Author: Jessica.F

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., category: imidazoles-derivatives

Preparation of ( 1 -methyl- l H-benzimidazol- – l methanolThe title compound was synthesized by esterification of l//-benzimidazole-5-carboxylic acid using methanol in presence of cone, sulphuric acid followed by N-methylation using methyl iodide in presence of potassium carbonate and subsequent reduction of the ester group by lithium aluminium hydride; NMR (300 MHz, DMSO- 6) delta 3.84 (s, 3H), 4.59 (s, 2H), 5.23 (br s, l H), 7.26 (d, J = 8.4 Hz, 1H), 7.52-7.58 (m, 2H), 8.23-8.31 (m, 1 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; GLENMARK PHARMACEUTICALS S.A.; LINGAM, Prasada, Rao, V., S.; THOMAS, Abraham; KHAIRATKAR-JOSHI, Neelima; BAJPAI, Malini; GULLAPALLI, Srinivas; DAHALE, Dnyaneshwar, Harishchandra; MINDHE, Ajit, Shankar; RATHI, Vijay, Eknath; WO2011/138657; (2011); 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. 6160-65-2, name is 1,1′-Thiocarbonyldiimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of 1,1′-Thiocarbonyldiimidazole

A solution of the amine (2.1 g, 8.7 mmol) in anhydrous CH2CI2 (40 ml_) was added dropwise over 2-5 minutes to an ice-NaCI bath cooled solution of 1 , 1 ‘-thiocarbonyldiimidazole (95%, 3.1 g, 17.4 mmol, 2 eq.) in anhydrous CH2CI2 (120 ml_). After 15 minutes, the cooling bath was removed and the reaction mixture was stirred at room temperature for 1 .5 hours after which time analysis by TLC (5% MeOH in CH2CI2) indicated complete consumption of the starting aniline. The mixture was cooled once again in an ice bath and 7 M NH3 in MeOH (13 mL, 91 mmol, 10.5 eq.) was added dropwise over 2-5 minutes. The bath was removed and the mixture was stirred over night at room temperature. Silica gel (~5 g) was added and the mixture was concentrated to dryness under reduce pressure. Flash column chromatography (RediSepRf Si02 (120 g), 100% CH2CI2? 10% MeOH in CH2CI2) gave the thiourea as an amber oil that solidified to a tacky residue upon standing (2.5 g, 96%).

The synthetic route of 6160-65-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DUKE UNIVERSITY; LIEDTKE, Wolfgang; (189 pag.)WO2017/177200; (2017); 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. 144690-33-5, name is Ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2′-(1-trityl-1H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C45H44N6O3

Example 2; 36.0 g (50.3 mmol) ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-(4-[2-(trityltetrazol-5-yl)-phenyl]phenyl}-methyl imidazole-5-carboxylate (Va) and 3.0 g (75.4 mmol) of NaOH were suspended in 413 ml dimethylacetamide. The suspension was then stirred at room temperature for 20 h and after that 6.9 g (50.3 mmol) of K2CO3 were added. The mixture was cooled to 0C and solution of 15.4 g (70.4 mmol) 4-chloromethyl-5-methyl-2-oxo-1,3-dioxolene in 39 ml of dimethylacetamide were slowly added. The mixture was slowly heated to 50C and stirred at this temperature for 2 h. After esterification was completed, the mixture was cooled to 10 C and poured into a mixture of 625 ml of ethyl acetate and 625 ml of 10 % NaCl, and stirred at 25 C for 15 min. The phases were separated and organic phase was washed 2x with 500 ml of 10 % NaCl, dried over Na2SO4 and filtered. The filtrate was concentrated up to ½ (approximately 270 g) at reduced pressure. To the resulting solution, 80 ml of ethanol and 8.3 ml (100 mmol) of conc. HCl were added and stirred at 24-26C for 3h. To the cooled mixture 600 ml of water was added and pH of the suspension was estimated to 5 by addition of 5 M NaOH. The phases were stirred for 15 min and separated. Water phase was reextracted with 150 ml of ethyl acetate. Collected organic phases were dried over Na2SO4, filtered and concentrated under reduced pressure. 560 ml of ethyl acetate were added and the mixture was evaporated again. After that, 300 ml of ethyl acetate were added and the mixture was cooled to 20 C and stirred for 1h, filtered off and washed with 20 ml of fresh ethyl acetate. The yield of the product (I) was 21 g (75 %).

The synthetic route of 144690-33-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KRKA, tovarna zdravil, d.d., Novo mesto; EP1816131; (2007); 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. 2849-93-6, name is 1H-Benzimidazole-2-carboxylic acid, A new synthetic method of this compound is introduced below., Formula: C8H6N2O2

To a warm solution of [(eta6-p-cymene)RuCl2]2 (30 mg,0.05 mmol) in ethanol (2.5 mL) a warm solution of HL (16 mg,0.1 mmol) in ethanol (2.5 mL) and triethylamine (13.92 mL), wereadded. The mixture was stirred at room temperature for 4 h. Thebright-yellow product was filtered off, washed with ethanol (2 mL),diethyl ether and dried in vacuo. Yield: 30.2 mg, 70.2%. Anal. Calcdfor C18H19ClN2O2Ru, %: C, 50.06; H, 4.43; N, 6.49. Found, %: C, 50.04;H, 4.54; N, 6.52. IR (ATR, cm1): 3069(m), 3025(w), 2961(s),2906(m), 2756(m), 1642(vs), 1591(m), 1529(s), 1475(s), 1328(s),1229(m). 1H NMR (199.97 MHz, DMSO-d6, delta , ppm): 14.04 (s, 1H,NH), 8.11e8.02 (m, 1H, CHL), 7.64e7.56 (m, 1H, CHL), 7.55e7.42 (m,2H, CHL), 6.06 (d, 1H, JHeH 5.8 Hz, CHcymene), 5.97 (d, 1H,JHeH 5.9 Hz, CHcymene), 5.82 (t, 2H, JHeH 5.7 Hz, CHcymene), 2.69(m, 1H, JHeH 6.9 Hz, eCH(CH3)2), 2.17 (s, 3H, eCH3), 1.11 (dd, 6H,JHeH 7.0 and 9.4 Hz, eCH(CH3)2). 13C NMR (50.28 MHz, DMSO-d6,delta, ppm): 18.68 (eCH3), 22.06, 22.11 (eCH(CH3)2), 31.04(eCH(CH3)2), 77.63, 80.25, 80.34, 81.91 (CHcymene), 98.02 (CeCH3),101.04 (CeCH(CH3)2), 114.10, 118.32, 124.49, 125.69 (CHL), 133.97,140.20 (CeCHL), 145.88 (CeCOO), 164.15 (eCOO). ESI-MS (MeOH):m/z 397.049 [M-Cl]+, 353.059 [M-Cl-CO2]+.

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; Panti?, Darko N.; Arancrossed D Signelovi?, Sandra; Radulovi?, Sini?a; Roller, Alexander; Arion, Vladimir B.; Grguri?-?ipka, Sanja; Journal of Organometallic Chemistry; vol. 819; (2016); p. 61 – 68;,
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. 15965-54-5, name is 2-Chloro-5-methoxy-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., Quality Control of 2-Chloro-5-methoxy-1H-benzo[d]imidazole

EXAMPLE 100 0.55 Gram of 2-chloro-5-methoxybenzimidazole, 0.2 g of thiourea and 10 ml of ethanol were mixed together and refluxed for 2 hours. Then, 5 ml of an aqueous solution containing 0.5 g of 3-methyl-8-bromo-5,6,7,8-tetrahydroquinoline and 0.3 g of sodium hydroxide was added thereto, and the resulting mixture was refluxed for 5 hours. After the reaction was completed, ethanol was removed by evaporation, to the residue thus obtained was added water, then extracted with chloroform, the chloroform extract was dried with anhydrous magnesium sulfate, and chloroform was removed by evaporation. The residue thus obtained was purified by means of a silica gel column chromatography (eluent: dichloromethane/methanol=100/1) to yield 0.5 g of 8-(5-methoxy-2-benzimidazolyl)thio-3-methyl-5,6,7,8-tetrahydroquinoline in the form of colorless caramel-like substance. NMR (CDCl3) delta: 1.60-2.00 (m, 2H), 2.00-2.40 (m, 2H), 2.27 (s, 3H), 2.72 (t, 2H), 3.78 (s, 3H), 4.78 (t, 1H), 6.77 (dd, 1H), 7.00 (d, 1H), 7.22 (d, 1H), 7.40 (d, 1H), 8.23 (d, 1H).

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; Otsuka Pharmaceutical Co., Ltd.; US4738970; (1988); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 39070-14-9, A common heterocyclic compound, 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, molecular formula is C5H7N3O3, 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.

EXAMPLE 61: 1-Methyl-2-nitro-5-imidazolaldehyde To a solution of 0.15 g. of 1-methyl-2-nitro-5-hydroxymethylimidazole in 20 ml. of benzene, 0.33 g. of MnO2 is added and the reaction mixture is heated on the steambath for 2 hours. After filtration and evaporation to dryness under vacuum, the crude product is crystallized from ethyl acetate and 0.060 g. (40.5%) of 1-methyl-2-nitro-5-imidazolaldehyde is obtained.

The synthetic route of 39070-14-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Gruppo Lepetit S.p.A.; US3954789; (1976); 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. 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-(1H-Imidazol-1-yl)ethanol

The mixture containing 1.0 g (8.9 mmol) of 1-(2-hydroxyethyl)imidazole and 2.99 g (9.8 mmol) of 1-hexadecylbromide dissolved in 10 mL of acetonitrile was boiled with reflux condenser for 24 h. The precipitate formed during cooling was filtered, purified by recrystallization from ethyl acetate and dried under vacuum. Yield: 2.25 g (58%). Mp=52-54 C.IR-spectrum (KBr), cm-1: 3532, 3330, 3134, 3069, 2917, 2850, 1564,1472, 1379, 1165,1071, 873, 792, 720. 1H NMR spectrum, 400 MHz(CDCl3), delta, ppm, J/Hz: 0.88 t (3H, J=6.8), 1.25-1.33m (26 H), 1.91m(2 H), 3.98 t (2H, J=4.91), 4.26 t (2H, J=7.64), 4.53 t (2H, J=7.90),7.31 d (1 H), 7.63 d (1 H), 9.73 s (1 H). ESI MS, m/z: 337.6[M-Br]+.Calculated, %: C21H41N2OBr: C 60.42; H 9.89; N 6.71; Br 19.14; found,%: C 60.23; H 10.12; N 6.45; Br 19.07.

According to the analysis of related databases, 1615-14-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kuznetsova, Darya A.; Gabdrakhmanov, Dinar R.; Lukashenko, Svetlana S.; Voloshina, Alexandra D.; Sapunova, Anastasiia S.; Kashapov, Ruslan R.; Zakharova, Lucia Ya.; Chemistry and Physics of Lipids; vol. 223; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 3034-42-2, name is 1-Methyl-5-nitroimidazole, 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 3034-42-2, Recommanded Product: 3034-42-2

General procedure: To a solution of 1-methylimidazole derivatives (1 mmol) in adequate volume of acetonitrile, was added 1.5 mmol of 2-bromoacetophenone (1.8 mmol of ethylbromoactate). The reaction mixture was refluxed. When the reaction was(TLC), the solvent volume was reduced and the crude product was then filtered off and washed with cold acetonitrile.

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, 1-Methyl-5-nitroimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Bahnous, Mebarek; Bouraiou, Abdelmalek; Chelghoum, Meryem; Bouacida, Sofiane; Roisnel, Thierry; Smati, Farida; Bentchouala, Chafia; Gros, Philippe C.; Belfaitah, Ali; Bioorganic and Medicinal Chemistry Letters; vol. 23; 5; (2013); p. 1274 – 1278;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 15469-97-3, name is 1-Trityl-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 15469-97-3, Application In Synthesis of 1-Trityl-1H-imidazole

Take the imidazole salt (395 mg, 0.5 mmol), 1-trityl imidazole (550 mg, 1.8 mmol), anhydrous potassium carbonate (61 mg, 4.4 mmol), palladium dichloride (78.5 mg, 44 mmol) After vacuuming with nitrogen, anhydrous THF (6 mL) was added and the mixture was refluxed for 20 h. After the reaction solution was cooled to room temperature, it was diluted with dichloromethane, and the crude product was purified by column chromatography.The pale yellow product was obtained 278 mg, yield 53percent.

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

Reference:
Patent; Tianjin Normal University; Liu Guiyan; Han Fangwai; Liu Chengxin; Xu Ying; (9 pag.)CN108690086; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]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 152628-02-9, Formula: C19H20N4

l-Ethyl-2-[4′-(bromomethylphenyl)]benzoate (30.30 g, 85.5%) was dissolved in N1N- dimethylformamide (100 ml) at 2 + 20C and 4-methyl-6-(l -methyl- 1-benzimidazolyl)- 2-propyl-l-benzimidazole (25 g) at 2 +/- 20C was added to the above solution followed by sodium hydroxide (3.42 g). Thereafter, stirring was continued at 2 +/- 20C till the completion of the reaction. Methylene chloride (125 ml) was added to the above reaction mass followed by DM water (250 ml, 22 +/- 20C) at 2 +/- 20C. Stirring was continued at 22 +/- 20C for 15 min and the layers were separated and the aqueous layer was extracted with methylene chloride (25 ml) at 22 +/- 20C. The combined organic extract was washed with DM water (125 ml) at 22 +/- 20C and the organic layer was concentrated till the mass temperature reaches to 6O0C at atmospheric pressure. Ethanol (75 ml) was added to the concentrated mass (Contains Telmisartan ethyl ester) at 600C and the concentration was continued till the vapor temperature reaches to 820C. The concentrated mass was cooled to 45 + 5 and diluted with ethanol (100 ml) followed by aqueous sodium hydroxide (prepared by dissolving 10.87 g of sodium hydroxide in 25 ml of DM water) at 45 + 50C in 15 +/- 5 min was added and the contents were heated to reflux at 78 +/- I0C. Thereafter, stirring was continued at reflux temperature (78 +/- I0C) till completion of the reaction. The reaction mass was concentrated at atmospheric pressure till the mass temperature reaches to 80 +/- 20C and DM water (375 ml, 28 +/- 20C) was added to the residue followed by methylene chloride (50 ml) and stirred for 10 min at 22 + 20C. The layers were separated and methylene chloride (200 ml) was added to the aqueous layer at 22 + 20C and pH was adjusted to 4.1 +/- 0.1 with hydrochloric acid (-17 ml, 30%w/w) and stirring was continued for 10 min at 22 +/- 20C. The layers were separated and the organic layer was washed with DM water (50 ml) at 28 + 20C. The organic layer was diluted with LambdazetaN-dimethylformamide (125 ml) at 28 + 20C and seeded with Telmisaratn Form A. Thereafter, the solution was kept on standing at 28 +/- 20C for 30 min and Telmisartan Form A crystallizes out. The resulting slurry was concentrated at atmospheric pressure till the mass temperature reaches to 84 +/- 20C. The slurry was cooled to 2 +/- 20C and stirred for Ih at this temperature. The product was filtered and washed with pre-cooled N,iV-dimethylformamide (25 ml, 0 +/- 20C) followed by pre-cooled ethanol (50 ml, O0C) and dried to obtain Telmisartan (30 g ) was having more than 99.7 % of HPLC purity.

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, 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AUROBINDO PHARMA LIMITED; KORRAPATI, Venkata Vara Prasada Rao; INTI, Venkata Subramanyeswara Rao; ANANTA, Rani; MEENAKSHISUNDERAM, Sivakumaran; WO2010/4385; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem