Author: Jessica.F

Electric Literature of 71759-89-2, A common heterocyclic compound, 71759-89-2, name is 5-Iodo-1H-imidazole, molecular formula is C3H3IN2, 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.

Intermediate le 5-Iodo- l-(2,2,2-trifluoroethyl)- lH-imidazole In a 50 mL three-necked flask, 4-iodo-lH-imidazole (0.500 g, 2.58 mmol, Eq: 1.00) was combined under Ar with THF (7 ml) to give a colorless solution. Sodium hydride 55% (337 mg, 7.73 mmol, Eq: 3) was added at 0C (exothermic reaction, temperature rose to 17C). The reaction mixture was stirred at RT for 30 min. and then cooled down again to 0C, before 2,2,2-trifluoroethyl trifluoromethanesulfonate (1.2 g, 5.16 mmol, Eq: 2), dissolved in THF (3 ml), was added. The white suspension was stirred at RT for additional 1.5 hours when TLC indicated that the reaction was complete. Work up: The reaction mixture was poured into 10 mL H20 and extracted with EtOAc (2 x 15 mL). The organic layers were combined, washed with brine, dried over Na2S04, and concentrated i. V. Purification : The crude product was purified by flash chromatography (silica gel, 70 g, 0% to 60% EtOAc in heptane) to yield 80 mg of the desired title compound as off-white solid, besides 619 mg of the unwanted 4-iodo-l-(2,2,2-trifluoro-ethyl)-lH-imidazole. MS (ESI): 276.9 [M+H]+.

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; F. HOFFMANN-LA ROCHE AG; AEBI, Johannes; AMREIN, Kurt; HORNSPERGER, Benoit; KUHN, Bernd; MAERKI, Hans, P.; MAYWEG, Alexander, V.; MOHR, Peter; TAN, Xuefei; WO2013/120771; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 32673-41-9, 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 32673-41-9 as follows.

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. Chlorotriphenylmethane (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.; US2002/10184; (2002); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 57090-88-7,Some common heterocyclic compound, 57090-88-7, name is 1H-Imidazole-4-carbonitrile, molecular formula is C4H3N3, 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: A solution of 4-cyano-1H-imidazole (1000 mg, 10.74 mmol), 4-iodo -2-(trifluoromethyl)pyridine (3800 mg,14 mmol), (1R,2R)-N1,N2-dimethyl cyclohexane -1,2-diamine (150 mg, 1.07 mmol), CuI (200 mg, 1.07 mmol) and Cs2CO3 (7000 mg, 21.5 mmol) in 20 mL anhydrous DMF was stirred at 100 oC for 2 hours. The reaction mixture was cooled to room temperature and poured into 200 mL water. The mixture was extracted with ethyl acetate (80 mL*3). The organic layer were combined, washed by brine, dried by Na2SO4 and evaporated. The crude product was purified by silica flash column to afford compound 2 as white solid(1.5 g, 59percent yield).

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

Reference:
Article; Zheng, Qiangang; Chen, Ziqi; Wan, Huixin; Tang, Shuai; Ye, Yan; Xu, Yuan; Jiang, Lei; Ding, Jian; Geng, Meiyu; Huang, Min; Huang, Ying; Bioorganic and Medicinal Chemistry Letters; vol. 28; 23-24; (2018); p. 3808 – 3812;,
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 288-32-4 as follows. name: 1H-Imidazole

General procedure: General Procedure for Ultrasound-Promoted Iodination of Aromaticand Heteroaromatic Compounds: Hydrogen peroxide 30% (m/v) (4-8 mmol) was added to a suspension of theappropriate aromatic or heteroaromatic compound (1a-q) (2 mmol) and moleculariodine (2-4 mmol) in distilled water (10 mL). The mixture was sonicated and the progressof reaction was monitored by thin-layer chromatography (TLC). Afterward, asaturated sodium thiosulfate aqueous solution (10 mL) was added to the mixture,which was extracted with ethyl acetate (320mL). The organic phase was dried overMgSO4. After filtration, the solvent was evaporated under reduced pressure. The residuewas purified by column chromatography on silica gel using an appropriate eluent,affording the desired product (2a-q).

According to the analysis of related databases, 288-32-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ferreira, Irlon M.; Casagrande, Gleison A.; Pizzuti, Lucas; Raminelli, Cristiano; Synthetic Communications; vol. 44; 14; (2014); p. 2094 – 2102;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature 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.

Lithium hexamethyldisilazide (iM in tetrahydrofuran, 2i.4 ml, 2i.4 mmol) was added dropwise over iS mm to a stirred, cooled (-iO C) suspension of ethyl 4-methyl-i H25 imidazole-S-carboxylate (3.00 g, i9.S mmol) in dry dimethylformamide (200 ml) underan atmosphere of argon. After stirring for a further iO mi 0- (diphenylphosphoryl)hydroxylamine (5.45 g, 23.4 mmol) was added and the mixture was warmed to room temperature. After 6 h, water was added until a clearhomogeneous solution formed and subsequently the mixture was evaporated todryness. The resultant solid was treated with dichloromethane and the mixture wasfiltered and the filter cake was washed with further portions of dichloromethane. Thecombined filtrate and washings were evaporated to give a solid which was purified byflash chromatography (methanol-dichloromethane gradient, 0:100 rising to 5:95) togive 1.75 g (10.3 mmol, 53% yield) of the title compound as a white solid. Purity 100%.1H NMR (300 MHz, Chloroform-d) ppm 7.59 (s, 1H), 5.33 (br s, 2H), 4.37 (q, 2H, J =7.4 Hz), 2.46 (s, 3H), 1.40 (t, 3H, J = 7.4 Hz).UPLC/MS (3 mm) retention time 0.56 mm.LRMS: m/z 170 (M+1).

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

Reference:
Patent; ALMIRALL, S.A.; AIGUADE BOSCH, Jose; CONNOLLY, Stephen; EASTWOOD, Paul Robert; GOMEZ CASTILLO, Elena; MORENO MOLLO, Immaculada Montserrat; ROBERTS, Richard Spurring; SEVILLA GOMEZ, Sara; (216 pag.)WO2017/60488; (2017); 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. 3012-80-4, name is 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde

156.3 mg of the compound obtained in Synthesis Example 29-2 was dissolved in 2 ml of methanol, and then 2 ml of a 4 mol/l hydrochloric acid/dioxane was added to the solution, followed by stirring for 165 minutes at room temperature. On completion of the reaction, the solvent was distilled off. Subsequently, it was dissolved in 4 ml of anhydrous methanol, and then 131.1 mul of triethylamine and 62.8 mg of 1-methyl-2-formylbenzimidazole were added to the solution and the whole was stirred for 12 hours at room temperature. After the solvent was distilled off, subsequently, 4 ml of anhydrous methanol was added thereto and the whole was cooled to 0°C. Then, 19.8 mg of sodium borohydride was added to the solution and the whole was stirred for 30 minutes while being gradually returned to room temperature. On completion of the reaction, the solvent was distilled off and the residue was purified by means of silica gel column chromatography (10 g, chloroform/methanol = 10/1). After the resultant compound was dissolved in 2 ml of a 1 mol/l hydrochloric acid, water was distilled off. Consequently, 44.1mg of hydrochloride of the above-mentioned compound was obtained as a white-red solid product. MS(FAB,Pos.):m/z=642[M+1]+1H-NMR(500MHz,DMSO-d6):delta=1.73-1.91(4H,m),2.09(2H,br),3.64(3H,s ),3.85(3H,s),4.08-4.12(2H,m),4.38-4.43(2H,m),4.47-4.59(3H,m), 4.76-4.77(2H,m),5.98-5.99(1H,m),6.22-6.23(1H,m),6.79-6.80(1H, m),7.29-7.59(6H,m),7.60-7.73(2H,m),7.84-7.86(1H,m),7.94-8.08 (4H,m), 8.70-8.72 (2H,m), 8.96 (2H,br).

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 3012-80-4.

Reference:
Patent; Kureha Chemical Industry Co., Ltd.; EP1389460; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 1072-63-5, These common heterocyclic compound, 1072-63-5, name is 1-Vinyl-1H-imidazole, 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.

1-Vinylimidazole (5 g, 53.1 mmol) was taken in a 100-mL round-bottomedflask. To this, n-bromoethane (6.947 g, 63.7 mmol) was added andheated at 60 C for 3 h to produce 1-vinyl 3-ethylimidazolium bromide[ViEIm]Br in quantitative yields.

Statistics shows that 1-Vinyl-1H-imidazole is playing an increasingly important role. we look forward to future research findings about 1072-63-5.

Reference:
Article; Pothanagandhi, Nellepalli; Sivaramakrishna, Akella; Vijayakrishna, Kari; Reactive and functional polymers; vol. 106; (2016); p. 132 – 136;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 53439-88-6, These common heterocyclic compound, 53439-88-6, name is 5-Amino-1,3-dimethyl-1H-benzo[d]imidazol-2(3H)-one, 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.

To a 0 C. solution of 5-amino-1,3-dimethyl-1H-benzo[d]imidazol-2(3H)-one (4 g, 22.6 mmol) in 25 mL of CHCl3 and 25 mL of AcOH was slowly added dropwise bromine (3.5 g, 22.6 mmol). The mixture was stirred at RT for 30 min, then concentrated and purified by silica gel chromatography (1:1 EtOAc/hexanes) to afford 5-amino-6-bromo-1,3-dimethyl-1H-benzo[d]imidazol-2(3H)-one as a yellow solid (3.2 g, 69%). MS (ES+) C9H10BrN3O requires: 256. found: 257 [M+H]+.

The synthetic route of 53439-88-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Board of Regents, The University of Texas System; Palmer, Wylie; Jones, Philip; Liu, Gang; Petrocchi, Alessia; Reyna, Naphtali; Subrumanian, Govindan; Theroff, Jay; Yau, Anne; (114 pag.)US2016/60260; (2016); 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 147403-65-4 as follows. Application In Synthesis of Methyl 2-ethoxy-1-((2′-(N-hydroxycarbamimidoyl)-[1,1′-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate

Example 2Preparation of methyl l-[[2′-(4, 5-dihydro-5-oxo-4H-l, 2, 4-oxadiazol-3-yl) biphenyl- 4-yl] methyl]-2-ethoxy-lH-benzimidazole-7-carboxyIate To a solution of methyl 2-ethoxy [[2′-(hydroxyamidino) biphenyl-4-yl] methyl]- lH-benzimidazole-7-carboxylate (25 g) in tetrahydrofuran (700 ml), N,N- carbonyldi imidazole (15 g) and l,8-diazabicyclo[5.4.0]undec-7-ene (DBU)(13 g) was added and resulting solution was stirred for 30-40 mins. at about 20-25C. To the resulting solution ethyl acetate (700 ml) and saturated solution of sodium bisulphite (700 ml) was added. Organic layer was separated, washed with brine solution and evaporated under vacuum to concentrate the solution. Reaction mass was cooled to 20-25C and cyclohexane was added to it and the solution was stirred for about 20-25C. Product was filtered and dichloromethane was charged to it followed by stirring. The product was filtered, washed and dried to obtain title compound. (Yield: 17.8 g; 68% (Purity: 96% with desethyl impurity 0.1 1%)

According to the analysis of related databases, 147403-65-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JUBILANT LIFE SCIENCES LIMITED; BANSAL, Deepak; MISHRA, Himanchal; DUBEY, Shailendr, Kumar; CHOUDHARY, Alka, Srivastava; VIR, Dharam; AGARWAL, Ashutosh; WO2012/107814; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 68282-47-3, name is 2-Phenyl-1H-imidazole-4-carbaldehyde, 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 68282-47-3, Computed Properties of C10H8N2O

Reference Example 14 1-[(2,6-difluorophenyl)sulfonyl]-2-phenyl-1H-imidazole-4-carbaldehyde To a solution of 2-phenyl-1H-imidazole-4-carbaldehyde (1.00 g) in tetrahydrofuran (70 mL) was added sodium hydride (60% in oil, 348 mg) at room temperature, and the mixture was stirred for 30 min. 2,6-Difluorobenzenesulfonyl chloride (1.36 g) was added to the reaction mixture, and the mixture was stirred for 1.5 hr. Water was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was crystallized from diethyl ether to give the title compound as colorless crystals (yield 1.36 g, 67%). 1H-NMR (CDCl3) delta: 6.82-6.91 (2H, m), 7.27-7.46 (5H, m), 7.51-7.60 (1H, m), 8.38 (1H, s), 9.98 (1H, s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Phenyl-1H-imidazole-4-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2005957; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem