Author: Jessica.F

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

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

Synthetic Route of 760212-58-6, 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. 760212-58-6, name is 1-(4-Bromophenyl)-2-phenyl-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

1.0 g (2.9 mmol) of 1-(4-bromophenyl)-2-phenyl-1H-benzimidazole, 1.5 g (3.2 mmol) of 9,10-di(2-naphtyl)anthracene-2-boronic acid, and 0.067 g (0.058 mmol) of tetrakis(triphenylphosphine)palladium were dissolved into 20 mL of 1,2-dimethoxyethane. Then, 10 mL of a 2 M aqueous solution of sodium carbonate were added, and the whole was refluxed under heating for 8 hours in an argon atmosphere. After the completion of the reaction, the resultant was filtered, and the resultant solid was washed with water, methanol, and toluene to obtain 1.7g of a greenish white solid (84% yield) . Mass spectral analysis confirmed that the solid was a target product. The solid had an m/e of 698 with respect to a molecular weight of 698.27.

The synthetic route of 1-(4-Bromophenyl)-2-phenyl-1H-benzo[d]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IDEMITSU KOSAN CO., LTD.; EP1734038; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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 10040-98-9, A common heterocyclic compound, 10040-98-9, name is 4-Imidazol-1-yl-benzaldehyde, molecular formula is C10H8N2O, 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.

A mixture of malonitrile (60.0 mg, 0.9 mmol) and 4-(1H-imidazol-1-yl)benzaldehyde (155.0 mg, 0.9 mmol) in anhydrous ethanol ( 4.0 mL) was charged with N-methylmorpholine (0.1 mL, 0.9 mmol) for 2 minutes. To the mixture was added 3-benzyl-1-methyl-1H-pyrazol- 5(4H)-one (170.0 mg, 0.9 mmol) in one portion at room temperature. The reaction mixture was stirred at room temperature for 48 hrs. The suspension was filtered under vacuum and off white solid was obtained. The solid was gently washed with hexanes (20 mL) and chilled ethanol (10 mL) and further dried under high vacuum to provide compound 21 as an off white solid (330 mg, 89%).1H NMR (400 MHz, DMSO-d6) delta (ppm): 8.20 (s, 1H), 7.69 (s, 1H), 7.51 (d, J = 8.0 Hz, 2H), 7.21 (d, J = 8.0 Hz, 2H), 7.15-7.08 (m, 6H), 6.86 (d, J = 7.2 Hz, 2H), 4.46 (s, 1H), 3.66 (s, 3H), 3.53 (d, J = 15.2 Hz, 1H), 3.28 (s, 1H). MS (ESI): Calcd for C24H20N6O: 408, found: 409 (M+H)+.

The synthetic route of 10040-98-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NANTBIOSCIENCE, INC.; TAO, Chunlin; YU, Chengzhi; POLAT, Tulay; YAN, Chao; RABIZADEH, Shahrooz; THEODORESCU, Daniel; (108 pag.)WO2016/205460; (2016); 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. 36947-68-9, name is 2-Isopropyl-1H-imidazole, A new synthetic method of this compound is introduced below., Safety of 2-Isopropyl-1H-imidazole

To a stirred solution of 157 2-isopropyl-1H-imidazole (80.0 g, 0.73 mol) in 12 DMF (800 mL) at 0 C. was added 105 K2CO3(301 g, 2.2 mol) followed by 51 bromoacetonitrile (77 mL, 1.1 mol). Then the reaction mixture was allowed to stir at rt for 16 h. The mixture was diluted with EtOAc (800 mL) and water (1 L), the organic layer was separated and the aqueous layer was extracted with EtOAc (2×1 L). The combined organic extracts were dried over Na2SO4 and the solvent was removed by evaporation. Purification (FCC, SiO2, 30-40% EtOAc/hexanes) afforded the title compound (58.3 g, 54%) as a dark brown oil. 1H NMR (400 MHz, CDCl3) delta 7.00 (d, 1H, J=1.6 Hz), 6.94 (d, 1H, J=1.6 Hz), 4.89 (s, 2H), 3.05-3.01 (m, 1H), 1.37-1.35 (d, 6H, J=6.8 Hz).

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; Dart NeuroScience, LLC; Bookser, Brett; Botrous, Iriny; Branstetter, Bryan; Dyck, Brian; Weinhouse, Michael; US2019/177327; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 17325-26-7,Some common heterocyclic compound, 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, molecular formula is C5H6N2O2, 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 solution of methyl lH-imidazole-4-carboxylate (1.26 g, 10.0 mmol, 1.0 eq) in DMF (18.0 mL) was added K2C03 (3.5 g, 25.0 mmol, 2.5 eq), followed by 2- (trimethylsilyl)ethoxym ethyl chloride (2.3 mL, 13.0 mmol, 1.3 eq). The reaction mixture was stirred at 80 C for 12.0 h, then cooled and quenched by water (100.0 mL) and extracted with EA (50.0 mL X 2). The combined organic layers were dried over Na2S04, filtered and concentrated in vacuo. The resulting residue was purified by column chromatography (EA/PE=l/30, v/v) to provide methyl l-((2-(trimethylsilyl)ethoxy)methyl)-lH-imidazole-4- carboxylate (1.08 g, 42.5%).

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

Reference:
Patent; LIFESCI PHARMACEUTICALS, INC.; MCDONALD, Andrew; QIAN, Shawn; (346 pag.)WO2018/11628; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 137049-00-4, 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. 137049-00-4 name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, 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 144 (+-)-N-Benzyl-trans-3,4-dimethyl-4-(3-(1-methyl-1H-imidazole-4-sulfonylamino)phenyl)piperidine To a solution of (+-)4-(3-aminophenyl)-N-benzyl-trans-3,4-dimethylpiperidine (Preparation 9, 500 mg, 1.706 mmol) in pyridine (7 ml) under nitrogen was added 1-methyl-1H-imidazole-4-sulfonyl chloride (462 mg, 2.56 mmol), and the resultant mixture was stirred for 52 h before hydrolysing with ice (10 g). The reaction mixture was concentrated in vacuo at 80 C. and the residue was taken up in dichloromethane (200 ml), washed with saturated aqueous sodium hydrogen carbonate solution (70 ml), dried (Na2SO4), filtered and concentrated in vacuo to give the crude product. This was purified by silica (10 g) column chromatography eluding with ethyl acetate:triethylamine (99:1) to give the title compound as a white solid (640 mg, 86%). NMR (CDCl3, selected data for the free base): 0.5 (d, 3H), 1.1 (s, 3H), 3.6 (s, 3H), 6.8-7.4 (m, 11H). MS (thermospray): M/Z [MH+] 439.1; C24H30N4O2S+H requires 439.2.

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

Reference:
Patent; Armer, Richard Edward; Dutton, Christopher James; Gethin, David Morris; Gibson, Stephen Paul; Smith, Julian Duncan; Tommasini, Ivan; US2003/78282; (2003); 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. 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, A new synthetic method of this compound is introduced below., COA of Formula: C4H6N2S

General procedure: Difluoromethylation of Heterocycles Standard Procedures: Procedure B: To a solution of heterocycle (0.25 mmol, 1.0 equiv) and zinc difluoromethanesulfinate (DFMS) (173 mg, 0.50 mmol, 2.0 equiv ?calculated as anhydrous?) in dichloromethane (1.0 mL) and water (0.4 rnL) at room temperature was added trifluoroacetic acid (20 muL, 0.25 rnmol, 1.0 equiv) followed by slow addition of tert-butyl hydroperoxide (70% solution in water, 0.1 mL, 0.75 mmol, 3.0 equiv) with vigorous stirring. The reaction was monitored by thin layer chromatography until completion. For substrates which do not go to completion in 24 hours, a second addition of DFMS (2.0 equiv) and tert-butyl hydroperoxide (3.0 equiv) may be added to drive the reaction further. Upon consumption of starting material, the reaction was partitioned between dichioromethane (2.0 mL) and saturated sodium bicarbonate (2.0 mL) . The organic layer was separated, and the aqueous layer was extracted with dichioromethane (3 X 2.0 mL) . The organic layers were dried with sodium sulfate, concentrated and purified by column chromatography on silica gel. If substrates are less reactive, alpha,alpha,-trifluorotoluene can be substituted for DCM, as it causes improved reactivity for some cases. For water-soluble starting materials, a purely aqueous reaction (1.0 mL of water) can be run and in some cases, it was also found to display improved reactivity. In lieu of a workup, these reactions can be concentrated and the product purified directly. If the addition of tert-butyl hydroperoxide is performed too rapidly, the resulting exotherm can result in reduced yield and selectivity. This is especially important on larger scales (see gram scale procedure: substrate 2), where a syringe pump can be used to meter in tert-butyl hydroperoxide.It is noted that trifluoroacetic acid (TFA) is not required in either of the above procedures. It was also found that TFA showed improved rate and conversion for selected nitrogen heteroarene substrates, but was not essential to achieve the desired reactivity for most cases. When present, TFA is typically used at about 0.25 to about 2 equivalents per equivalent of nitrogen heteroarene, and more preferably at about 0.5 to about 1.5 equivalents relative to the nitrogen heteroarene.

The synthetic route of 60-56-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE SCRIPPS RESEARCH INSTITUTE; BARAN, Phil, S.; DIXON, Janice, Akemi; BAXTER, Ryan; FUJIWARA, Yuta; WO2013/82028; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 3034-42-2, These common heterocyclic compound, 3034-42-2, name is 1-Methyl-5-nitroimidazole, 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: A solution of complex 4a (1 g, 4.25 mmol) in benzene (10 ml) was stirred at 15-20 and treated with a solution of heterocyclic amine or oxaadamantane () (4.25 mmol) in benzene (5 ml) (Scheme 10, Table 1). The reaction mixture was stirred for the indicated time at room temperature, with periodic control of the amount of evolved THF by GLC (60-70, adsorbent – chromosorb, liquid phase – PEG monolaurate). After the increase of THF signal stopped, the reaction mixture was evaporated from Petri dish under exaust hood, the residue was extracted first with hexane and then with Et2O. The combined extract was evaporated under vacuum at room temperature, the residue was recrystallized from Et2O-hexane mixture. Complexes of trinitromethylborane with amines (compounds 7-s) or with oxaadamantanes (compounds 4d,e) were thus obtainecharacteristics, as well as yields and melting points of target complexes 4d,e and 7-s are given in Table 1

The synthetic route of 3034-42-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shitov; Tartakovskii; Ioffe; Chemistry of Heterocyclic Compounds; vol. 50; 12; (2015); p. 1647 – 1657; Khim. Geterotsikl. Soedin.; vol. 50; 12; (2014); p. 1795 – 1806,12;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem