Month: April 2021

These common heterocyclic compound, 31722-49-3, name is 1H-Imidazole-2-carbonitrile, 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. Safety of 1H-Imidazole-2-carbonitrile

6.7. Synthesis of aR,2S,3R)-l-aH,l’H-2,2′-biimidazol-5-yl)butane-l,2,3,4- tetraolThe captioned compound was prepared by General Method B with the following alterations. To a solution of lH-imidazole-2-carbonitrile (0.39 g, 4.17 mmol) in methanol (4.8 ml) was added a solution of sodium methoxide in methanol (25 wt%, 0.54 g, 0.57 ml, 2.50 mmol), stirred for 16 h and compound 8 (0.964 g, 4.17 mmol) was added in 10 ml of MeOH. A precipitate formed and was filtered and washed with acetone (15 ml). The filtrate was concentrated to dryness, and was purified by preparative HPLC (10 mM aq ammonium acetate/acetonitrile) to give the title compound (0.0141 g, 0.0554 mmol) as an off-white solid. MS m/z Ci0Hi4N4O4 [M + H] + = 255; 1H NMR (400 MHz, CD3OD) delta 3.56-3.57 (m, 2H), 3.67-3.74 (m, 2H), 4.90 (s, IH), 7.04 (s, IH).

The synthetic route of 1H-Imidazole-2-carbonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LEXICON PHARMACEUTICALS, INC.; WO2008/109314; (2008); 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. 124750-59-0, name is 2-Propyl-1H-imidazole-4,5-dicarboxylic acid dimethyl ester belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 2-Propyl-1H-imidazole-4,5-dicarboxylic acid dimethyl ester

A mixture of dimethyl-2-propylimidazole-4,5-dicarboxylate compound of formula-2a (100 grams), 4-[2-(trityltetrazol-5-yl)phenyl]benzyl bromide compound of formula-3 (296 grams), potassium carbonate (119 grams) in dimethyl formamide (100 ml) and acetone (500 ml) was heated to reflux temperature. The reaction mixture was stirred up to reaction completion and solvent was distilled off completely from the reaction mixture under reduced pressure at below 50C. The reaction mixture was cooled to 25-300C, acetone (150 ml) and water (1000 ml) were added to it then stirred for 60 minutes. The obtained solid was filtered, washed with water and then the wet solid was recrystallized from acetone to provide the title compound.Yield: 285 grams;Purity by HPLC: 98.15%

The synthetic route of 124750-59-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MSN LABORATORIES LIMITED; SATYANARAYANA REDDY, Manne; NAGARAJU, Chakilam; THIRUMALAI RAJAN, Srinivasan; KODANDA RAMPRASAD, Achampeta; RAMA SUBBA REDDY, Karamala; WO2011/21224; (2011); A2;,
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. 1003-91-4, name is 2,4,5-Tribromo-1-methylimidazole, A new synthetic method of this compound is introduced below., Computed Properties of C4H3Br3N2

2,4,5-tribromo-1-methyl-imidazole (1) (0.5g, 1.56mmol) and trimethyloxonium tetrafluoroborate (0.25g, 1.72mmol) in a Schlenk flask was charged with dichloromethane (30mL). The mixture was stirred overnight at room temperature to afford a colorless solid. The volatiles were removed in vacuum and the resulted solid was washed with diethyl ether (2¡Á15mL) and dried under vacuum to give 3 as colorless powder. Yield: 0.60g (91%). Mp: 304C. 1H NMR (DMSO-d6, 500MHz, delta, ppm): 3.78 (s, 6H, N-CH3). 13C NMR (DMSO-d6, 125MHz, delta, ppm): 38.1 (N-CH3), 112.0 (4,5-C-Br), 124.9 (C2-Br). IR (KBr, cm-1): 1637(m), 1554(m), 1504(s), 1445(m), 1396(m), 1329(m), 1295(m), 1056(vs), 1034(vs), 813(w), 641(w), 522(w). ESI MS: m/z 332.8081 [M-(BF4) ]+.

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; Avinash, Iruthayaraj; Gupta, Vivek; Karthik, Vedhagiri; Anantharaman, Ganapathi; Journal of Organometallic Chemistry; vol. 851; (2017); p. 104 – 114;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 24134-09-6, name is 5-Bromo-1,2-dimethyl-1H-imidazole, 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 24134-09-6, Quality Control of 5-Bromo-1,2-dimethyl-1H-imidazole

Example 42a: (4-chloro-2-methoxy-3-((6-(trifluoromethyl)pyridin-3-yl)methyl)quinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)(2,6-dimethylpyridin-3-yl)methanol A solution of -BuLi (2.5 M in liexanes, 1.2 mL, 3.0 mmol) was added dropwise by syringe to a solution of 5-bromo- 1 ,2-dimethyl- lH-imidazole (570.8 mg, 3.261 mmol) in dry THF (6 mL) in a dry ice-acetone bath. After 1-2 minutes, a solution of (4-chloro~2~methoxy-3-((6- (frifluoromethyl)pyridin-3-yl)m (0.790 g, 1 .626 mmol, Intermediate 47: step b) in dry THF (2 mL) was added dropwise. The reaction was stirred for 5 minutes, then was moved into an ice bath and allowed to warm to ambient temperature. The reactio was quenched with saturated aqueous ammonium chloride. The mixture was partitioned between water and dichloromethane. The separated aqueous phase was further extracted with dichloromethane. The organic phase was dried (Na2S04), filtered, and concentrated. The crude product was purified by flash column chromatography (silica gel, 0-5% MeOH-DCM) followed by reverse-phase HPLC (acetonitrile/H20 + 0.05% TFA). The product fractions were basified with saturated aqueous sodium bicarbonate and extracted with DCM, before being dried (Na2S04), filtered, and concentrated to dryness to provide the title compound. H NMR. (400 MHz, CDC13) delta 8.76 (d, J = 2.0 Hz, 1H), 8.13 (d, J = 2.2 Hz, 1H), 7.79 – 7.73 (m, 2H), 7.57 (dd, J = 8.1, 0.9 Hz, 1H), 7.41 (dd, J = 8.7, 2.2 Hz, 1H), 7.1 1 (d, J = 8.0 Hz, 1H), 6.94 (d, J = 8.0 Hz, i f }. 6.04 (s, 1H), 4.35 (s, 2H), 4.08 (s, 3H), 3.39 (s, 3H), 2.53 (s, 3H), 2.41 (s, 3H), 2.37 (s, 3H); MS m/e 582.2 [M+H]+.Example 42a was purified by chira SFC (ChiralPak AD-H, 70:30 C02:mixture of MeOH/?PrOH (50:50 + 0.3% PrNH2)) to provide two pure enantiomers. The first eluting enantiomer was Example 42b: H NMR (400 MHz, CDCI3) delta ppm 8.77 (s, 1H), 8.15 – 8.52 (m, I I I). 7.77 (d, ,/ 8.3 Hz, 2H), 7.57 (d, ./ 8.2 Hz, 1 H), 7.45 – 7.40 (rn, 1H), 7.1 1 (d, J = 8.0 Hz, I I I). 6.94 (d, ./ = 8.1 Hz, I I I). 6.06 (s, 1 1 1). 4.36 (s, 2H), 4.09 (s, 3H), 3.40 (s, 3H), 3.30 (s, IH), 2.54 (s, 3H), 2.42 (s, 3H), 2.39 (s, 3H); MS m/e 582.2 [M+H]+. The second eluting enantiomer was Example 42c: 1 I NMR (400 MHz, CDCI3) 6 ppm 8.76 (d, ,/ 2.1 Hz, l i s). 8.56 (d, ./ 2,1 Hz, 1H), 7.79 – 7.74 (rn, 1H), 7.70 (d, J = 8.7 Hz, 5 H), 7.60 – 7.55 (m, I H), 7.37 (dd, J= 8.7, 2.1 Hz, IH), 7.1 1 (d, ./ 8.0 Hz, IH), 6.93 (d, ./ = 8.0 Hz, IH), 5.98 (s, IH), 4.35 is. 21 1). 4.28 – 4.18 (m, IH), 4.07 (s, 3H), 3.37 (s, 3H), 2.53 (s, 3H), 2.40 (s, 3H), 2.33 (s, 3H); MS m/e 582.0 [M+Hf .

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, 5-Bromo-1,2-dimethyl-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; LEONARD, Kristi A.; BARBAY, Kent; EDWARDS, James P.; KREUTTER, Kevin D.; KUMMER, David A.; MAHAROOF, Umar; NISHIMURA, Rachel; URBANSKI, Maud; VENKATESAN, Hariharan; WANG, Aihua; WOLIN, Ronald L.; WOODS, Craig R.; FOURIE, Anne; XUE, Xiaohua; CUMMINGS, Maxwell D.; JONES, William Moore; GOLDBERG, Steven; WO2015/57205; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 583-42-6,Some common heterocyclic compound, 583-42-6, name is 5-Fluoro-1H-benzo[d]imidazole-2(3H)-thione, molecular formula is C7H5FN2S, 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.

EXAMPLE I 9 Preparation of 5-fluoro-2-[[(4-cyclopropylmethoxy-2-pyridinyl)methyl)thio]-1H-benzimidazole To 5-fluoro-2-mercapto-1H-benzimidazole (0.88 g, 0.0051 mol) in methanol (25 ml) NaOH (0.2 g, 0.0051 mol) dissolved in H2 O (1 ml) and 4-cyclopropylmethoxy-2-chloromethylpyridine hydrochloride (0.91 g, 0.0046 mol) dissolved in methanol (10 ml) were added in the given order. The mixture was heated to boiling and NaOH (0.2 g, 0.005 mol) dissolved in H2 O (1 ml) was added and the mixture was refluxed for 1 hour. After evaporation of methanol, CH2 Cl2 (75 ml) and H2 O (50 ml) were added and pH adjusted to 10. The mixture was vigorously stirred, the phases were separated, the organic phase was dried over Na2 SO4 and evaporated giving the desired product (1.25 g, 72%). NMR data for the product is given below.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Fluoro-1H-benzo[d]imidazole-2(3H)-thione, its application will become more common.

Reference:
Patent; Aktiebolaget Hassle; US5049674; (1991); 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. 87233-54-3, name is 2-Chloro-1-(2-ethoxyethyl)-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., name: 2-Chloro-1-(2-ethoxyethyl)-1H-benzo[d]imidazole

c) Intermediate (23) (15.1 g), 2-chloro-1-(2-ethoxyethyl)-1H-benzimidazol (13.5 g) and copper (3.84 g) were stirred at 150 C. for 4 hours. The mixture was taken up in CH2 Cl2 and filtered. The filtrate was washed with a NH4 OH solution and with water. The organic layer was dried, filtered and the solvent evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2 Cl2 /CH3 OH 97/3). The pure fractions were collected and the solvent evaporated, yielding 20 g (77%) of (+-)-ethyl cis-4-[[1-(2-ethoxyethyl)-1H-benzimidazol-2-yl]amino]-2-(phenylmethyl)-1-piperidinecarboxylate (interm. 24).

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; Janssen Pharmaceutica N.V.; US6110939; (2000); A;,
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 4857-06-1 as follows. COA of Formula: C7H5ClN2

[0267] To a solution of 2-chloro-1H-benzo[d]imidazole (916 mg, 6 mmol) in 10 mL of dry DMF, which was cooled to 0 C., was careffilly added NaH (240 mg, 10.8 mmol) in small portions. The mixture was stirred for 15 minutes at this temperature. Then, methyl iodide (0.41 mL, 6.6 mmol) was added under continuous stirring for an additional 15 minutes. When thin layer chromatography (TLC) showed full conversion, the mixture was poured into 60 mL of water and a white solid precipitated. The precipitate was collected by filtration and dried in vacuo to obtain 2a 650 mg (65%) of pure product as a white solid. ?H NMR (400 MHz, DMSOd 5) oe 7.62-7.54 (m, 2H), 7.34-7.27 (m, 1H), 7.27-7.20 (m, 1H), 3.80 (s, 3H)

According to the analysis of related databases, 4857-06-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYLOR COLLEGE OF MEDICINE; O’Malley, Bert W.; Lonard, David Michael; Wang, Jin; Xu, Jianming; Chen, Jianwei; (47 pag.)US2017/290830; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 492-98-8, name is 1H,1’H-2,2′-Biimidazole, 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. name: 1H,1’H-2,2′-Biimidazole

A methanol solution (10 mL) of Cu(ClO4)2¡¤6H2O (0.33 g, 2 mmol) was initially reacted with acetylacetone (0.02 g, 2 mmol) treated with NaOH (0.040 g, 1.0 mmol) in water (10 mL) under magnetic stirring at room temperature. After 30 min, a 20 mL methanolic solution of the biimidazole (0.15 g, 2 mmol) was added to the solution and the resulting mixture was stirred for 2 h at room temperature. The green colored solid was isolated and washed with cold aqueous methanol and finally dried over P4O10 (Yield: 67%).

The synthetic route of 1H,1’H-2,2′-Biimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nagasubramanian, Soundarajan; Thamilarasan, Vijayan; Jayamani, Arumugam; Kang, Sung Kwon; Kim, Young-Inn; Sengottuvelan, Nallathambi; Bulletin of the Korean Chemical Society; vol. 34; 6; (2013); p. 1875 – 1878;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 26663-77-4, A common heterocyclic compound, 26663-77-4, name is Methyl benzimidazole-5-carboxylate, molecular formula is C9H8N2O2, 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.

3.50 g of methyl 1H-benzimidazole-5-carboxylate hydrochloride and 6.9 ML of triethylamine were suspended in 35 ML of methylene chloride, to which 5.05 g of trityl chloride was added in small portions at 5 to 10C, and this mixture was stirred for one hour at the same temperature.. The reaction mixture was added to a mixture of ethyl acetate and water, and then the organic phase was separated therefrom.. After the resultant organic phase was washed with water and a saturated sodium chloride solution successively, the washed phase was dried over anhydrous sodium sulfate, and the solvent was distilled out under reduced pressure.. The resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=3:1] to yield 3.55 g of a mixture of methyl 1-trityl-1H-benzimidazole-5-carboxylate and methyl 3-trityl-3H-benzimidazole-5-carboxylate as white foam. methyl 1-trityl-1H-benzimidazole-5-carboxylate NMR(400MHz,CDCl3) delta value: 3.90(3H,s), 6.49(1H,d,J=8.8Hz), 7.15-7.19(6H,m), 7.31-7.34(9H,m), 7.61(1H,d,J=8.4Hz), 7.97(1H,s), 8.49(1H,s) methyl 3-trityl-3H-benzimidazole-5-carboxylate NMR(400MHz,CDCl3) delta value: 3.75(3H,s), 7.15-7.19(7H,m), 7.31-7.34(9H,m), 7.77(1H,d,J=8.4Hz), 7.87(1H,d,J=8.4Hz), 8.02(1H,s)

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; TOYAMA CHEMICAL CO., LTD.; Hirono, Shuichi; Shiozawa, Shunichi; EP1445249; (2004); 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. 58089-25-1, name is 2-Mercapto-5-benzimidazolecarboxylic Acid, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H6N2O2S

EXAMPLE 1 2-[3-(4-Acetyl-3-hydroxy-2-propylphenoxy)propyl-thio]benzimidazole-5-carboxylic acid A mixture of 2-mercaptobenzimidazole-5-carboxylic acid (3.25 g), 3-(4-acetyl-3-hydroxy-2-propylphenoxy)propylbromide (2.00 g) and potassium hydroxide (1.27 g) in ethanol (30 ml) was refluxed for 4 hours. Then, the reacting mixture was poured into ice-water, made acidic with concentrated hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then evaporated. The resulting residue was purified by silica gel column chromatography, eluding with dichloromethane-ethyl acetate-methanol (10:2:1), and recrystallized from n-hexane-ethyl acetate to give the title compounds (3.00 g, 67.1%) as pale yellow crystals, mp 106-108 C. Analysis (%) for C22 H24 N2 O5 S: Calcd. (Found); C, 61.67 (61.76); H, 5.65 (5.89); N, 6.54 (6.26).

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; Kyorin Pharmaceutical Co., Ltd.; US4942245; (1990); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem