Tag: M.W=100-200

Reference of 496-46-8, A common heterocyclic compound, 496-46-8, name is Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, molecular formula is C4H6N4O2, 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.

3a-isopropylglycoluril dimer diether (compound 2.3) (1 g, 2.5 mmol) and unsubstituted glycoluril (720 mg, 5.0 mmol) were mixed in 7M hydrochloric acid (12 mL). The mixture was stirred at room temperature for 1 hr. The mixture was heated to 100C for 2-3 hr. Evaporation of the acid in vacuo gave the a, P, 5, G-TETRAISOPROPYLCUCURBIT [4,2] uril as the major product.

The synthetic route of 496-46-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNISEARCH LIMITED; WO2005/26168; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 33468-69-8,Some common heterocyclic compound, 33468-69-8, name is 4-(Trifluoromethyl)-1H-imidazole, molecular formula is C4H3F3N2, 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.

Sodium hydride (60% in mineral oil; 0.4 g, 10 mmol) was added portionwise to a stirred solution of 4-(trifluoromethyl)-lH-imidazole (1.15 g, 8.45 mmol) in THF (19 mL) at 0 C. After stirring at 0 C for 30 minutes 2-(trimethylsilyl)ethoxymethyl chloride (1.69 g, 10 mmol) was added and the reaction mixture was stirred at room temperature for 30 minutes. Water was added and the product extracted with EtOAc. The organic layer was separated, dried (MgS04), filtered and the solvent was evaporated in vacuo to yield 4-(trifluoromethyl)-l-{[2-(trimethylsilyl)ethoxy]methyl}- lH-imidazole (2.2 g, 98 % yield) that was used in the next step without further purification.

The synthetic route of 33468-69-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; TRABANCO-SUAREZ, Andres, Avelino; DELGADO-JIMENEZ, Francisca; VEGA RAMIRO, Juan, Antonio; TRESADERN, Gary, John; GIJSEN, Henricus, Jacobus, Maria; OEHLRICH, Daniel; WO2012/85038; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 17325-26-7, 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. 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 25-1 (0.5g, 4.0mmol) in anhydrous THF (15ml) in a dried flask was added NaH (O.lg, 4.8mmol) in portions. Once bubbling had subsided iodopropane (0.8ml, 8.0mmol) was added and stirred at room temperature overnight. To the reaction mixture was added another 0.5eq of NaH was added along with 3eq of iodopropane. After stirring for 5Oh another 0.5eq of NaH was added along with 2eq of iodopropane. The reaction mixture stirred for another 2Oh before being quenched with ethanol (5ml). Solvent removal afforded the desired product 25-2 as a solid. MS calculated M+H: 169.2, found 155.1 (M-CH2).

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

Reference:
Patent; MERCK & CO., INC.; WO2006/135627; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 5805-57-2, name is (1H-Benzo[d]imidazol-2-yl)methanamine, 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 5805-57-2, Safety of (1H-Benzo[d]imidazol-2-yl)methanamine

To a stirred solution of (S)-methyl 2~amino-3~(2,4~ dichiorophenylipropanoate (103 mg, 0.415 mmol) in DCM (10 mL) was added DIPEA ( 1.5 equiv) and cooled to 0 C. A solution of triphosgene (0.33 equiv) in DCM (2 mL) was added dropwise to the reaction mixture and stirred at room temperature for 2 h. The solution was 106 back to 0 C and ( lH-benzo[d]imidazol-2-yl)niethanamine (1.5 equiv) in DCM (2 nil) was added. The reaction mixture was stirred at 0 C for 30niin. The solution washed with brine, dried over anhydrous sodium sulfate and evaporated under vacuum. The residue was purified by flash column chromatography to give (S)-methyi 2-(3-(( lH-benzo[dJimidazol-2- yl)methyl)ureido)-3-(2,4-dich{orophenyl)propanoate.

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, (1H-Benzo[d]imidazol-2-yl)methanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITY OF WASHINGTON; BUCKNER, Frederick, S.; ALVAREZ, Ximena, Barros; FAN, Erkang; GILLESPIE, John, Robert; HOL, Wilhelmus, G.J.; HUANG, Wenlin; KOH, Cho, Yeow; RANADE, Ranae, M.; SHIBATA, Sayaka; VERLINDE, Christophe, L.M.; ZHANG, Zhongsheng; (249 pag.)WO2016/29146; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 104619-51-4, 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. 104619-51-4 name is Di(1H-imidazol-1-yl)methanimine, 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.

An oven dried round bottom flask was charged withdi(IH-imidazol-l-yl)methanimine (500 mg, 3.10 mmol),2-aminophenol (188 mg, 1.724 mmol) and anhydrous THF(20 ml) at room temperature. The resulting suspension wasrefluxed under N2 for 2 hr to give complete conversion basedon LC/MS. The solvent was removed in vacuo and the residuewas purified on a Biotage Flash Collector, eluting with30-80% EtOAc/Hexane (1200 ml) to afford the expectedproduct, benzo[d]oxazol-2-amine (200 mg, 1.5 mmol, 87%yield), as a white solid

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Di(1H-imidazol-1-yl)methanimine, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; COOK II, JAMES H; MCDONALD, IVAR M; KING, DALTON; OLSON, RICHARD E; WANG, NENGHUI; IWUAGWU, CHRISTIANA I; ZUSI, F.CHRISTOPHER; MACOR, JOHN E; (330 pag.)JP5714745; (2015); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature 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.

Sodium hydride (purity 55%)(516 mg, 12.0 mmol) was added to a N,N-dimethylformamide solution (8.0 ml) of 2-chloro-1H-benzimidazole (1.52 g, 10.0 mmol), at 0C, under nitrogen stream, and stirring was carried out for 20 minutes. Methyl iodide (0.750 ml, 12.0 mmol) was further added, and stirring was carried out under room temperature for 2 hours. Water was added to the reaction solution, and the resulting solid substance was collected by filtration to afford 2-chloro-1-methyl-1H-benzimidazole (1.51 g, yield 91%) as a white solid.

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; Daiichi Sankyo Company, Limited; EP2258697; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 2466-76-4, 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. 2466-76-4 name is 1-(1H-Imidazol-1-yl)ethanone, 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.

Step 7: Synthesis of methyl 2-(2-bromophenyl)-3-oxobutanoate: To a stirred solution of methyl 2-(2-bromophenyl)acetate ( 2 g, 8.72 mmol) in dry THF ( 20 mL) at -78 °C, LiHMDS (1M in toluene, 17.4 mL, 17.4 mmol) was added under nitrogen atmosphere and stirring was continued for 1 h. Then a solution of l-(lH-imidazol-l- yl)ethanone (1.15 g, 10.47 mmol) in dry THF:DMF (10 mL: 2mL) mixture was added. The reaction mixture was allowed to warm up to ambient temperature. The progress of the reaction was monitored by TLC. Upon completion the reaction was quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The combined organic layers were dried over sodium sulphate and concentrated under reduced pressure. The crude compound was purified by column chromatography to afford the title compound (2.1 g, 88percent).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(1H-Imidazol-1-yl)ethanone, and friends who are interested can also refer to it.

Reference:
Patent; EPIZYME, INC.; CAMPBELL, John Emmerson; WO2015/10078; (2015); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 53316-51-1, name is 4,5-Dimethyl-1H-imidazole hydrochloride, 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 53316-51-1, category: imidazoles-derivatives

Step 1 : l-(2-((tert-butyldimethylsiIyl)oxy)ethyl)-4,5-dimethyl-lH-imidazole [001009] A solution of 4,5-dimethyl- lH-imidazole hydrochloride (2.94 g, 22.2 mmol) was in N,N-dimethylformamide (30.0 mL, 387 mmol) was cooled to 0 C. Sodium hydride (3.55 g, 88.7 mmol) was slowly added and the solution was stirred for 30 mins at 0 C. Potassium iodide (4.417 g, 26.61 mmol) and (2-bromoethoxy)-tert-butyldimethylsilane (6.365 g, 26.61 mmol) were added and the mixture was allowed to warm to room temperature with stirring over 30 minutes. The reaction as quenched with methanol (3 mL) and diluted with water ( 150 ml). The resulting aqueous mixture was extracted with ethyl acetate (3 x 70 mL). The combined organic portions was washed with brine, dried over Na2S04, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography (0 to 15% MeOH in EtOAc) to provide 4.34g (77%) of the title compound. NMR (400 MHz, Chloroform-Patent; DUFFEY, Matthew O.; ENGLAND, Dylan; FREEZE, Scott; HU, Zhigen; LANGSTON, Steven, P.; MCINTYRE, Charles; MIZUTANI, Hirotake; ONO, Koji; XU, He; (684 pag.)WO2016/4136; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 123470-47-3,Some common heterocyclic compound, 123470-47-3, name is 5,6-Difluoro-1H-benzo[d]imidazole-2(3H)-thione, molecular formula is C7H4F2N2S, 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.

Under argon atmosphere, N-[2,4-bis(2,2,2-trifluoroethoxy)-6-methylpyridin-3-yl]-2-[4-[2-(5,6-difluorobenzimidazol-2-ylthio)ethyl]piperazin-1-yl]acetamide (4.0 g, 8.43 mmol), 5,6-difluoro-2-mercaptobenzimidazole (5.8 g, 31.2 mmol) and triphenylphosphine (7.8 g, 29,7 mmol) were dissolved in N,N-dimethylformamide (170 mL), and under cooling with ice diethyl azodicarbonate (40% w/v toluene solution, 11.0 mL, 25.3 mmol) was added dropwise to the mixture, followed by stirring for 1.5 hours at the same temperature. To the reaction mixture, ethylacetate and 1 mol/L of hydrochloric acid, and aqueous layer was separated. The organic layer was further extracted with 1 mol/L hydrochloric acid. The aqueous layer was combined and the resultant mixture was alkalized by sodium hydroxide (1 mol/L), followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine and then dried over sodium sulfate anhydrate, followed by concentration under reduced pressure. The residue was purified through silica gel column chromatography (developing solvent; chloroform ammonia-saturated methanol=100:3), to thereby yield 2-[4-[2-(5,6-difluorobenzimidazol-2-ylthio)ethyl]piperazin-1-yl]-N-[2,4-bis(2,2,2-trifluoroethoxy)-6-methylpyridin-3-yl]acetamide (4.9 g, yield: 90.1%) as colorless crystals.

The synthetic route of 123470-47-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kowa Co., Ltd.; US2005/20606; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 25676-75-9, A common heterocyclic compound, 25676-75-9, name is 4-Bromo-1-methylimidazole, molecular formula is C4H5BrN2, 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.

Intrmdiate Example 11.5-(I-Methyl-1H-imidazol-4-yl)-1H-benzo[d]imidazolea) 4-(1-Methyl-1H-imidazol-4-yl)-2-nitroanilineA solution, of 2-nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline(1.45 g, 5.55 mmol, 1.1 eq) in 1 ,2-dimethoxyethane (15 ml) was degassed by N2bubbling for 5 mi 4-Bromo-1-methyi-1H-imidazole (0.81 g, 5 mmol, 1 eq) was added and the mixture was degassed for another 5 mm. Pd(dppf)Cl2 (0.4 g, 0.5 mmol, 0.1 eq) and aqueous sodiumcarbonate (1.59 g, 15 mmol, 3 eq) were added, sequentially using the procedure of Intermediate Example 1 and then heated at 100 C for 4 h. The reactionmixture was then quenched and extracted as in Intermediate Example 1. The solvent was distilled off to afford the crude residue which was purified by columnchromatography (60-120 silica gel, 50 % ethyl acetate in hexane) to afford the title product in 60 % yield (0.6 g). LC-MS (ESI): Calculated mass: 218.08; Observed mass:219.2 [M+HJ (rt: 0.09 mm).

The synthetic route of 25676-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ORION CORPORATION; RAJAGOPALAN, Srinivasan; APPUKUTTAN, Prasad; NARASINGAPURAM ARUMUGAM, Karthikeyan; UJJINAMATADA, Ravi Kotrabasaiah; GEORGE, Shyla; LINNANEN, Tero; WO2014/162039; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem