Month: September 2021

Some common heterocyclic compound, 3034-50-2, name is Imidazole-4-carbaldehyde, 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. Application In Synthesis of Imidazole-4-carbaldehyde

12.0 g (124 mmol) 4-formyl-imidazole are placed together with 750 mg Raney nickel in 1000 ml of methanolic ammonia solution and shaken at 40 C. for 30 min. Then the mixture is hydrogenated in a Parr apparatus under a hydrogen atmosphere at 5 bars pressure at 40 C. for 14 h. Another 750 mg Raney nickel are then added and the mixture is again hydrogenated at 50 C. under a hydrogen atmosphere at 5 bars pressure for 14 h. The mixture is filtered, evaporated down i. vac., and in each case methanol, toluene and ethanol are added to the residue and it is again evaporated down completely i. vac. The residue is combined with ethereal hydrochloric acid in methanol and evaporated down completely i. vac. The residue is in each case combined with methanol and dichloromethane and evaporated down completely i. vac.Yield: 21.2 g (quant.)Rt value: 0.49 min (D)C4H7N3*2 HCl (170.04/97.12)Mass spectrum: (M+H)+=98

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3034-50-2, its application will become more common.

Reference:
Patent; Dahmann, Georg; Gerlach, Kai; Pfau, Roland; Priepke, Henning; Wienen, Wolfgang; Schuler-Metz, Annette; Nar, Herbert; US2008/51578; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 2034-22-2, name is 2,4,5-Tribromoimidazole, molecular formula is C3HBr3N2, 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: C3HBr3N2

PRODUCTION EXAMPLE 3 [PRODUCTION OF THE PRESENT COMPOUND (3)] To a solution of a sodium salt, prepared from 1.22 g of 2,4,5-tribromoimidazole and 0.16 g of 60% oil-based sodium hydride, in 5 ml of N,N-dimethylformamide was added dropwise 1.23 g of 4-bromobutoxymethyl bromide at room temperature. After stirring at room temperature for 3 hours, 50 ml of water was added to the reaction mixture which was then extracted with three 30-ml portions of ether. The ether layer was dried over magnesium sulfate and concentrated. The oily product obtained was purified by column chromatography on silica gel to obtain 0.74 g of 1-(4-bromobutoxymethyl)-2,4,5-tribromoimidazole.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2034-22-2, its application will become more common.

Reference:
Patent; Sumitomo Chemical Company, Limited; US4689340; (1987); 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 18075-64-4 as follows. Recommanded Product: 18075-64-4

Example 151 1-Phenyl-1H-imidazole-4-carboxylic acid {2-oxo-2-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethyl}-amide DIPEA (186 mg, 1.4 mmol) was added to a stirred solution of 1-phenyl-1H-imidazole-4-carboxylic acid (60 mg, 0.32 mmol) in DMF (5 mL) followed by HOBt (47 mg, 0.35 mmol) and EDCI (153 mg, 0.8 mmol). After 2 minutes of stirring, 2-amino-1-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethanone hydrochloride (119 mg, 0.35 mmol) (prepared according to Step 1 and 5 of the General Scheme) was added and the resulting mixture was stirred at ambient temperature overnight. The reaction mixture was diluted with cold water, the solid was collected to afford the 129 mg (86% Yield) of 1-phenyl-1H-imidazole-4-carboxylic acid {2-oxo-2-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethyl}-amide. LC/MS [M+H]+: Purity: 473 (M+1), 96.61%. 1H NMR (300 MHz, DMSO-d6): delta 8.4 (s, 1H), 8.32 (s, 1H), 8.08 (t, 1H), 7.8 (d, 2H), 7.6-7.48 (t, 3H), 7.46 (t, 1H), 7.36-7.24 (t, 3H), 4.9 (s, 1H), 4.2 (d, 2H), 4.0 (bs, 1H), 3.8 (bs, 1H), 3.5 (d, 2H), 2.1 (t, 2H), 1.8 (d, 2H).

According to the analysis of related databases, 18075-64-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Forest Laboratories Holdings Limited; US2009/239810; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 51605-32-4, These common heterocyclic compound, 51605-32-4, name is Ethyl 5-methyl-1H-imidazole-4-carboxylate, 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. To a stirred suspension of ethyl 4-methyl-1H-imidazole-5-carboxylate (2.00 g, 13.0 mmol) in acetonitrile (25 mL) and chloroform (25 mL) was added N-bromosuccinimide (2.31 g, 13.0 mmol). The reaction mixture was stirred under nitrogen atmosphere for 20 h, then concentrated in vacuo. The residue was dissolved in ethyl acetate (100 mL) and washed with saturated aqueous sodium bicarbonate (50 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluding with 50percent ethyl acetate in hexanes to afford ethyl 2-bromo-4-methyl-1H-imidazole-5-carboxylate as a light yellow solid (1.88 g, 62percent): 1H NMR (300 MHz, CDCl3) delta 4.35 (q, J=7.1 Hz, 2H), 2.51 (s, 3H), 1.37 (t, J=7.1 Hz, 3H); MS (ES+) m/z 233.1 (M+1), 235.1 (M+1).

The synthetic route of 51605-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dales, Natalie; Fonarev, Julia; Fu, Jianmin; Hou, Duanjie; Kamboj, Rajender; Kodumuru, Vishnumurthy; Pokrovskaia, Natalia; Raina, Vandna; Sun, Shaoyi; Zhang, Zaihui; US2009/156615; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 4857-06-1, 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. 4857-06-1 name is 2-Chloro-1H-benzo[d]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.

General procedure: 2-Chloro-1H-benzoimidazole (3.04 g, 20 mmol) was dissolved in dry DMF (15 mL) at 0 C, to the solution was added NaH (0.91 g, 22.7 mmol), and the mixture was stirred for 1 h at 0 C, then halide (21.6 mmol) was added. The mixture was stirred overnight at room temperature and was poured into water (50 mL) and stirred for 1 h, filtrated, washed with water and dried to afford 4a-d.

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

Reference:
Article; Luo, Yu; Xiao, Feng; Qian, Shijing; Lu, Wei; Yang, Bo; European Journal of Medicinal Chemistry; vol. 46; 1; (2011); p. 417 – 422;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 288-32-4, name is 1H-Imidazole, molecular formula is C3H4N2, 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. Product Details of 288-32-4

(1) the addition of water in the reactor 10 kg, the previous batch filtrate 8 kg (filtrate all recovery use, so there is no discharge), imidazole 2.6 kg, potassium hydroxide 3.9 kg, batchwise by adding bromine 4.8 kg, canada finishes, controlled to disappear in the raw materials, the reaction temperature is controlled in the 80 – 90 C). Adding concentrated hydrochloric acid to adjust the pH to 7 the left and right, a large quantity of solid precipitate (mostly 4 – bromo – 1H – imidazole and a little double bromine substituted imidazole). Filtering after-filtration cake (4.3 kg, yield 90%) can be directly into the next step of the reaction, the filtrate as the solvent directly used in the next batch (non-sewage disposal).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 288-32-4, its application will become more common.

Reference:
Patent; Hangzhou Lide Biological Technology Co., Ltd.; Ren Guobao; Wu Yan; Li Chuanbin; (5 pag.)CN106674121; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 4857-06-1, 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. 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows.

2-chloro- 1 -methyl- 1 H-benzo [d] imidazole[670] To a solution of 2-chloro- lH-benzo[d]imidazole (2.0 g, 13.1 mmol) in DMF(10 mL) was added NaH (0.63 g, 15.7 mmol) at 0 C under N2. After stirring for 30 min at 0 C, iodomethane (5.58 g, 39.3 mmol) was added and the mixture was stirred at room temperature for additional 1 hour. The reaction mixture was quenched with water (100 mL). The aqueous layer was extracted with EtOAc (3 x 20 mL). The combined organic layers were dried over a2S04, filtered, and concentrated to give the title compound (1.9 mg, 8.9 mmol, 67.9 % yield) as a white solid. MS: MS (M+H)+; XH NMR (400 MHz, CDC13): ? 7.71-7.68 (m, 1H), 7.31-7.27 (m, 3H), 3.79 (s, 3H).

The chemical industry reduces the impact on the environment during synthesis 2-Chloro-1H-benzo[d]imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ABBVIE INC.; BAYBURT, Erol K.; CLAPHAM, Bruce; COX, Phil B.; DAANEN, Jerome F.; GOMTSYAN, Arthur; KORT, Michael E.; KYM, Philip R.; VOIGHT, Eric A.; SCHMIDT, Robert G.; DART, Michael J.; GFESSER, Gregory; WO2013/62966; (2013); 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. 32673-41-9, name is 4-Imidazolemethanol hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., Safety of 4-Imidazolemethanol hydrochloride

Step A Preparation of 1-triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of 4-(hydroxymethyl)imidazole hydrochloride (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenyl-methane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid.

According to the analysis of related databases, 32673-41-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dinsmore, Christopher J.; Bergman, Jeffrey M.; US2002/52380; (2002); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 15965-54-5, 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. 15965-54-5 name is 2-Chloro-5-methoxy-1H-benzo[d]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.

To 2-chloro-5-methoxy-1H-benzo[djimidazole (13.04 mg, 0.071 mmol) and Intermediate I-i (20 mg, 0.059 mmol) was added toluene (0.75 mL) and EtOH (0.25 mL). The reaction mixture was stirred at room temperature until solids are dissolved, then [1,1 ?-Bis(diphenylphosphino)ferrocenej dichloropalladium (II) complex with dichloromethane (1:1) (5.83 mg, 7.14 imol) was added. The flask was degassed andflushed with argon. Finally sodium carbonate (0.059 mL, 2M, 0.119 mmol) was added dropwise. The reaction vessel was sealed and bubbled with argon for 5 mm, then placed in microwave reactor at 140 C for 30 mm. The reaction mixture was cooled to room temperature and was diluted with EtOAc and water, extracted with EtOAc (3X). The combined organic layer was washed with brine, dried with Mg504 and concentrated. Thecrude sample was purified with a preparative HPLC (method A, 30-100% B in 8 mm.). The desired fractions were placed in a SpeedVac overnight to remove solvent, then lyophilized to give Example 50 (6 mg, 0.016 mmol, 27.5 % yield). ?H NMR (acetonitrile-d3, 400MHz): = 8.77 (br. s., 2H), 7.70 (s, 3H), 7.27-7.39 (m, 1H), 7.05-7.18 (m, 1H), 3.90 (s, 3H), 2.65 ppm (s, 3H). ?9F NMR (acetonitrile-d3, 376MHz):= -76.64 (br. s., 3F), -90.69 ppm (s, 2F). LC-MS: method C, RT = 1.78 mm, MS (ESI) m/z: 357.0 (M+H). Analytical HPLC purity (method A): 98%

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-5-methoxy-1H-benzo[d]imidazole, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ZHANG, Xiaojun; PRIESTLEY, Eldon Scott; BATES, J. Alex; HALPERN, Oz Scott; REZNIK, Samuel Kaye; RICHTER, Jeremy M.; (1137 pag.)WO2018/13774; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem