Month: March 2021

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. 36947-68-9, name is 2-Isopropyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 36947-68-9

Example 47 Production of 2-[2-(2-Isopropylimidazol-1-yl)ethyl]isoindole-1,3-dione. N-(2-Bromoethyl)phthalimide (12.7 g, 50 mmol) and anhydrous potassium carbonate (6.9 g, 50 mmol) were added to a DMF (100 mL) solution of 2-isopropylimidazole (5.0 g, 45 mmol), and the mixture was stirred at 100C for 14 hours. The reaction mixture was poured into ice water, and extracted with ethyl acetate. An organic layer was dried over anhydrous sodium sulfate. Thereafter, the residue obtained by distilling off the solvents under a reduced pressure was purified with silica gel column chromatography (PSQ100B, chloroform : methanol = 100:1), to give the captioned compound (2.8 g, 22%) as an oily product. 1H-NMR (DMSO-d6) delta: 1.12 (d, J=6.7 Hz, 6H), 2.90-3.00 (m, 1H), 3.88 (t, J=6.3 Hz, 2H), 4.18 (t, J=6.3 Hz, 2H), 6.68 (s, 1H), 6.93 (s, 1H), 7.84-7.86 (m, 4H).

According to the analysis of related databases, 36947-68-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nippon Zoki Pharmaceutical Co., Ltd.; OOKUBO, Tomohiro; NAKAMURA, Ko; NAKAZAWA, Yoshitaka; NANBA, Hiroyoshi; YOSHIDA, Hiroyuki; EP2940003; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 10111-08-7, name is Imidazole-2-carboxaldehyde, molecular formula is C4H4N2O, 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: Imidazole-2-carboxaldehyde

Compound 234.1. lH-Imidazole-2-carbonitrile. Into a 1-L round-bottom flask, was placed a solution of lH-imidazole-2-carbaldehyde (5 g, 52.04 mmol) in NN- dimethylformamide (200 mL). Triethylamine (10.8 mL, 77.97 mmol), hydroxylamine hydrochloride (3.95 g, 56.84 mmol, 1.10 equiv), 1-propanephosphonic anhydride solution and 2,4,6-tripropyl-l,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide solution (T3P) (36.4 g, 114.40 mmol) were added to the reaction. The reaction mixture was stirred for 4h at 100 C, cooled and then quenched with 500 mL of water/ice. The aqueous phase was extracted with 3 x 1L of ethyl acetate, then the combined organic layers was washed with 2 x 1L of brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1/2) as eluent to furnish 2 g (41%) of the title compound as an off-white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 10111-08-7, its application will become more common.

Reference:
Patent; 3-V BIOSCIENCES, INC.; HEUER, Timothy Sean; OSLOB, Johan D.; MCDOWELL, Robert S.; JOHNSON, Russell; YANG, Hanbiao; EVANCHIK, Marc; ZAHARIA, Cristiana A.; CAI, Haiying; HU, Lily W.; WO2015/95767; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 15813-09-9, A common heterocyclic compound, 15813-09-9, name is 4,5-Diiodo-1H-imidazole, molecular formula is C3H2I2N2, 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 solution of 4,5-diiodoimidazole (35.5 g, 111.2 mmol) in anhydrous CH3CN (200 mL) at 0 C was added NaH (95%, 2.8 g, 111.2 mmol) portion wise. After the mixture was stirred for 30 min at rt, 10 (32 g, 101.1 mmol) was added portion wise at rt over a period of 1 h. After stirring at the same temperature for 18 h the reaction mixture was filtered over celite and washed with EtOAc (3 ¡Á 150 mL). The organic layer was concentrated under reduced pressure. The product was isolated by flash chromatography on silica gel using hexane/EtOAc (3:1) to give 11 as a pale yellow syrup. Yield: 57 g, 84%. 1H NMR (CDCl3, 400 MHz): delta 2.39 (s, 3H), 2.42 (s, 3H), 2.54 (ddd, 6.40 Hz, 7.80 Hz, 14.20 Hz, 1H), 2.80 (ddd, 2.32 Hz, 5.96 Hz, 14.24 Hz, 1H), 4.60 (m, 1H), 4.64 (d, 3.64 Hz, 2H), 5.63 (dt, 2.76 Hz, 6.4 Hz, 1H), 6.06 (dd, 5.48 Hz, 7.76 Hz, 1H), 7.22 (d, 8.24 Hz, 2H), 7.27 (d, 8.24 Hz, 2H), 7.84 (d, 8.24 Hz, 2H), 7.85 (s, 1H), 7.93 (d, 8.24 Hz, 2H);13C NMR (CDCl3, 100 MHz) delta 21.81, 21.87, 39.8, 63.8, 74.6, 79.8, 83.2, 89.5, 97.2, 126.3, 126.5, 129.4, 129.5, 129.6, 129.9, 138.9, 144.4, 144.7, 165.9, 166.2. HRMS (ESI): calcd for C24H23I2N2O5 (M+H)+ 672.9696, found 672.9693.

The synthetic route of 15813-09-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wauchope, Orrette R.; Johnson, Cameron; Krishnamoorthy, Pasupathy; Andrei, Graciela; Snoeck, Robert; Balzarini, Jan; Seley-Radtke, Katherine L.; Bioorganic and Medicinal Chemistry; vol. 20; 9; (2012); p. 3009 – 3015;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 71759-89-2, 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. 71759-89-2, name is 5-Iodo-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 4-iodoimidazole (50 g, 258 mmoles) in DMF (500 ml) was added triethyl amine (37.7 ml, 270.6 mmoles) and than triphenylmethyl chloride (69.7 g, 250 mmoles). After stirring at room temperature for 48 hours, the solution was poured into ice water (2.5 L). The solid was filtered and pumped on for several hours to yield the crude compound. Ethyl ether (200 ml) was added to the crude compound and the solution was filtered to yield 4-IODO-1-TRITYL-LH-IMIDAZOLE (104.1, 93%) as a white solid. ME (437)

The chemical industry reduces the impact on the environment during synthesis 5-Iodo-1H-imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CHIRON CORPORATION; WO2004/96822; (2004); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 89830-98-8, name is 5-Cyclopropyl-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: 89830-98-8

To a stirred solution of 9-(2H- 1 ,2,3-triazol-2-y)-3,4,7,8-tetrahydro-[1 ,4]diazepino[7,1-a]isoquinoine-2,5-dione (97 mg, 0.328 mmol) in 1 ,2-dichloroethane (3 mL) was added POCI3 (0.061 mL, 0.657 mmol) at rt and the resulting suspension was stirred at 100¡ãC for 35 min. The reaction mixture was cooled to rt and concentrated under reduced pressure to dryness. For complete removal of POCI3 the residue was taken up in toluene and the solvent was evaporated under reduced pressure. The residue was dried under high vacuo at rt. The resulting crude choro intermediate was dissolved in 1 ,2-dichloroethane (3 ml_), 4- cyclopropyl-1 H-imidazole (107 mg, 0.985 mmol) was added and the mixture was stirred at 100¡ãC for 2h. The reaction mixture was allowed to warm to rt and diluted with DCM. Saturated aqueous NaHC03 solution was added and the mixture was extracted twice with DCM. The combined organic layers were washed with brine, dried with sodium sulfate, filtered and the solvent was removed under reduced pressure. The crude product was purified by flash-column chromatography over silicagel (Biotage Isolera Four, eluent: pure DCM for 3 min, then from 0percent MeOH in DCM to 5percent MeOH in DCM in 14 min, 5percent MeOH in DCM for 3 min) to yield a yellow foam. Further purification by SFC (column: 2-Ethylpyridine 5 mutauiota, 250 x 30 mm, 60A, Princeton; eluent: 8percent MeOH/C02 for 1 min, then from 8percent MeOH/C02 to 13percent MeOH/C02 in 6 min ; flow 100 ml_ min ; U V detection at 220 n m) gave the title compound as slightly yellow foam (21 mg). UPLC-MS: MS 386.2 (M+hT); UPLC rt 0.86 min. 1H NMR (400 MHz, DMSO-d6) delta ppm 0.58 – 0.70 (m, 2 H), 0.74 – 0.82 (m, 2 H), 1.74 – 1.86 (m, 1 H), 2.91 (t, J=5.75 Hz, 2 H), 3.75 (t, J=5.&7 Hz, 2 H), 4.25 (s, 2 H), 7.22 (s, 1 H), 7.43 (s, 1 H), 7.54 – 7.63 (m, 1 H), 7.76 (d, J=8.80 Hz, 1 H), 8.10 (s, 1 H), 8.14 – 8.21 (m, 3 H).

The synthetic route of 5-Cyclopropyl-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; BEHNKE, Dirk; CARCACHE, David; ERTL, Peter; KOLLER, Manuel; ORAIN, David; WO2014/30128; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 10040-96-7, 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. 10040-96-7, name is 1-(4-Bromophenyl)imidazole, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of 4 (1.01 g, 1.22 mmol), CuI (23 mg, 0.12 mmol),PdCl2(PPh3)2 (45 mg, 0.064 mmol) and triethylamine (0.26 mL,1.86 mmol) in acetonitrile (10 mL), 2-amino-5-bromopyrimidine(635 mg, 3.65 mmol) were added. The reaction mixture wasrecharged with Ar and stirred at 80 C for 4 h in a sealed tube.The mixture was extracted with ethyl acetate and the organic layerwas washed with water and brine successively. The organic solventwas removed in vacuo. The residue was purified by column chromatography on silica gel (CH2Cl2/C2H5OH/NH3H2O, 10:0.6:0.1) toafford 20-OAc-3f (156 mg, 0.17 mmol, 13.9%).A solution of 20-OAc-3f (156 mg, 0.17 mmol) in MeOH (20 mL)was stirred at 65 C for 3H. The organic solvent was removed invacuo. The residue was purified by preparative TLC (petroleumether/acetone/triethylamine, 5:5:0.2) to yield analytically pureproduct 3f (14 mg, 0.015 mmol, 9.4%).

The chemical industry reduces the impact on the environment during synthesis 1-(4-Bromophenyl)imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Article; Han, Xu; Lv, Wei; Guo, Si-Yang; Cushman, Mark; Liang, Jian-Hua; Bioorganic and Medicinal Chemistry; vol. 23; 19; (2015); p. 6437 – 6453;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 4857-06-1, 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. 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step 1 60% Sodium hydride (1.42 g, 35.4 mmol) was added to mixture of 2-chlorobenzimidazole (5 g, 32.8 mmol) and DMF (50 mL) under ice-cooling, stirred at room temperature for 30 minutes, then added to 4-chlorobenzyl bromide (7.61 g, 37 mmol), and then stirred overnight at room temperature. The reaction mixture was added to saturated chloride ammonium aqueous solution (200 mL), and extracted with ethyl acetate (30 mL*3). The organic phase was washed by 1 mol/L hydrochloride (30 mL), saturated sodium hydrogen carbonate aqueous solution (30 mL), and saturated saline (30 mL), dried over anhydrous magnesium sulfate, and then concentrated in vacuo. The residue was purified by silica-gel column chromatography (ethyl acetate/hexane) to give 1-(4-chlorobenzyl)-2-chlorobenzimidazole (7.45 g, yield: 82%) as pale yellow solid. 1H-NMR (delta ppm TMS/CDCl3): 5.36 (2H, s), 7.11 (2H, d, J=8.2 Hz), 7.20-7.31 (5H, m), 7.72 (1H, d, J=7.8 Hz).

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, 2-Chloro-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shionogi & Co., Ltd.; KAI, Hiroyuki; TANAKA, Satoru; HIRAMATSU, Yoshiharu; NOZU, Azusa; NAKAMURA, Ken’ichioh; (260 pag.)US2016/24072; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 104619-51-4, name is Di(1H-imidazol-1-yl)methanimine, 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 104619-51-4, Quality Control of Di(1H-imidazol-1-yl)methanimine

Example 48: r4-(5-Amino- M.3,41 oxadiazot-2-yl>-5-fluoro-pyridin-3-v?-(2-fluoro-4- iodo-phenvD-amine; To a solution of 3-Fluoro-5- (2-fluoro-4-iodo-phenylamino)-isonicotinic acid hydrazide (100mg0.26mmol, 1eq) in DMSO (2mL) C- (Di-imidazol-i-yl)-methyleneamine (123mg, 0.77mmol, 3eq) was added. The reaction mixture was stirred at RT under argon overnight and then poured- into water. A solid precipitated out that was filtered out and washed with methanol to afford the desired product (65 mg). LC/MS (Method A) [5.19min; 416(M-H)]

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, Di(1H-imidazol-1-yl)methanimine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; APPLIED RESEARCH SYSTEMS ARS HOLDING N.V.; WO2007/123936; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 15813-09-9, The chemical industry reduces the impact on the environment during synthesis 15813-09-9, name is 4,5-Diiodo-1H-imidazole, I believe this compound will play a more active role in future production and life.

This compound was prepared following a literature procedure.23The mixture of 4,5-diiodo-1H-imidazole 20 (0.11 g, 0.34 mmol), (4-hydroxyphenyl)boronic acid (141 mg, 1.02 mmol), TBAB (11 mg,0.034 mmol), K2HPO4 (226 mg, 1.30 mmol) and Pd(PPh3)4 (25 mg,6 mol%) were transferred to a microwave reactor tube equipped with amagnetic stirring bar, followed by the addition of a mixture solvent ofMeOH/H2O (5 mL, 4:1), and the resulting mixture was degassed andback-filled with nitrogen and then stirred at 100 C (100 W) with microwaveirradiation for 60 min. After completion monitored by TLC, thereaction mixture was dissolved in aq. HCl (10%, 10 mL) and stirredvigorously. The mixture was washed with ethyl acetate (2 x 10 mL), thecombined aqueous layers were neutralised with sat. NaHCO3 (aq.) andextracted with ethyl acetate (3¡Á10 mL). The combined organic layerswere washed with H2O, dried over MgSO4 and concentrated in vacuo.The crude product was purified by flash chromatography (CH2Cl2:MeOH=50:1?10:1) to afford the product 4 as a white solid (30 mg,35%). Rf (CH2Cl2/MeOH 10:1): 0.25; 1H NMR (400 MHz, d6-DMSO): delta9.44 (2H, Br.s), 7.67 (1H, s), 7.25 (4H, d, J=8.4 Hz), 6.72 (4H, d,J=8.4 Hz); 13C NMR (100 MHz, d6-DMSO): delta 156.3, 134.4, 128.6,125.6, 124.3, 115.2. HRMS (ESI+) Calc. for C15H12N2O2 [M+Na]+275.0791, found 275.0794. HPLC: 97.7% (HPLC Method A), RT:13.3 min. The spectroscopic data matched that reported in the literature.

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, 4,5-Diiodo-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhou, Qingqing; Reekie, Tristan A.; Abbassi, Ramzi H.; Indurthi Venkata, Dinesh; Font, Josep S.; Ryan, Renae M.; Munoz, Lenka; Kassiou, Michael; Bioorganic and Medicinal Chemistry; vol. 26; 22; (2018); p. 5852 – 5869;,
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. 616-47-7, name is 1-Methyl-1H-imidazole, A new synthetic method of this compound is introduced below., name: 1-Methyl-1H-imidazole

General procedure: [BSTMG][HSO4]: 1,1,3,3-tetramethylguanidine (0.2 mol) and 1,4-butane sultone (0.2 mol) were charged into a 250 mL round bottom flask equipped with a reflux condenser. Then the mixtures were stirred at 353 K for 7 h. The obtained white solid zwitterion was washed several times with toluene to remove non-ionic residues and dried in vacuum. After that, a stoichiometric amount of sulphuric acid (0.2 mol) was added dropwise and the mixture was stirred for 10 h at 343 K. A kind of viscous ionic liquid phase was obtained and was washed by ether for several times. The ionic liquid was dried in vacuum for 2 h. The ionic liquids [BSTMG][CF3SO3], [BSTMG][CF3CO2], [BSPy][HSO4], [BSIMI][HSO4]and [BSEt3N][HSO4] were prepared by the same procedure.

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; Wu, Li; Li, Zhen; Wang, Fang; Lei, Min; Chen, Jing; Journal of Molecular Catalysis A: Chemical; vol. 379; (2013); p. 86 – 93;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem