Tag: M.W=300-400

Electric Literature of 1219741-21-5, 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. 1219741-21-5, name is 5-Chloro-6-iodo-1H-benzo[d]imidazole-2(3H)-thione belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

K2CO3 (0.22 g, 1.61 mmol), followed by iodomethane (0.1 mL, 1.61 mmol), was added to a solution of 5-chloro-6-iodo- 1 ,3- dihydro-2H-benzimidazole-2-thione (I g, 3.22 mmol) in acetone (20 mL) at O0C. The reaction was stirred at rt for 1 h. Additional K2CO3 (1.61 mmol) and iodomethane (1.61 mmol) were added, and stirring continued at rt overnight. Volatiles were removed and the residue was partitioned between EtOAc and water. Concentration afforded the desired product as a white foam, which was used in the next step without further purification.

The synthetic route of 5-Chloro-6-iodo-1H-benzo[d]imidazole-2(3H)-thione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; METABASIS THERAPEUTICS, INC.; BOOKSER, Brett, C.; DANG, Qun; GIBSON, Tony, S.; JIANG, Hongjian; CHUNG, De Michael; BAO, Jianming; JIANG, Jinlong; KASSICK, Andy; KEKEC, Ahmet; LAN, Ping; LU, Huagang; MAKARA, Gergely, M.; ROMERO, F., Anthony; SEBHAT, Iyassu; WILSON, David; WODKA, Dariusz; WO2010/47982; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 15469-97-3, 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. 15469-97-3 name is 1-Trityl-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 55 STR85 Preparation of (+-)trans-4-(2-(4-cyclohexylbut-1-ynyl)cyclopropyl)imidazole (55). (+-)trans-4-(2-(4-Cyclohexylbut-1-ynyl)cyclopropyl)imidazole was prepared as described for the Example 38 except recemic mixture of 4-(2-ethylnylcyclopropyl)-1-(triphenylmethyl)imidazole and 2-cyclopentyl iodoethane were used. (+-)trans-4-(2-(4-cyclohexylbut-1-ynyl)cyclopropyl)imidazole (55). 1 H-NMR (300 MHz, CD3 OD): delta 7.51 (s, 1H), 6.81 (s, 1H), 2.14 (m, 2H), 2.04 (m, 1H), 1.72 (m, 5H), 1.42 (m, 1H), 1.35 (m, 3H), 1.29-1.02 (m, 5H), 0.9 (m, 2H); MS (Cl) m/e 243(M+1).

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

Reference:
Patent; Gliatech, Inc.; US6008240; (1999); A;,
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. 33016-47-6, name is 1-Trityl-1H-imidazole-4-carbaldehyde, A new synthetic method of this compound is introduced below., Quality Control of 1-Trityl-1H-imidazole-4-carbaldehyde

Step 8.c. 7-((1-Triphenylmethyl-imidazol-4-yl)methyl)-2-(2-methoxyphenyl)-8-(1-methylpropyl)- 5,6,7,8-tetrahydro-imidazo[1,2-a]pyrazine 8-(1-Methylpropyl)-2-(2-methoxyphenyl)-5,6,7,8-tetrahydro-imidazo[1,2-a]pyrazine dihydrochloride (compound vii where R3 is 1-methylpropyl, R4 is 2-methoxyphenyl, and R5-R7 are H) (from Step 4.g.)(179 mg, 0.50 mmol) and the product from Step 8.b. (compound xiv where R2 is H) (338 mg, 1.00 mmol) were combined in 1,2-dichloroethane (2.0 ml). NaBH(OAc)3 (212 mg, 1.00 mmol) was added and the reaction was allowed to stir at room temperature for about 1 hour.. The reaction mixture was poured onto a silica gel column and the product was eluted using EtOAc as eluant.. Product fractions were combined and concentrated to yield pure product as white foam (150 mg, 49%).. Mass spec. 608.2, MH+.

The synthetic route of 33016-47-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SOCIETE DE CONSEILS DE RECHERCHES ET D’APPLICATIONS SCIENTIFIQUES (S.C.R.A.S.); EP1382607; (2004); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 33016-47-6,Some common heterocyclic compound, 33016-47-6, name is 1-Trityl-1H-imidazole-4-carbaldehyde, molecular formula is C23H18N2O, 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 mixture comprising compound 158B (350 mg; 0.88 mmol) and 1-trityl-1H-imidazole-4-carboxaldehyde (352 mg; 1.00 mmol) dissolved in 1,2-dichloroethane (DCE) (4.5 ml) in the presence of acetic acid (0.3 ml) is stirred for 5 minutes at room temperature and sodium triacetoxyborohydride (233 mg; 1.10 mmol) is then added. The mixture is stirred overnight at room temperature and is then diluted with ethyl acetate and washed successively with saturated NaHCO3 solution, with water, and with saturated aqueous sodium chloride solution. The organic phase is dried over magnesium sulfate, filtered and concentrated. This crude reaction, product is then purified by flash chromatography (gradient: 4/1 and then 2/1 CH2Cl2/acetone) to give the desired product (304 mg; 48%). [0268] 1H NMR, DMSO-d6 (ppm): 1.88 (m, 2H); 2.00 (s, 3H); 2.33 (m, 2H); 3.63 (s, 3H); 4.03 (d, 2H, 5.2 Hz); 4.50 (m, 1H); 5.45 (t, 1H, 5.6 Hz); 6.55 (s, 1H); 6.70 (s, 1H); 6.76 (d, 1H, 8.7 Hz); 7.01 (m, 6H); 7.21 (d, 1H, 8.7 Hz); 7.25 (s, 1H); 7.31-7.41 (m, 13H); 7.55 (d, 1H, 7.4 Hz); 7.73 (d, 3H, 9.4 Hz); 11.35 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Trityl-1H-imidazole-4-carbaldehyde, its application will become more common.

Reference:
Patent; Perez, Michel; Lamothe, Marie; Hill, Bridget; Etievant, Chantal; US2004/204417; (2004); 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. 87941-55-7, name is 4-Bromo-1-trityl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C22H17BrN2

Example 226: N-[3-(1H-imidazol-4-yl)phenyl]-1-oxo-2,3,4,5-tetrahyd][1,4]diazepino[1,2-a]indole-8-carboxamide Step 1: Synthesis of 3-(l-trityl-1H-imidazol-4-yl)aniline (3-Aminophenyl)boronic acid (1.0 g, 7.3 mmol), 4-bromo-1-trityl-1H-imidazole (2.8 g, 7.3 mmol), tri-i-butylphosphonium tetrafluoroborate (424 mg, 1.5 mmol) and KF (1.4 g, 24.1 mmol) are added into dry THF (20 mL) and argon is bubbled through the mixture for 10 min. Tris-(dibenzylideneacetone) dipalladium(O) (669 mg, 0.7 mmol) is added and the reaction mixture is sealed and heated at 60 C for 16 h. The solid is filtered and the filtrate is diluted with EtOAc (250 mL). The solution is washed with water (3×100 mL), brine (100 mL), dried (Na2S04) and concentrated. The crude material is purified by flash column chromatography using methanol in CH2C12 to afford the title compound (1.1 g, 36%).

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 87941-55-7.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOYER, Stephen, James; GAO, Donghong, Amy; GUO, Xin; KIRRANE, Thomas, Martin, Jr.; SARKO, Christopher, Ronald; SNOW, Roger, John; SOLEYMANZADEH, Fariba; ZHANG, Yunlong; WO2011/71716; (2011); A1;,
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 2034-22-2 as follows. Safety of 2,4,5-Tribromoimidazole

Step 1: N-(2.4.5-tribromo-l-(r2-(trimethylsilv?ethoxy1methyl|-lH-imidazole (A1); To a solution of 2,4,5-tribromo-imidazole in THF was added portionwise sodium hydride (1 eq.). The mixture was stirred for 20 min at RT and SEM-Cl (1 eq.) was added. The mixture was left stirring for 16 h at RT. After dilution with Et2O the suspension was filtered and the clear solution was concentrated to dryness under reduced pressure. The oily residue was dissolved in PE/ 5% EtOAc and applied on a silicagel column. After washing with PE/ 5% EtOAc the product was eluted with PE/ 10% EtOAc. The solvents were removed under vacuum to afford the title compound as a white solid. 1U NMR (400 MHz, CDCl3) delta: 5.31 (s, 2H), 3.59 (t, J=7.8 Hz, 2H), 0.92 (t, J=7.8 Hz, 2H), 0.01 (s, 9H).

According to the analysis of related databases, 2034-22-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI SPA; WO2008/56187; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 17464-88-9, A common heterocyclic compound, 17464-88-9, name is 1,3,4,6-Tetrakis(methoxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, molecular formula is C12H22N4O6, 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.

The Amberlyst 15 resin was dried in an oven to 60% of the original weight.3 g of tetramethoxymethylglycoluril was added to a 250 ml three-necked flask, 6 g of Amberlyst15 resin after drying, and 70 g of PGME were added, and the temperature was raised to 60 C. The reaction was stirred at -0.07 MPa for 17 hours while the produced methanol was distilled off.The reaction was filtered through a Buchner funnel and the filter was washed twice with PGME to recover the resin.The filtrate and the washing solution were combined and the solvent PGME was distilled off under reduced pressure to obtain 5.19 g of 1,3,4,6-tetrakis (1′-methyl-2′-methoxy) ethoxymethylglycol, 99.8%

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:
Patent; Shanxi Medical University; Zhao Zhengbao; Liang Rui; Zhang Jiancheng; Liu Ruiling; Wei Xiao; Li Feifei; (7 pag.)CN105085532; (2017); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 33016-47-6, 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. 33016-47-6 name is 1-Trityl-1H-imidazole-4-carbaldehyde, 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.

(a) 1-triphenylmethyl-4-[(1-hydroxy-1-phenyl)methyl]-1H-imidazole Prepared by reacting 4-formyl-1-triphenylmethyl-1H-imidazole (melting point: 202-205 C.; prepared by oxidation of the corresponding 4-hydroxymethyl compound with manganese dioxide in dioxane) with phenylmagnesium bromide in dry THF. Yield: 94% of theory; Melting point: 187-191 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Trityl-1H-imidazole-4-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; Boehringer Ingelheim Pharma KG; US6043254; (2000); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 2034-22-2, 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 2034-22-2 as follows.

Preparation 15-Bromo-2-ethoxy-3H-imidazole-4-carbaldehyde 2,4,5-Tribromo-1H-imidazole (1a) (98.7 g, 324 mmol, 1.0 eq) was dissolved into 1.20 L of DCM and cooled to 0 C. To this was added DIPEA (62 mL, 360 mmol, 1.1 eq) followed by the slow addition of [beta-(trimethylsilyl)ethoxy]methyl chloride (60.2 mL, 340 mmol, 1.05 eq). The solution was slowly warmed to room temperature. After 2 hours the mixture was washed with 1M H3PO4/saturated aqueous NaCl (1:10; 2×600 mL). The organic layer was dried over MgSO4, and evaporated to dryness, yielding intermediate (1b) as faint yellow liquid that solidified on standing (137 g).Intermediate (1b) (130 g, 290 mmol, 1.0 eq) was dissolved into anhydrous EtOH (650 mL). To this was slowly added potassium t-butoxide (98.6 g, 879 mmol, 3.0 eq) and the mixture was heated to reflux for 16 hours. The mixture was then cooled to room temperature, filtered and concentrated. The resulting oil was dissolved in EtOAc (800 mL) and washed with saturated NaHCO3 (400 mL). The layers were separated and the organic was washed with saturated aqueous NaCl, dried over MgSO4, filtered and concentrated, yielding intermediate (1c) as a brown oil (115.3 g). MS m/z: [M+H+] calcd for C11H20Br2N2O2Si, 401.9 found 401.2.Intermediate (1c) (69.5 g, 174 mmol, 1.0 eq) was dissolved in anhydrous THF (600 mL) and cooled to -78 C. under nitrogen. A 2.5M solution of n-butyllithium in hexanes (72.9 mL, 180 mmol, 1.05 eq) was added dropwise and the mixture was stirred at -78 C. for 10 minutes. DMF (40 mL, 520 mmol, 3.0 eq) was then added and the mixture was stirred at -78 C. for 15 minutes and was then warmed to room temperature. The reaction was quenched with water (10 mL), diluted with EtOAc (600 mL) and was washed with water (100 mL), saturated aqueous NaCl, dried over MgSO4 and concentrated under reduced pressure. The recovered material was purified by silica gel chromatography (15-30% EtOAc:hexanes) to produce intermediate (1d) as a pale yellow oil (45 g).Intermediate (1d) (105.8 g, 303 mmol, 1.0 eq) was cooled at 0 C. in ice. TFA (300 mL) was added and the mixture was stirred at 0 C. for 15 minutes, then warmed to room temperature. After 90 minutes the mixture was concentrated under reduced pressure and redissolved in EtOAc (700 mL). The organic was washed with saturated bicarbonate (2×600 mL), saturated aqueous NaCl, dried over MgSO4, and concentrated under reduced pressure to produce a yellow solid. The material was suspended in hexanes (300 mL) and stirred at 0 C. for 30 minutes. The material was filtered and the solid was washed with cold hexanes (150 mL) to yield the title compound as a pale white solid (61.2 g). 1H-NMR (CDCl3) delta (ppm): 1.4 (m, 3H), 4.5 (m, 2H), 5.2 (s, 1H), 9.2 (d, 1H).

According to the analysis of related databases, 2034-22-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chao, Robert S.; Zhang, Weijiang; US2010/81697; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 760212-58-6, 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. 760212-58-6 name is 1-(4-Bromophenyl)-2-phenyl-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.

SYNTHESIS EXAMPLE 1 (Synthesis of Compound 1); Into a 100-mL three-necked flask, 3.0 g (8.6 mmol) of 1-(4-bromophenyl)-2-phenyl-1H-benzimidazole, 2.2 g (8.7 mmol) of bis(pinacolato)diboronic acid, 0.21 g (0.29 mmol) of [1,1′-bis(diphenylphosphino)ferrocene] dichloropalladium (II), 2.5 g (25 mmol) of potassium acetate, and 50 ml of DMF were charged and the mixture was heated at 80 C for 3 h in argon flow. After confirming the disappearance of the starting boron compound, the mixture was cooled to room temperature. After adding 2.2 g (8.6 mmol) of 9-bromophenanthrene, 0.21 g (0.29 mmol) of [1,1′-bis(diphenylphosphino)ferrocene] dichloropalladium (II), and 21 mL of a 2 M aqueous solution of sodium carbonate, the mixture was further heated at 80 C for 3 h under stirring. After the reaction, water was added. The precipitated crystals were corrected by filtration, washed with water and methanol, and dried under reduced pressure, to obtain a crude reaction product, which was then purified by a column chromatography (silica gel, dichloromethane: hexane), to obtain 2.5 g of white crystals. The obtained crystals were identified to Compound 1 by FD-MS (field desorption mass spectrometry). Yield: 65%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(4-Bromophenyl)-2-phenyl-1H-benzo[d]imidazole, and friends who are interested can also refer to it.

Reference:
Patent; Idemitsu Kosan Co., Ltd.; EP2236501; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem