Category: 3034-50-2

Synthetic Route of 3034-50-2, A common heterocyclic compound, 3034-50-2, name is Imidazole-4-carbaldehyde, molecular formula is C4H4N2O, 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 1L three-necked round-bottomed flask with an addition funnel was added 3H-imidazole-4-carbaldehyde (4, 12 g, 0.125 mol) trityl chloride (38.3 g, 0.137 mol) and acetonitrile (400 mL). The mixture was stirred at rt to give a slurry. Triethylamine (30 mL, 0.215 mol) was added drop wise over 20 min. After the addition was complete, the reaction mixture was stirred at rt for 20 h. Hexane (40 mL) and water (400mL) were added. The slurry was stirred for 30 min and filtered. The cake was washed with water (3 × 100 mL) and dried in a vacuum oven at 50 C for 20 h to give 5 as a white solid (39.8 g, 94%).

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:
Article; Suryadevara, Praveen Kumar; Racherla, Kishore Kumar; Olepu, Srinivas; Norcross, Neil R.; Tatipaka, Hari Babu; Arif, Jennifer A.; Planer, Joseph D.; Lepesheva, Galina I.; Verlinde, Christophe L.M.J.; Buckner, Frederick S.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry Letters; vol. 23; 23; (2013); p. 6492 – 6499;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 3034-50-2,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.

A. 1-Trityl-4-carboxaldehyde-1H-imidazole (cas No.33016-47-6) According to procedure outlined in J. Med. Chem. 2002, 45(1), 177, to imidazole-4-carboxaldehyde (15.0 g, 156.2 mmol) in DMF (300 mL) is added triethylamine (43.8 ml, 312 mmol) followed by trityl chloride (44.4 g, 159.0 mmol). The reaction mixture is stirred at ambient temperature for 18 h before the solvent is removed in vacuo. The resulting solid is dissolved in dichloromethane and washed with sodium bicarbonate and water. The organic phase is concentrated in vacuo to give the desired material as a solid.

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

Reference:
Patent; Ksander, Gary Michael; Meredith, Erik; Monovich, Lauren G.; Papillon, Julien; Firooznia, Fariborz; Hu, Qi-Ying; US2007/49616; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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

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 3034-50-2 as follows. Application In Synthesis of Imidazole-4-carbaldehyde

Example 63; (3H-Imidazol-4-ylmethyl)-(2-methoxy-phenyl)-amine; To a solution of 2-methoxyaniline (0.62 g, 5 mmol) in methanol (5 ml) was added 4- formylimidazole (0.48 g, 5 mmol). After stirring the mixture overnight at 600C the solution was cooled and sodium borohydride (0.28 g, 7.5 mmol) were added. The reaction mixture was stirred at room temperature for 4 hours. Then water was added and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with water, dried over magnesium sulfate and evaporated. The residue was purified by recrystallisation from heptane/ethyl acetate to yield off-white crystals (0.85 mg, 84%); MS (ISP): 204.3 ((M+H)+’).

According to the analysis of related databases, 3034-50-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2008/46757; (2008); 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. 3034-50-2, name is Imidazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., category: imidazoles-derivatives

First, 4-imidazole formaldehyde (1a, 960 mg, 10 mmol) was added to the reaction flask.Place in an ice water bath. After 10 min, triethylamine (TEA) (278 mul, 2.0 mmol) was added to the reaction flask, and the mixture was stirred in the ice water bath for 5 min.Di-tert-butyl dicarbonate (2.4 g, 1.0 mmol) was then added to the reaction flask, and the reaction was moved to room temperature to react overnight.After the reaction was detected to be complete by TLC, the solvent was spin-dried and alumina column chromatography (PE: EA = 2: 1) was used to obtain intermediate 1b.

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 3034-50-2.

Reference:
Patent; Xihua University; Yang Lingling; Wang Zhouyu; Qian Shan; Li Ling; Xu Wei; Yang Huan; Liu Siyan; Yao Hao; Yan Jie; Li Chao; (21 pag.)CN110294713; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 3034-50-2, name is Imidazole-4-carbaldehyde, 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. Computed Properties of C4H4N2O

Preparation 5 1-Trityl-1H-imidazole-4-carboxaldehyde A solution of trityl chloride (9.5 g, 34.3 mmol) in N,N-dimethylformamide (50 ml) was added dropwise to an ice-cooled solution of imidazole-4-carboxaldehyde (3 g, 31.2 mmol) and triethylamine (17 ml, 125 mmol) in N,N-dimethylformamide (30 ml) and the solution was stirred for 2 hours. The reaction was then allowed to warm to room temperature, and was stirred for a further 18 hours. Water (200 ml) was added, and the resulting pink solid was collected and dried, then dissolved in dichloromethane (200 ml). The resulting solution was washed with water (2*100 ml), dried (MgSO4) and evaporated under reduced pressure. The product was recrystallized from ethanol to afford the title compound as a solid, 7.8 g. 1H-NMR (CDCl3, 400 MHz) delta: 7.06 (m, 6H), 7.32 (m, 9H), 7.48 (s, 1H), 7.58 (s, 1H), 9.82 (s, 1H). Microanalysis found: C, 81.54; H, 5.37; N, 8.24. C23H18N2O requires C, 81.63; H, 5.36; N, 8.28%.

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

Reference:
Patent; Pfizer Inc.; US2003/199522; (2003); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 3034-50-2, The chemical industry reduces the impact on the environment during synthesis 3034-50-2, name is Imidazole-4-carbaldehyde, I believe this compound will play a more active role in future production and life.

A 1 litre flask was charged with 1 H-imidazole-4-carbaldehyde (14 g, 146 mmol) and absolute ethanol (240 mL). Then 2-(benzylamino)ethanol (20.8 mL, 146 mmol) wasadded and the white suspension turned slowly into a yellow solution after 3 h The mixture was then cooled in an ice-bath and sodium triacetoxyborohydride (93 g, 437 mmol) was added portionwise. The mixture was then stirred overnight at room temperature. Water was added and the mixture was partially concentrated. After neutralising to pH -7 with 1 M aqueous NaOH, the aqueous phase was rinsed twicewith ethyl acetate, then it was basified further to pH 14. The aqueous layer was then extracted with thrice with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and evaporated to dryness to give the title compound (26.9 g), which was directly used in the next step.1H NMR (ODd3) 67.52 (s, 1H), 7.37-7.18 (m, 6H), 6.87 (s, 1H), 3.69 (s, 2H), 3.68- 3.58 (m, 5H), 2.70 (t, J = 5.1 Hz, 2H).LC/MS: m/z 232 [M+H].

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, Imidazole-4-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LABORATORIOS DEL DR. ESTEVE S.A.; DIAZ-FERNANDEZ, Jose Luis; ALMANSA-ROSALES, Carmen; NIECZYPOR, Piotr; WO2015/91795; (2015); A1;,
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. 3034-50-2, name is Imidazole-4-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C4H4N2O

To a mixture of 1H-imidazole-4-carbaldehyde (3.71 g, 38.6 mmol), 1-chloro-4-iodobenzene(13.81 g, 57.9 mmol), (1R,2R)-N1,N2-dimethylcyclohexane-1,2-diamine (1.10 g, 7.72 mmol),copper(l) iodide (0.368 g, 1.93 mmol) and cesium carbonate (25.2 g, 77 mmol) was added DMF (50 mL). The reaction was sealed and heated to 110 00 for 18 hours. The reaction mixture was then cooled to room temperature and diluted with a saturated solution of NH4CI.brown solid develops. Solid was collected, washed with water and air dried. Solid materialwas then dissolved in 10%MeOH:90%DCM solution and dried (Na2504), filtered and concentrated to afford a dark brown solid 1-(4-chlorophenyl)-1 H-imidazole-4-carbaldehyde (8.55 g, 41.4 mmol, 107 % yield). Material as used without further purification. LCMS m/z 207.1 (M + H), Rt 0.58 mm.Step 1

The synthetic route of 3034-50-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; CAFERRO, Thomas Raymond; CHEN, Zhuoliang; CHO, Young Shin; COSTALES, Abran Q.; LEVELL, Julian Roy; LIU, Gang; MANNING, James R.; SENDZIK, Martin; SHAFER, Cynthia; SHULTZ, Michael David; SUTTON, James; WANG, Yaping; ZHAO, Qian; WO2014/141104; (2014); A1;,
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. 3034-50-2, name is Imidazole-4-carbaldehyde, A new synthetic method of this compound is introduced below., Computed Properties of C4H4N2O

Synthesis of 1-Trityl-1H-imidazole-4-carbaldehyde STR49 To dimethylformamide (100 mL) was added imidazole-4-carboxaldehyde (10 g, 0.104 mol, Aldrich Chemical Corp.) and triethylamine (20.5 mL, 0.147 mol). A solution of trityl chloride (40 g, 0.143 mol) in dimethylformamide (300 mL) was added, followed by stirring at 25 C. for 6 hours. The solvent was removed in vacuo, and the residue was dissolved in ethyl acetate (1.5 L) and 1N citric acid (350 mL). The phases were separated, and the organic phase was washed with brine, dried over anhydrous magnesium sulfate, and filtered. Concentration of the solution in vacuo gave a white solid, 27.59 g, 78% yield. NMR was consistent with structure. MS: APCI: M-1: 337.2 (M: 338.41).

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; Warner-Lambert Company; US6143766; (2000); A;,
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. 3034-50-2, name is Imidazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., Safety of Imidazole-4-carbaldehyde

Example 72An alternate method’for the synthesis of the imidazole intermediate is described below:4-Cyano-l-(2-trimethylsilanyl-ethoxymethyl)-lH-imidazole-2-carboxylic acid potassium salt a) lH-Imidazole-4-carbonitrile; ‘-NHA 22-L, four-neck, round-bottom flask equipped with a mechanical stirrer, a temperature probe, a condenser, and an addition funnel with a nitrogen inlet was charged with lH-imidazole-4-carboxaldehyde (Aldrich, 1.10 kg, 11.5 mol) and pyridine (3.0 L, 3.0 mol). The reaction flask was cooled to 8 0C with an ice bath and hydroxylamine hydrochloride (871 g, 12.5 mol) was added slowly in portions to maintain the internal temperature below 30 °C. The reaction was allowed to cool to ambient temperature and stirred for 2 h at ambient temperature. The resulting thick yellow solution was heated to 80 0C with a heating mantle and acetic anhydride (2.04 L, 21.6 mol) was added dropwise EPO over 200 min to maintain the temperature below 110 °C during the addition. The reaction mixture was heated at 100 0C for 30 min, after which time it was allowed to cool to ambient temperature and then further cooled in an ice bath. The pH was adjusted to 8.0 (pH meter) by the addition of 25 wt percent NaOH (5.5 L) at such a rate that the internal temperature was maintained below 30 °C. The reaction mixture was then transferred into a 22-L separatory funnel and extracted with ethyl acetate (6.0 L). The combined organic layer was washed with brine (2 x 4.0 L), dried over MgSO4, filtered, and concentrated to dryness under reduced pressure at 35 °C to give the crude product as a yellow semisolid. The resulting semisolid was suspended in toluene (3.0 L) and stirred for 1 h, after which time it was filtered to give a light yellow solid, which was resuspended in toluene (3.0 L) and stirred for 1 h. The resulting slurry was filtered and the filter cake washed with toluene (2 x 500 mL) to give the title compound as a light yellow solid [870 g, 82percent). The 1H and 13C NMR spectra were consistent with the assigned structure.

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 3034-50-2.

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2006/47504; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem