Month: December 2020

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. 1849-01-0

Preparation of l-(3-iodopropyl)-3-methyl-l -benzor< |imidazol-2(3H)-one; [0176] A mixture of l-methyl-lH-benzo[i ]imidazol-2(3H)-one (2 g, 13.5 mmol, 1 equiv), 1- bromo-3-chloropropane (3.98 ml, 40.5 mmol, 3 equiv), and potassium carbonate (2.79 g, 20.25 mmol, 1.5 equiv) in NN-dimethylformamide was heated at 65C for 16 h. The reaction was cooled to ambient temperature and diluted with ethyl acetate. After being washed with water and brine, the organic layer was dried over MgS04, filtered, and concentrated in vacuo. The resulting residue was purified using the Biotage chromatography system (SNAP lOOg cartridge, Rf = 0.6, gradient - 10%- 50%) ethyl acetate/hexanes) to afford l-(3-chloropropyl)-3-methyl-lH-benzo[i ]imidazol-2(3H)-one as a clear oil (2.57 g, 85%); 'ffNMR (400 MHz, DMSO-i/6): delta 2.05-2.12 (m, 1H); 2.14-2.21 (m, 1H); 3.32 (s, 3H); 3.53 (t, 1H, J= 6.8 and 6.4 Hz); 3.66 (t, 1H, J= 6.4 Hz); 3.92-3.97 (m, 2H); 7.05- 7.09 (m, 2H); 7.12-7.16 (m, 1H); 7.17-7.21 (m, 1H); MS for CiiH13ClN20 m/z 226.07 (M+H)+. Statistics shows that 1849-01-0 is playing an increasingly important role. we look forward to future research findings about 1-Methyl-1H-benzo[d]imidazol-2(3H)-one. Reference:
Patent; ALTOS THERAPEUTICS, LLC; LUEHR, Gary, W.; SUNDARAM, Arathi; JAISHANKAR, Priyadarshini; PAYNE, Philip, W.; DRUZGALA, Pascal; WO2011/160084; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding some certain compound to certain chemical reactions, such as: 1792-40-1, name is 2-Methyl-5-nitro-1H-benzo[d]imidazole, 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 1792-40-1. 1792-40-1

To a solution of 2-methyl-5-nitro-1H-benzimidazole (2) (9.0 g,0.05 mol) in ethanol (50 mL), K2CO3 (6.98 g, 0.075 mol) and benzylchloride (9.63 g, 0.075 mol) were refluxed for 8 h. After the completionof the reaction (monitored by TLC), the reaction mixturewas filtered and concentrated to give yellow solid. The residualmass was crystallized from ethanol to give mixture of 1-benzyl-2-methyl-5-nitro-1H-benzimidazole and 3-benzyl-2-methyl-5-nitro-3H-benzimidazole (3) in 75% yield. To a suspension of SnCl2 2H2O (15.45 g, 0.067 mol) in 2 N HCl (47.6 mL), 1/3-benzyl-2-methyl-5-nitro-1H/3H-benzimidazole (3) (4.25 g, 0.019 mol)was heated at 110 C for 7 h. After completion of the reaction,the suspension was neutralized with 2 N NaOH and diluted withethanol. Filtered the solid product and extracted the filtrate with chloroform, dried over Na2SO4, filtered and concentrated to getmixture of products which were separated through column chromatographyusing ethyl acetate/methanol (19:1) as eluent to getsolid compounds 4a and 4b.

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 2-Methyl-5-nitro-1H-benzo[d]imidazole.

Reference:
Article; Singla, Prinka; Luxami, Vijay; Paul, Kamaldeep; Bioorganic and Medicinal Chemistry; vol. 23; 8; (2015); p. 1691 – 1700;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A common compound: 705-09-9, name is 2-(Difluoromethyl)-1H-benzo[d]imidazole, belongs to imidazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 705-09-9

A mixture of 2-difluoromethyl-lH-benzimidazole (7.57 g), 2,4-dichloro-6-morpholinopyrimidine (11.7 g), sodium bicarbonate (21 g) and DMF (100 ml) was stirred under nitrogen and heated to 110C for 20 hours. The resultant mixture was cooled, filtered and the filtrate was evaporated. The resultant product was purified by column chromatography on silica using increasingly polar mixtures of ethyl acetate and methylene chloride as eluent. The solid so obtained was a mixture of major and minor isomeric products. The solid was washed with a mixture of isohexane (400 ml) and diethyl ether (400 ml). The washings were evaporated to give a Residue [A]. The washed solid was recrystallised from warm methylene chloride (30 ml) by the addition of isohexane (120 ml). The resultant crystalline solid was isolated and washed with a mixture of diethyl ether (300 ml) and isohexane (300 ml) and the washings were again evaporated to give a Residue [B]. Residues [A] and [B] were combined and purified using a Waters ‘Xterra’ preparative reversed-phase column (5 microns silica, 19 mm diameter, 100 mm length) using decreasingly polar mixtures of water [containing 1% aqueous ammonium hydroxide (d = 0.88)] and acetonitrile as eluent. There was thus obtained a sample of the minor isomeric product, namely 2-chloro- 4-(2-difluoromethylbenzimidazol-l-yl)-6-morpholinopyrimidine (0.173 g); NMR Spectrum: (DMSOd6) 3.73 (s, 8H), 7.2 (s, IH), 7.44-7.52 (m, 2H), 7.51 (t, IH), 7.77-7.79 (m. IH), 7.88-7.90 (m, IH); Mass Spectrum: M+H+ 366.

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, 705-09-9, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BUTTERWORTH, Sam; GRIFFEN, Edward, Jolyon; PASS, Martin; WO2008/32060; (2008); A1;,
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. 3034-50-2, name is Imidazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., 3034-50-2

(i) Preparation of 1-(triphenylmethyl)-1H-imidazol-4-carboxaldehyde (7): To a stirred suspension of 4-imidazole carboxaldehyde (from Maybridge Chemicals, United Kingdom) (35.0 g, 364 mmol) and triethylamine (55.8 mL; 400 mmol) in dichloromethane (2 L), was added a solution of triphenylmethyl chloride in dichloromethane (600 mL) while maintaining the reaction temperature at approximately 15 C. with a cooling bath. The resultant solution was warmed to room temperature and stirred for 19 h. Washed the reaction solution with a solution of saturated brine and water (1:3.5; 3*600 mL), followed by brine (1*800 mL). Dried over sodium sulfate; filtered to remove drying agent; and removed solvent under vacuum to obtain the desired tritylated product (7) as an off-white solid. MP 186.5-194 C. [Trituration of this product with ether yielded a cream-colored powder with mp 195-197 C.]

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:
Patent; Shih, Neng-Yang; Aslanian, Robert G.; Piwinski, John J.; Lupo JR., Andrew T.; Afonso, Adriano; US2002/82272; (2002); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

3273-68-5, 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 3273-68-5 as follows.

Preparation 4; 5,6-Dihydroimidazor4.5.1-/7c1f1lbenzazepine-2,7(1H,4H)-dione; To a solution of the compound of Preparation 5 (45.0 g, 0.2 mol) in dichloromethane (150 ml) was added thionyl chloride (30 ml, 0.4 mol) and the reaction mixture was stirred at room temperature for 2 h. The mixture was concentrated in vacuo and to the residue was added dichloromethane (1000 ml) and aluminium chloride (84.0 g, 0.6 mol), added portionwise. After stirring at room temperature overnight, the reaction mixture was heated under reflux for 2 h and then concentrated in vacuo. To the residue was added ice water (2000 ml) and concentrated hydrochloric acid (50 ml), followed by additional ice water(2000 ml). The resulting precipitate was collected by filtration, washed with water (4 x 250 ml) and dissolved in sodium hydroxide solution (1 N, 600 ml). The solution was washed with dichloromethane (2 x 150 ml) and cyclohexane (150 ml) and adjusted to pH 10 by addition of dry ice. The solid material was collected by filtration, washed with water (3 x 50 ml) and dried overnight at 40C to give the title compound (30.0 g).1H-NMR (cfe-DMSO): 2.03 – 2.11 (2H), 2.90 – 3.00 (2H), 3.85 – 3.95 (2H), 7.02 – 7.10 (1 H), 7.17 – 7.24 (1 H), 7.50 – 7.58 (1 H)

According to the analysis of related databases, 4-(2-Oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)butanoic acid, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER LIMITED; WO2008/44127; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 145022-45-3, name is 1-Ethyl-3-methylimidazolium Methanesulfonate, molecular formula is C7H14N2O3S, 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. 145022-45-3

For the Emim3[PMo12O40] (from this point forward Emim-Mo)synthesis [30], appropriate quantities of prepared H3PMo12O40(0.9 g) and 1-ethyl-3-methylimidazolium methanesulfonate (Alfa Aesar) were dissolved in distilled water (20 mL) separately. When mixed, a precipitate was formed, then filtered and dried at room temperature. Another two hybrids were analogously prepared by using 1-butyl-3-methylimidazolium methanesulfonate (Sigma Aldrich) to produce the Bmim3[PMo12O40] (Bmim-Mo) and 1-hexyl-3-methylimidazolium chloride (Alfa Aesar) for Hexmim3[PMo12O40] (Hexmim-Mo). All the hybrids were used asprepared and their structures are presented in Fig. 1

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 145022-45-3, its application will become more common.

Reference:
Article; Megias-Sayago; Carrasco; Ivanova; Montilla; Galindo; Odriozola; Catalysis Today; vol. 278; (2016); p. 82 – 90;,
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 71759-89-2 as follows. 71759-89-2

N,N’-Dimethylsulfonamide chloride (550 muL, 5.16 mmol) was added to a stirring solution of 4-iodoimidazole (500 mg, 2.58 mmol) and TEA (0.90 mL, 6.44 mmol) in ACN (5 mL) at room temperature. After 2 hours, the mixture was concentrated on silica and subjected to flash column chromatography (10-40% EtOAc/hexane gradient) to afford 4-iodo-imidazole-1-sulfonic acid dimethylamide as white solid (620 mg, 80%). 1H NMR (CDCl3, 300 MHz) delta 1.34 (s, 6H), 5.78 (s, 1H), 6.23 (s, 1H); MS (ESI) m/z=301.9 (MH+).

According to the analysis of related databases, 71759-89-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Genelabs Technologies, Inc.; US2010/204265; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

3034-42-2, Adding a certain compound to certain chemical reactions, such as: 3034-42-2, name is 1-Methyl-5-nitroimidazole, 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 3034-42-2.

In a sealed glass tube, formaldehyde (1 g, 33.54 mmol) and 1-Methyl-5-nitro-1H-imidazole (4a) (1 g, 7.8 mmol) solution were added in DMSO (5 mL). The tube was heated at 140 C for 48 h. After that solution was poured into water (5 mL) and extracted with ethyl acetate (3 x 5 mL). Then mixture was dried (MgSO4) and solvent evaporation under vacuum, gave crude in the form of solid, which was recrystallized (THF/heptane, 1:1) and product (5a) was isolated (0.76 g, 62% yield) as white powder; m.p. 117 C.

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-Methyl-5-nitroimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Samant, Bhupesh S.; Sukhthankar, Mugdha G.; Bioorganic and Medicinal Chemistry Letters; vol. 21; 3; (2011); p. 1015 – 1018;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

2849-93-6, 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 2849-93-6 as follows.

Diisopropylethylamine (2.2 [MMOL)] was added to a solution of benzimidazole-2- carboxylic acid (3.59 [MMOL),] [0- (7-AZABENZOTRIAZOL-1-YL)-N, N, N’, N’-] [TETRAMETHYLURONIUM] hexafluorophosphate (HATU, 3.00 [MMOL),] 1-hydroxy-7- [AZABENZOTRIAZOLE] (HOAT, 3.00 [MMOL),] and 1-methylpiperazine (2.00 [MMOL)] in DMF (0.5 M). The reaction mixture was allowed to stir at room temperature overnight. The solvent was removed, and the residue was dissolved in EtOAc. The solution was washed with 1 N HCI, satd aq [NAHCO3] and brine. It was then dried [(NA2SO4),] filtered, and concentrated to obtain the crude product as a viscous oil, which was purified on silica gel (40 g; 3-10% methanol (2 M NH3)/dichloromethane), yielding the title compound (1.68 mmol, 47%). Elemental analysis: calculated for [C13H16N4O,] C 63.91, H 6.60, N 22.93 ; found C 63.76, H 6.79, N 22.87. The MS [AND 1H] NMR data matched that of the sample prepared above.

According to the analysis of related databases, 1H-Benzimidazole-2-carboxylic acid, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2004/22060; (2004); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

41716-18-1, 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. 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of intermediate 42-h.HCl (1.50 g, 2.24 mmol) in DMF, cooled to 0¡ã C., were sequentially added 1-methyl-1H-imidazole-4-carboxylic acid (397 mg, 3.15 mmol), HATU (1.19 g, 3.15 mmol) and DIPEA (1.57 mL, 8.99 mmol) and the reaction mixture was stirred at room temperature for 2 hours. Saturated aqueous ammonium chloride and ethyl acetate were added; the organic layer was separated, washed with saturated aqueous ammonium chloride, saturated aqueous NaHCO3 and brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification by silica gel chromatography provided intermediate 43-a as a white foam.

The synthetic route of 41716-18-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pharmascience Inc.; Laurent, Alain; Proulx, Melanie; Rose, Yannick; Denissova, Irina; Dairi, Kenza; Jarvis, Scott; Jaquith, James B.; (189 pag.)US9284350; (2016); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem