.0 g, 163 mmol) in THF (300 mL) at -10 C was added isopropylmagnesium chloride (25.0 g, 244 mmol) dropwise under N2. The mixture was stirred for 1 h at this temperature, and then tributylchlorostannane (55.6 g, 171 mmol) was added drop-wise. The reaction was stirred at room temperature overnight under N2. The reaction mixture was diluted with saturated aqueous NH4Cl (400 mL) and extracted with EtOAc (200 mL x 3). The combined organic phases were washed with water (200 mL x 2) and brine (200 mL), dried over Na2S0, and concentrated to dryness, to afford the desired product (65.0 g, 100 %) as colourless oil, which was used in the next step directly. [0298] LC-MS (Agilent): Rt 2.84 min; m/z calculated for Ci6H32N2Sn [M+H] + 373.2, found 373.2

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

Reference:
Patent; EPIZYME, INC.; HARVEY, Darren Martin; CAMPBELL, John Emmerson; DUNCAN, Kenneth William; (246 pag.)WO2019/108824; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 32673-41-9, 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. 32673-41-9, name is 4-Imidazolemethanol hydrochloride, This compound has unique chemical properties. The synthetic route is as follows.

Step 8.a. 4-Hydroxymethyl-1-triphenylmethyl-imidazole 4-Hydroxymethylimidazole hydrochloride (compound xiii where R2 is H) (2.50 g, 18.6 mmol) and Et3N (2.59 ml, 18.6 mmol) were combined in DMF (30 ml) and stirred at room temperature.. A solution of chlorotriphenylmethane (5.19 g, 18.6 mmol) in DMF (25 ml) was added dropwise at room temperature and the resulting mixture was stirred at room temperature for about 23 hours and then poured into ice water (300 ml).. The product was filtered off, washed with cold water (75 ml) and triturated with p-dioxane (30 ml).. The product was filtered off and dried under reduced pressure to yield product (4.96 g, 78%). NMR (300MHZ, DMSO-d6, 30C) 7.3-7.5 (9H, m), 7.25-7.35 (1H, d), 7.0-7.2 (6H, m), 6.7-6.75 (1H, s), 4.15-4.2 (2H, m).

The chemical industry reduces the impact on the environment during synthesis 4-Imidazolemethanol hydrochloride. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SOCIETE DE CONSEILS DE RECHERCHES ET D’APPLICATIONS SCIENTIFIQUES (S.C.R.A.S.); EP1382607; (2004); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 98873-55-3,Some common heterocyclic compound, 98873-55-3, name is 2-(1H-Imidazol-1-yl)acetonitrile, molecular formula is C5H5N3, 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 potassium hydroxide (0.25 g, 4.5 mmol) in 3 ml of dimethylsulfoxide was purged with argon and cooled to 10C. A solution of 2-imidazol-1-ylacetonitrile (13, 0.23 g, 2.2 mmol) and carbon disulfide (0.32 g, 4.3mmol) in 2 ml of dimethylsulfoxide was then slowly added. The cooling bath was removed and the resulting orange mixture was stirred for 15 min at room temperature. A solution of [2-(2,4-dichlorophenyl)-3-methylsulfonyloxy-propyl]methanesulfonate (25, 0.54 g, 1.4 mmol) in 2 ml of dimethylsulfoxide was then added dropwise. The reaction mixture was stirred for 1 h at room temperature and then poured on water. The phases were separated, the aqueous phase was extracted with dichloromethane, the combined organic layer was washed with water and brine, dried over sodium sulfate and evaporated under reduced pressure.The remainder was purified by chromatography on silica gel, using ethyl acetate/ heptane 1 : 1 as eluent system to deliver 2-[5-(2,4-dichlorophenyl)-1,3-dithian-2-ylidene]-2-imidazol-1-yl-acetonitrile (26, 0.49 g, 1.3 mmol, 92 %) as an inseparable 1 : 1 mixture of the E- and Z-isomer. 1H-NMR (400 MHz, CDCl3): delta= 3.12 (dd, 1H, J = 7.1, 14.1 Hz), 3.18 (dd, 1H, J = 6.8, 14.1 Hz), 3.31 (dd, 1H, J= 6.8, 14.1 Hz), 3.49 (dd, 1H, J = 7.1, 14.1 Hz), 4.10 (q, 1H, J = 7.1 Hz), 7.02 (t,1H, J = 1.3 Hz), 7.17 (s, 1H), 7.29 (dd, 1H, J = 2.2, 8.4 Hz), 7.44 (d, 1H, J = 2.2Hz), 7.48 (d, 1H, J = 8.4 Hz), 7.59 (s, 1H). LC-MS: Rt = 0.97 min; MS: m/z = 368[M+1]+.

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

Reference:
Article; Gagnepain, Julien; Jeanmart, Stephane; Bonvalot, Damien; Jacob, Olivier; Lamberth, Clemens; Synlett; vol. 30; 1; (2019); p. 59 – 62;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1632-83-3, The chemical industry reduces the impact on the environment during synthesis 1632-83-3, name is 1-Methylbenzimidazole, I believe this compound will play a more active role in future production and life.

General procedure: 4.3 General procedure for CuO-catalyzed arylation and alkenylation of 1,3-azole (0012) Under argon, 0.5mmol of the bromobenzene or bromoalkene was added to the reaction mixture containing 0.25mmol of the benzoxazole, 0.5mmol K2CO3, 0.025mmol CuO, and 0.075mmol PPh3, followed by the addition of 2mL dry diglyme. The sealed reaction tube was stirred at 160C for 5-24h. After cooling, the reaction mixture was centrifuged to remove solid and separated the organic phase. Then, organic phase was extracted and dried over anhydrous MgSO4, and concentrated under reduced pressure after filtered. The residue was purified by column chromatography on silica gel eluted to afford corresponding product.

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, 1-Methylbenzimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhang, Wu; Tian, Yujie; Zhao, Na; Wang, Yuanyuan; Li, Jia; Wang, Zhenghua; Tetrahedron; vol. 70; 36; (2014); p. 6120 – 6126;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 2735-62-8,Some common heterocyclic compound, 2735-62-8, name is 2-(1-Methyl-1H-benzo[d]imidazol-2-yl)acetonitrile, molecular formula is C10H9N3, 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-(1-Methyl-1H-benzo[d]imidazol-2-yl)acetonitrile (171 mg, 1.0 mmol), t-BuOK (112 mg, 1.0 mmol), and dry THF (5 mL) were stirred for 30 min at room temperature. To the resulting mixture 3-(phenylethynyl)quinoxaline-2-carbonitrile 1a (128 mg, 0.5 mmol) was added by portions. The reaction mixture was stirred for 48 h at room temperature and then evaporated to dryness without heating. The residue was treated with some drops of acetic acid. After evaporation it was mixed with silica gel and purified by flash column chromatography on silica gel (2.5¡Á40 cm) with CHCl3 as the eluent. The first fraction recovered was 1a (32 mg, 25%). The orange fraction was collected and purified additionally by flash column chromatography on Al2O3 (2.5¡Á20 cm) with CHCl3 as the eluent. The orange red fraction with Rf 0.65 gave 5e (48 mg, 24%).

The synthetic route of 2735-62-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nguyen, Huong T.L.; Gulevskaya, Anna V.; Pozharskii, Alexander F.; Nelina-Nemtseva, Julia I.; Tetrahedron; vol. 70; 31; (2014); p. 4617 – 4625;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 37148-86-0, name is 4-(4-(Trifluoromethyl)phenyl)-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. SDS of cas: 37148-86-0

Sodium hydride (60% in oil) (32 mg) was added at 0 C. to a DMF (6.7 mL) solution of Reference Example 2 (0.17 g), and the mixture was stirred at 0 C. for 30 minutes. 2-Fluoro-4- (trifluoromethyl) benzonitrile (0.13 g) was added to the reaction solution at 0 C., and the mixture was stirred at room temperature for 3 hours. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with a saturated saline solution and dried over sodium sulfate. After evaporation of the solvent of the organic layer after drying under reduced pressure, the obtained residue was purified by silica gel chromatography (elution solvent; hexane: ethyl acetate) to obtain Reference Example 5 (0.18 g).

The synthetic route of 4-(4-(Trifluoromethyl)phenyl)-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUMITOMO DAINIPPON PHARMA COMPANY LIMITED; ISOBE, YOSHIAKI; BAN, HITOSHI; SAITO, YASUHIRO; WATANABE, HITOSHI; (44 pag.)JP2018/135270; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem