Category: imidazoles-derivatives

Reference of 5805-57-2, These common heterocyclic compound, 5805-57-2, name is (1H-Benzo[d]imidazol-2-yl)methanamine, 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.

General procedure: 9-Chloroacridine or its derivatives (1.0 mmol) and phenol (10.0 mmol) were added into a 100 ml round-bottom flask and the mixture was stirred for 1 h at 60 C under argon atmosphere. Then benzimidazole derivatives (8a-8n, 8p-8q, 1.2 mmol) were added. The mixture was stirred under 120 C for 2 h. Then the mixture was poured into a mixture of ethyl acetate (50 mL) and N-methyl morpholine (1 ml) to get the crude product as yellow precipitation. The crude product was recrystallized from ethylacetate.

The synthetic route of 5805-57-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gao, Chunmei; Li, Bin; Zhang, Bin; Sun, Qinsheng; Li, Lulu; Li, Xi; Chen, Changjun; Tan, Chunyan; Liu, Hongxia; Jiang, Yuyang; Bioorganic and Medicinal Chemistry; vol. 23; 8; (2015); p. 1800 – 1807;,
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

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. 288-32-4, name is 1H-Imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C3H4N2

The 1-(4-vinylbenzyl)imidazole was prepared by the reported procedure[27]by heating 4-vinylbenzylchloride (1.0 equivalent) and imidazole (4.0 equivalent) in acetone:water (1:1, 10 volume) with sodium bicarbonate (1.25 equivalent) at 50 C for 20 h. It was characterised by FT-IR and1H-NMR.The mixture of 1-(4-vinylbenzyl)imidazole (32.7 mmol), DVB and azobisisobutyronitrile (AIBN, 5 mol %) in acetonitrile (50 mL) was taken in a round bottom flask. The flask was heated to 80 C in an oil bath and the temperature was maintained for 8 h. The solid product obtained by filtration, was washed with acetonitrile (3 X 20 mL) and dried in an oven at 100 C. Thus, using 3, 5, and 7 mol% of DVB the catalysts CPVBIm-3, CPVBIm-5 and CPVBIm-7, respectively were prepared.

The synthetic route of 288-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Korgavkar, Nilesh N.; Samant, Shriniwas D.; Synthetic Communications; vol. 48; 4; (2018); p. 387 – 394;,
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. 26663-77-4, name is Methyl benzimidazole-5-carboxylate, A new synthetic method of this compound is introduced below., Computed Properties of C9H8N2O2

Compound 15 (0.5 g, 2.84 mmol) was reacted with 4-phenylbutylbromide (0.5 mL, 2.84 mmol) in anhydrous DMF(10 mL) and K2CO3 (0.79 g, 5.68 mmol) was added slowly at 0C.The resulting reaction mixture was warmed to 60C and stirredfor 2 h. After completion, reaction mixture was quenched withsaturated NH4Cl, and extracted with ethyl acetate (250 mL). Thecombined organic layers were washed with brine, dried overanhydrous Na2SO4, and concentrated in vacuo. The crude residuewas purified over silica gel column chromatography (MeOH/DCM= 1:49) to yield the mixture of isomers 16 (0.79 g, 90%) as acolorless liquid.Spectral data for isomers. 1H NMR (CDCl3, 300 MHz); delta8.53 (s, 1H), 8.10 (t, 2H, J= 6.0 Hz), 7.34-7.29 (m, 3H), 7.16-7.14(m, 3H), 4.23-3.94 (m, 2H), 2.68-2.63 (m, 2H), 2.30-2.20 (m, 2H).13C NMR (CDCl3, 75 MHz): 167.7, 147.3, 144.6, 139.9, 133.4,128.7, 126.5, 124.8, 123.5, 122.8, 120.1, 112.1, 52.2, 44.5, 32.6,30.9.

The synthetic route of 26663-77-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Srinivasrao, Ganipisetti; Park, Jung-Eun; Kim, Sungmin; Ahn, Mija; Cheong, Chaejoon; Nam, Ky-Youb; Gunasekaran, Pethaiah; Hwang, Eunha; Kim, Nam-Hyung; Shin, Song Yub; Lee, Kyung S.; Ryu, Eunkyung; Bang, Jeong Kyu; PLoS ONE; vol. 9; 9; (2014);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 152628-03-0, 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. 152628-03-0, name is 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Reference Example A3: 4-Methyl-6-(2-oxazolyl)-2-propylbenzimidazole [step 1] 6-Methoxycarbonyl-4-methyl-2-propylbenzimidazole (EP502314; 500 mg, 2.29 mmol) was suspended in ethanol (15 mL), 4 mol/L aqueous sodium hydroxide solution (3.1 mL) was added, and the mixture was stirred under reflux for 7 hr. The mixture was concentrated under reduced pressure, and water (20 mL) was added. Under ice-cooling, the mixture was adjusted to pH 1 with 2 mol/L hydrochloric acid, and extracted with chloroform. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was dissolved in dichloromethane, aminoacetaldehyde dimethylacetal (0.50 mL, 4.58 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (527 mg, 2.75 mmol) and 1-hydroxybenzotriazole (421 mg, 2.75 mmol) were added, and the mixture was stirred at room temperature for 6 hr. To the mixture were added saturated aqueous sodium hydrogen carbonate solution (100 mL) and chloroform (100 mL), and the organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give 6-(2,2-dimethoxyethylcarbamoyl)-4-methyl-2-propylbenzimidazole. ESI-MS m/z; 306 (M + H)+; 1H-NMR (CDCl3, delta): 1.02 (t, J = 7.3 Hz, 3H), 1.82-1.97 (m, 2H), 2.65 (s, 3H), 2.92 (t, J= 7.3 Hz, 2H), 3.45 (s, 6H), 3.64 (t, J = 5.3 Hz, 2H), 4.52 (t, J = 5.3 Hz, 1H), 6.42 (s, 1H), 7.89 (s, 1H).

The synthetic route of 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kyowa Hakko Kirin Co., Ltd.; EP2327690; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 5805-57-2, name is (1H-Benzo[d]imidazol-2-yl)methanamine, 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. HPLC of Formula: C8H9N3

General procedure: Starting amino compound (0.238 mmol) was dissolved in THF (25 mL) and triethylamine (10 drops) was added to the stirred solution. Acyl halide (0.149 mmol) was added dropwise to the stirred solution, which was then heated under reflux for 3h. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in EtOAc and washed with aq. K2CO3 solution followed by brine. The organic layer was then dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 1-5 methanol/DCM v/v.

The synthetic route of (1H-Benzo[d]imidazol-2-yl)methanamine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Elshihawy, Hosam; Helal, Mohamed A.; Said, Mohamed; Hammad, Mohamed A.; Bioorganic and Medicinal Chemistry; vol. 22; 1; (2014); p. 550 – 558;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 124750-92-1, These common heterocyclic compound, 124750-92-1, name is Losartan carboxylic acid, 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.

Step B: 2-butyl-4-chloro-l-{[2′-(2-trityl-2H-tetrazol-5-yl)biphenyl-4-yl]methyl}-lH-imidazole-5- carboxylic acid To a solution of E3174 (234.58 g, 0.54 mol) in DCM (4500 niL) was added triethylamine (85 niL, 0.59 mol) followed by a solution of trityl chloride (159 g, 0.56 mol) in DCM (800 mL) and the reaction mixture was stirred at rt overnight. The reaction mixture was washed with water, dried (MgSO4), filtered, and concentrated under reduced pressure. Chromatography over silica gel eluting with acetone/heptane 20:80% afforded the title compound as an orange solid.

The synthetic route of 124750-92-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NICOX S.A.; WO2009/150007; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 36947-68-9, 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. 36947-68-9 name is 2-Isopropyl-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.

A mixture of Example 29b (1.3 g, 6.8 mmol), 2-isopropyl-lH-imidazole (0.9 g, 8.2 mmol), CuBr (0.14g, 1.0 mmol), L-proline (0.12g, l .Ommol) and Cs2C03 (4.3 g, 13.6 mmol) was stirred in 40 mL toluene under reflux with the protection of nitrogen for 16 hrs. The solvent was then removed under vacuum, the residue was then washed by water (35 mL), extracted with EtOAc (55 mL) twice, the organic phase was combined, washed with brine, dried over Na2S04, and concentrated under vacuum to give brown oil, which was further purified by combined-flash (EA / PE =70%-95%) to give the desired product Example 29c (120 mg, yield 9%) as yellow solid. LCMS [M+1]+=220.1

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

Reference:
Patent; FRONTHERA U.S. PHARMACEUTICALS LLC; JIN, Bohan; DONG, Qing; HUNG, Gene; (212 pag.)WO2017/218960; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 693-98-1,Some common heterocyclic compound, 693-98-1, name is 2-Methyl-1H-imidazole, molecular formula is C4H6N2, 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.

2-methyl-imidazole is reacted with a molar equivalent of acrylonitrile in a mixture of triethylamine and toluene. The mixture is heated at 50 C. to generate an intermediate imidazole compound linked to acrylonitrile, N-propanenitrile-2-methyl-imidazole. The nitrile bond is reduced by bubbling hydrogen gas into a solution of N-propanenitrile-2-methyl-imidazole in methanol catalyzed by Rainey Nickel. N-propylamine-2-imidazole is generated from the reduction reaction as seen in Scheme I.

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

Reference:
Patent; THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ALABAMA; Bara, Jason Edward; (17 pag.)US2018/21723; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 51605-32-4,Some common heterocyclic compound, 51605-32-4, name is Ethyl 5-methyl-1H-imidazole-4-carboxylate, molecular formula is C7H10N2O2, 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.

Step 1 To a stirred suspension of 5.4 g ethyl 4-methyl-5-imidazolecarboxylate in 30 ml tetrahydrofuran were added 1.4 g sodium hydride in mineral oil (60percent) in portions at ambient temperature under argon atmosphere. After gas formation ceased, 2.24 ml methyl iodide were added dropwise at 0° C., then the mixture was stirred at ambient temperature overnight. The precipitate was filtered off and the filtrate was concentrated. The resulting residue was purified by column chromatography eluted with dichloromethane:methanol (100:0->87:13) to give pure intermediate I.4. Yield: 1.0 g of 1.4 (17percent of theory) Analysis: [M+H]+=169; HPLC-MS (method G): Rt=0.76 min

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 5-methyl-1H-imidazole-4-carboxylate, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; DAHMANN, Georg; DOLLINGER, Horst; GNAMM, Christian; FIEGEN, Dennis; HOFFMANN, Matthias; KLICIC, Jasna; LAMB, David James; SCHNAPP, Andreas; US2013/281430; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem