Month: May 2021

These common heterocyclic compound, 3718-04-5, name is 5-Vinyl-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. Computed Properties of C5H6N2

Example 20 (E)-2-(4-fluorophenyl)- 1 -methyl- 1 -(4-(2-(l -methyl- 1 H-imidazol-4-yl)vinyl)phenyl)- 1.2.3.4- tetrahvdroisoquinolin-6-ol and (EN)-2-(4-fluorophenvn-l-methyl-l-(4-(2-(l -methyl-lH-imidazol- 5-yl)vinyl)phenyl)-1.2.3.4-tetrahvdroisoquinolin-6-ol To a 30 mL vial, 4-vinyl-lH-imidazole (357 mg, 3.79 mmol) was dissolved in tetrahydrofuran (2 mL) and the solution was cooled to 0C. Sodium hydride (60% dispersion in mineral oil, 152 mg, 3.79 mmol) was added and the mixture was stirred for 10 min at 0C. The reaction mixture was charged with iodomethane (237 mu^, 3.79 mmol) and stirred overnight at room temperature. The reaction was quenched with saturated ammonium chloride (15 mL) and dichloromethane (25 mL) was added. The organic phase was collected, passed through a phase separator and concentrated to give crude product. Crude material was purified by silica gel chromatography (0-20% methanol/dichloromethane) to afford a mixture of 1 -methyl -4-vinyl-lH- imidazole and l-methyl-5 -vinyl- lH-imidazole (290 mg, 71% yield) as a yellow oil. NMR (400 MHz, CHLOROFORM-^ delta 3.51 (s, 3 H), 3.49 (s, 3 H), 4.97 (dd, J=11.12, 1.52 Hz, 1 H), 5.09 (dd, J=11.12, 1.01 Hz, 1 H), 5.44 (dd, J=17.68, 1.01 Hz, 1 H), 5.67 (dd, J=17.43, 1.77 Hz, 1 H), 6.25 – 6.49 (m, 2 H), 6.62 – 6.73 (m, 1 H), 7.04 (s, 1 H), 7.25 (d, J=7.58 Hz, 2 H).

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

Reference:
Patent; NOVARTIS AG; BURKS, Heather Elizabeth; KARKI, Rajeshri Ganesh; KIRBY, Christina Ann; NUNEZ, Jill; PEUKERT, Stefan; SPRINGER, Clayton; SUN, Yingchuan; THOMSEN, Noel Marie-france; WO2015/92634; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 38585-62-5, 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. 38585-62-5, name is (4-Methyl-1H-imidazol-5-yl)methanol hydrochloride belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 7 2,3,4,5-Tetrahydro-5-methyl-2-[(5-methyl-1H-imidazol-4-yl)methyl]-1H-pyrido[4,3-b]indol-1-one A mixture of 2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one (49.97 g), p-toluenesulphonic acid monohydrate (9.50 g) and 4-hydroxymethyl-5-methylimidazole hydrochloride (20.25 g) in N-methylpyrrolidinone (250 ml) was stirred and heated to 125 (over 1 h) The reaction was then heated at 125-130 for 4.5 h, during which time two further portions of 4-hydroxymethyl-5-methylimidazole hydrochloride (17.51 g and 6.88 g) were added. The reaction mixture was cooled, diluted with water (100 ml), and the stirred mixture was treated slowly with 8% aqueous sodium bicarbonate (750 ml). The resultant suspension was stirred in an ice bath for 1 h and then filtered to give a solid (57.64 g). A portion of this solid (11.09 g) was dissolved in dichloromethane (307 ml) and ethanol (166 ml), boiled with decolourising charcoal for 10 min and then filtered. The dichloromethane was distilled off at atmospheric pressure until the temperature of the mixture was at 65. The stirred mixture was cooled and the resulting precipitate was filtered off to give the title compound (9.28 g), t.l.c. (System A, 50:8:1) Rf 0.55.

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-Methyl-1H-imidazol-5-yl)methanol hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Glaxo Group Limited; US5196534; (1993); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 67014-36-2, These common heterocyclic compound, 67014-36-2, name is 5-Amino-6-methyl-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.

8.1 g of 5-amino-6-methylbenzimidazolone-(2) was stirred with 250 ml of water and 14.5 ml of 31.5% hydrochloric acid for 1 hour and then diazotized at 0 C. after the addition of ice, by adding an aqueous sodium nitrite solution. EXAMPLE 2 8.1 g of 5-amino-6-methylbenzimidazolone-(2) was diazotized with sodium nitrite solution in the same method as described in Example 1.

The synthetic route of 67014-36-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dominion Colour Corporation; US6706864; (2004); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 72459-45-1,Some common heterocyclic compound, 72459-45-1, name is 1-(2-Bromobenzyl)-1H-imidazole, molecular formula is C10H9BrN2, 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.

1- (2-Bromo-benzyl) -1H-imidazole (20 g, 84.0 mmol),Palladium acetate (500 mg),Triphenylphosphine (500 mg),Potassium carbonate (23 g, 167 mmol) was dissolved in DMSO (200 mL)The mixture was heated to 140 C under nitrogen for 2 hours.LC-MS showed the reaction was complete,The reaction solution was concentrated to dryness,The residue was dissolved in ethyl acetate (200 mL)Water (2 × 100 mL),Saturated brine (50 mL).Organic phase filtration,concentrate.The residue obtained 5H- imidazo [5,1-a] isoindole (10.0 g) was purified by flash silica gel column.

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

Reference:
Patent; Shanghai Hansen Bio-pharmaceutical Technology Co., Ltd.; Jiangsu Haosen Pharmaceutical Group Co., Ltd.; Tong Chaolong; Bao Rudi; Li Yuannian; (67 pag.)CN107312005; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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 19213-72-0 as follows. SDS of cas: 19213-72-0

SYNTHESIS EXAMPLE 9 Synthesis of 4(5)-Chloro-5(4)-phenylimidazole-2-carboxylic acid (Compound No. 15) 2.5 g of 4(5)-chloro-2-(ethoxycarbonyl)-5(4)-phenylimidazole (Compound No. 5) was added to 50 ml of a 5% aqueous sodium hydroxide solution, and the mixture was reacted at the reflux temperature for one hour to obtain a reaction mixture including sodium 4(5)-chloro-5(4)-phenylimidazole-2-carboxylate. The reaction mixture was poured into ice water and neutralized with hydrochloric acid. A precipitated crystal was separated by filtration and washed with water to obtain 4(5)-chloro-5(4)-phenylimidazole-2-carboxylic acid (Compound No. 15) having a melting point of 158 to 160 C.

According to the analysis of related databases, 19213-72-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ishihara Sangyo Kaisha Ltd.; US5023336; (1991); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 253453-91-7, 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. 253453-91-7 name is 2-Chloro-1-methyl-1H-imidazole, 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.

Example 53[0208] A 1.6 M solution of n-butyllithium in hexanes (2.27 ml, 3.6 mmol) was added dropwise to a solution of 2-chloro-l -methyl- lH-imidazole* (0.4 g, 3.45 mmol) in anhydrous TEtaF (10 ml) at – 78 C. The reaction mixture was maintained below -78 C during the addition. After 15 min, a solution of 2-chloro-6-methylphenyl isocyanate (0.64 g, 3.79 mmol) in TEtaF (5 ml) was added and the solution was stirred at -78 C for further 2h. The solution was quenched by the addition of aq NH4Cl and partitioned between EtOAc and water. The organic layer was separated and washed with brine, dried and concentrated. The crude product was purified on silica gel chromatography by using 30% EtOAc/Hexane, to give compound 53 as white solid (353 mg, 36% yield). 1H NMR (500 Hz, DMSO-d6) delta 9.96(s, IH), 7.82 (s, IH), 7.40 (dd, J= 1.7, 5.74 Hz, IH), 7.27 (m, 2H), 3.83 (s, 3H,), 2.23 (s, 3H); ESI-MS: calcd for (C12H11C12N3O) 282, found 282 (M-H+). HPLC: retention time: 17.83 min.; purity: 96%

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-1-methyl-1H-imidazole, and friends who are interested can also refer to it.

Reference:
Patent; ABRAXIS BIOSCIENCE, LLC; TAO, Chunlin; WANG, Qinwei; NALLAN, Laxman; POLAT, Tulay; KORONIAK, Lukasz; DESAI, Neil; WO2010/144338; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 89088-69-7, A common heterocyclic compound, 89088-69-7, name is 1-Methyl-1H-imidazol-4-amine hydrochloride, molecular formula is C4H8ClN3, 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 solution of 1 -methyl- lH-imidazol-4-amine hydrochloride (Intermediate 36 , 16.39 g, 122.74 mmol) and 2,4-dichloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-J]pyrimidine (Intermediate 9, 21 g, 61.37 mmol) and DIPEA (42.9 ml, 245.47 mmol) in ethanol (264 ml) were heated at 88 0C overnight. The reaction mixture was cooled to 0 0C and filtered to provide 2-chloro-N-(l -methyl- lEta-imidazol-4-yl)-7-tosyl-7Eta-pyrrolo[2,3-d]pyrimidin-4-amine contaminated with DIPEA. The solid was dissolved in EtOAc (400 ml) and the solution was washed with water (3×100 ml). During the process, the title product crashed out of solution and collected through filtration. Concentration of the mother liquor provided additional title product (total=18.8 g, 76%). LCMS: 403 [M+H]+.1H NMR (300 MHz, DMSO-J6) deltappm 10.75 (br. s., 1 H), 7.96 (d, 2 H), 7.63 (d, 1 H),7.40 – 7.55 (m, 3 H), 7.35 (s, 1 H), 7.23 (br. s., 1 H), 3.68 (s, 3 H), 2.37 (s, 3 H)

The synthetic route of 89088-69-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; CHUAQUI, Claudio, Edmundo; HUANG, Shan; IOANNIDIS, Stephanos; SHI, Jie; SU, Mei; SU, Qibin; WO2010/38060; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 109012-23-9, name is Ethyl 1-methyl-4-nitro-1H-imidazole-2-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 109012-23-9, Application In Synthesis of Ethyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate

Ethyl 1-methyl-4-nitroimidazole-2-carboxylate17 (6, 613 mg, 3.1 mmol) was hydrogenated over 5% palladium on charcoal in ethanol. The resulting amino compound was dried thoroughly under vacuum to remove traces of ethanol. It was then dissolved in dichloromethane (20.0 mL) and the solution was cooled to 0-5 C. To the cold solution was added triethylamine (0.5 mL, 3.7 mmol) followed by benzoyl chloride (0.4 mL, 3.4 mmol). The reaction mixture was allowed to attain room temperature and then stirred for 12 h. Upon completion, the reaction was quenched with water (15.0 mL) and stirred for 15 min. The organic layer was separated and aqueous layer was washed with dichloromethane (2 × 10 mL). Combined organic layers were dried over sodium sulfate and evaporated to obtain a yellow oil. The crude product was purified by column chromatography using silica gel and 2% methanol in chloroform as the eluent system to obtain 7 as a yellow solid (808 mg, 96%).

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:
Article; Satam, Vijay; Babu, Balaji; Chavda, Sameer; Savagian, Mia; Sjoholm, Robert; Tzou, Samuel; Liu, Yang; Kiakos, Konstantinos; Lin, Shicai; David Wilson; Hartley, John A.; Lee, Moses; Bioorganic and Medicinal Chemistry; vol. 20; 2; (2012); p. 693 – 701;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 106848-38-8, 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. 106848-38-8, name is 1-Benzyl-4-bromo-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: PdCl2(dppf), PdCl2(tbpf) and (A.caPhos)PdCl2. A mixture of the halogenated heterocycle (0.66 mmol) in anhydrous THF (13.2 mL) was degassed by bubbling argon for few minutes. Then, PdCl2(dppf) (27.0 mg, 0.033 mmol, 5.0 mol%), TMEDA (0.130 g, 1.12 mmol, 1.7 equiv) and finally NaBH4 (42.4 mg, 1.12 mmol, 1.7 equiv) were introduced in sequence. The mixture was stirred at room temperature under argon for the proper time and then worked up as described above.

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

Reference:
Article; Chelucci, Giorgio; Figus, Susanna; Journal of Molecular Catalysis A: Chemical; vol. 393; (2014); p. 191 – 209;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 115576-91-5, A common heterocyclic compound, 115576-91-5, name is (1-Methyl-1H-benzo[d]imidazol-5-yl)methanol, molecular formula is C9H10N2O, 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 11C : [1-METHYLBENZIMIDAZOLE-5-CARBOXALDEHYDE] A solution of 5-hydroxymethyl-1-methylbenzimidazole (0.8 g, 4 mmol) in acetone (40 [ML)] was treated with [MN02] (4 g) and the mixture was stirred for 3 days. The solid was filtered off and the solvent removed under reduced pressure to give 0.63 g of product. [COHGN2O] Mass (calculated): [160]; (found): [M+H+] = 161. NMR (400 [MHZ, DMSO-D6)] : 3.95 (3H, s, NCH3) ; 7.8 [(1H,] d, J = 8 Hz, aryl-H); 7.9 [(1H,] dd, [J =] 1 and 8 Hz, aryl-H); 8.3 [(1H,] d, J= 1 Hz, aryl-H); 8.45 [(1H,] s, imidazole-H); 10.1 [(1H,] s, CHO).

The synthetic route of 115576-91-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN, INC.; WO2003/99814; (2003); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem