Month: November 2020

1003-21-0, Adding a certain compound to certain chemical reactions, such as: 1003-21-0, name is 5-Bromo-1-methyl-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 1003-21-0.

5-Bromo-1-methyl-1H-imidazole (0.50mmol), Pd(PPh3)2Cl2 (0.025mmol, 5.0mol%), K2CO3 (1.0mmol, 2.0mol equivalent), DMF (2.0mL), distilled water (2.0mL) and the corresponding phenylboronic acid (0.60mmol), were added in a 10mL round bottom flask. The mixture was stirred at 90C for 24h. After completion of the reaction, the mixture was cooled down to room temperature and extracted 3 times with ethyl acetate. The combined ethyl acetate extract was dried using anhydrous MgSO4. The solvent was removed under reduced pressure and the product was purified by silica gel column chromatography using hexane-ethyl acetate (1:1) followed by 7% methanol in ethyl acetate as an eluent.2.2.1 13 5-(4-Methoxyphenyl)-1-methyl-1H-imidazole (1) (0007) Yellow solid; isolated yield (83%); 1H NMR (500MHz, CDCl3) delta (ppm): 7.48 (s, 1H, C-H- arom), 7.30 (d, 2H, J=8.8Hz, C-H arom), 7.03 (s, 1H, C-H-arom), 6.96 (d, 2H, J=8.5Hz, C-H arom), 3.84 (s, 3H, CH3), 3.62 (s, 3H, CH3). 13C NMR (125MHz, CDCl3) delta (ppm): 32.20, 55.20, 114.03, 122.06, 127.39, 129.54, 129.78, 133.07, 138.47, 159.28 (C- arom); IR (v, cm-1): 3084, 2947, 1899, 1720, 1611, 1552,1491, 1234, 1116, 1023; GC-MS m/z: 188 (M+1). Anal. Calc. for C11H12N2O (188): C, 70.19; H, 6.43; N, 14.88. Found: C, 70.35; H, 6.83; N, 14.80.

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-methyl-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Ibrahim, Mansur; Malik, Imran; Mansour, Waseem; Sharif, Muhammad; Fettouhi, Mohammed; El Ali, Bassam; Journal of Organometallic Chemistry; vol. 859; (2018); p. 44 – 51;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

35203-44-2, A common compound: 35203-44-2, name is 1-Propyl-1H-imidazole, belongs to imidazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Weigh 184g of 1,3-propane sultone, and add 1L of ethyl acetate to the reactor, and install a constant pressure dropping funnel.Magnetic stirrer and reflux condenser, slowly add 123g N-propyl imidazole when heated to 60 ¡ã C in a water bath.After the completion of the dropwise addition, the system was kept at 80 ¡ã C for 2 h to produce a white precipitate;The system was subjected to vacuum filtration, and the cake was washed with ethyl acetate.It is dried in an oven at 100 ¡ã C, and the obtained product is 1-(3-sulfonate)propyl-3-propylimidazolium salt;The 1-(3-sulfonate)propyl-3-propylimidazolium salt is dissolved in water, and concentrated sulfuric acid is added to carry out the reaction at 85 ¡ã C.The water is then removed to give a pale yellow viscous liquid product which is the 1-propyl-3-propanesulfonic acid imidazolium hydrogensulfate ionic liquid.

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-Propyl-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hangzhou Geng Lan Biological Technology Co., Ltd.; Dong Qiuyue; Yang Caihua; (6 pag.)CN109053372; (2018); 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 26576-46-5 as follows. 26576-46-5

Formation of the dispersion synergist SYN-D was accomplished by diazotation of compound 6 and subsequent coupling with compound 3. according to the following synthesis scheme: [Show Image] 17.3 g (0.1 mol) of compound 6 in 300 mL water was dissolved by adding 10 mL (0.1 mol) of a 29% sodiumhydroxide-solution. 8.97 g (0.13 mol) of sodiumnitrite was added and the colourless solution was dropwise added to cooled concentrated hydrochloric acid (29.98 mL; 0.36 mol). The diazonium-salt was kept at a temperature between 0 and 5 C. After 15 minutes the excess of nitrite was neutralized by adding 3.0 g (0.03 mol) of sulfamic acid and a pH of 7 was obtained by adding 25.2 g (0.3 mol) of sodiumcarbonate. While the diazionium-salt was made, 23.3 g (0.1 mol) of compound 3 was dissolved in a mixture of 500 mL methanol and 10.0 mL (0.1 mol) 29 % sodiumhydroxide-solution. This solution was dropped into the diazonium-salt solution and a yellow suspension is immediately formed. The temperature was maintained between 0 and 5 C for about 3 hours and the yellow product was filtered and washed with methanol. The yield was 98 %.

According to the analysis of related databases, 26576-46-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Agfa Graphics N.V.; EP1790697; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

22884-10-2, Adding a certain compound to certain chemical reactions, such as: 22884-10-2, name is 2-(1H-Imidazol-1-yl)acetic acid, 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 22884-10-2.

To a 50 mL flask was added 4-trifluoromethyl-2-azidoaniline1c (1 mmol), alpha-bromotrifluoroacetone (1.2mmol) And potassium carbonate (1.5mmol), React at 45 C, The reaction solvent was chloroform (20 mL). After 2 hours of reaction, Additional diphenylmethylphosphine (1.5 mmol) was added. The reaction was carried out at 30 C, and after continuing the reaction for 3 hours, The solvent chloroform was removed under reduced pressure. The intermediate was transferred to a solution of triphenylphosphine (2.5 mmol) and elemental iodine (2.5 mmol) in chloroform (15 mL). Then add imidazoleacetic acid (1.5 mmol), React at 45 C, Reaction for 2 hours, After the reaction is completed, The solvent chloroform was removed under reduced pressure. The primary product was subjected to column chromatography to give 0.192 g of the title compound 2c, yield 51%.

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, 2-(1H-Imidazol-1-yl)acetic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hubei Wenli College; He Ping; Wang Liping; Pei Fei; Jin Shan; Ren Zhilin; Wang Long; (10 pag.)CN109400589; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 139481-72-4, name is Trityl candesartan, molecular formula is C43H34N6O3, 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. 139481-72-4

Step I: Preparation of N-trityl candesartan cilexetilA mixture of N-trityl candesartan (Form A: 120 gm), potassium carbonate (48.58 gm), cilexetil chloride (54.48 gm) and dimethyl formamide (180 mL) at ambient temperature was heated to 60 C to 65 C followed by stirring at the same temperature for 2 hours and 30 minutes. The reaction mixture was cooled to 25 C to 30 C followed by addition of dichloromethane (600 mL) and ice cooled de-ionized water (1200 mL) at 10 C to 15 C to the reaction mass. The reaction was further stirred at 15 C to 20 C for 30 minutes followed by extraction of the aqueous layer with dichloromethane (120 mL) at 15 C to 30 C and washing with de-ionized water (2×600 mL) at ambient temperature.The organic layer was concentrated completely under vacuum at 30 C to 35 C followed by removal of traces of dichloromethane with cyclohexane (120 mL) and the further addition of cyclohexane (360 mL) to the residue at the ambient temperature. The reaction mixture was stirred at the same temperature for 14 hours followed by filtration and washing of the solid with cyclohexane (120 mL) which was suck dried under vacuum for 1 hour. Dichloromethane was again added (360 mL) at ambient temperature to the isolated solid followed by heating and stirring of the reaction mass at 30 C to 35 C for 30 minutes. The organic layer was concentrated under vacuum at 30 C to 35 C, cyclohexane (300 mL) added and the reaction mass was stirred further for 5 hours at the same temperature. The solid was filtered, washed with cyclohexane (120 mL) and suck dried under vacuum for 1 hour followed by further drying under vacuum for 16 hours at 35 C to 40 C.Chromatographic purity: 98.8%N-trityl desethylcandesartan cilexetil- 0.28%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 139481-72-4, its application will become more common.

Reference:
Patent; RANBAXY LABORATORIES LIMITED; SANJEEVI, Lakshmipathi V.; ALLADA, Suresh; KUMAR, Ashok; SINGH, Kaptan; GUNTU, Srinivasa Rao; WO2011/92666; (2011); 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. 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., 33543-78-1

To a stirred solution of hydroxylamine-o-sulfonic acid (26.64 g, 235.8 mmol, 3.0 eq) in H20 (17 mL) at 0 C, ethyl lH-imidazole-2-carboxylate (11.0 g, 78.6 mmol, 1.0 eq) was added and the resulting mixture was stirred at 90 C for 30 min. The mixture was cooled to RT and K2CO3 (3.6 g, 26.2 mmol, 1.0 eq) was added in portions. The resulting mixture was stirred at RT overnight, filtered and rinsed with H20 (10 mL x 3). The filtrate was extracted with ethyl acetate (50 mL x 5). The combined organic layer was washed with brine, dried over Na2S04 and filtered. The filtrate was evaporated in vacuo and the residue was purified by flash column chromatography on silica gel (1% MeOH in DCM) to afford ethyl 1 -amino- lH-imidazole-2-carboxylate (800 mg, 6.5 % yield). ESI-MS m/z: 156.1 [M+H]+.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; INFINITY PHARMACEUTICALS INC.; INTELLIKINE, LLC; CASTRO, Alfredo, C.; EVANS, Catherine, A.; JANARDANANNAIR, Somarajannair; LESCARBEAU, Andre; LIU, Tao; SNYDER, Daniel, A.; TREMBLAY, Martin, R.; REN, Pingda; LIU, Yi; LI, Liansheng; CHAN, Katrina; WO2013/12915; (2013); 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. 583-39-1, name is 2-Mercaptobenzimidazole, A new synthetic method of this compound is introduced below., 583-39-1

General procedure: To an orange suspension of [Pd2(kappa2:C, N-mazb)2(mu-Cl)2] (0.025g, 0.040mmol) in dichloromethane (5mL), N-methylimidazolidine-2-thione (0.012g, 0.080mmol) was added in presence of Et3N base (0.5mL). The color of the reaction mixture became red brown and was stirred for 5-6h. The solution was filtered and methanol (5mL) was added and was left to evaporate slowly. The red brown crystals of compound 7 were obtained after a period of 4-5d.

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; Sandhu, Amanpreet K.; Lobana, Tarlok S.; Sran, Balkaran S.; Hundal, Geeta; Jasinski, Jerry P.; Journal of Organometallic Chemistry; vol. 861; (2018); p. 112 – 124;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

288-32-4, Adding a certain compound to certain chemical reactions, such as: 288-32-4, name is 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 288-32-4.

General procedure: N-Butylimidazole and N-octylimidazole were synthesized fol-lowing the procedure of literature [44]: To a round-bottomedflask, imidazole (6.0 g, 88 mmol), 1-bromobutane/1-bromooctane(90 mmol), acetonitrile (50 mL) and potassium hydroxide (9.9 g,177 mmol), were added in sequence. The reaction mixture wasrefluxed for 4 h and then cooled down to room temperature. Afterevaporating the solvent, the residue was purified by a flash col-umn chromatography utilizing ethyl acetate/methanol (v/v = 25:1)as eluent. The pure product of 1-butylimidazole/1-octylimidazolewas isolated as a pale yellow oil (?83%). N-Octylimidazole:1H NMR: (CDCl3): (ppm) = 0.87 (t, J = 6.5 Hz,3H, CH3), 1.28 (br, 10H, CH2), 1.77 (br, 2H, CH2), 3.92 (t, J = 7.2 Hz,2H, CH2), 6.90 (s, 1H, ImH), 7.04 (s, 1H, ImH), 7.45 (s, 1H, ImH).13CNMR (CDCl3): (ppm) = 13.9, 22.5, 26.4, 28.9, 29.0, 31.0, 31.6, 46.9,118.7, 129.2, 136.9.

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; Duan, Shuhui; Jing, Xinyao; Li, Dandan; Jing, Huanwang; Journal of Molecular Catalysis A: Chemical; vol. 411; (2016); p. 34 – 39;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

144689-93-0, A common heterocyclic compound, 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, molecular formula is C12H20N2O3, 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.

Synthesis of 1 was achieved by literature known method [1, 2]. To a solution of 1 (5 g, 20.82 mmol) in ethanol (50 mL), hydrazine hydrate (3.03 mL, 62.46 mmol) was added. The reaction mixture was refluxed for 16 h for completion of the reaction which was monitored by TLC. Solvent was removed under reduced pressure and cooled by adding ice cold water. The resulting precipitate was filtered, washed with cold water and recrystallized from ethanol to get the desired compound 2.

The synthetic route of 144689-93-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kumara; Suhas; Suyoga Vardhan; Shobha; Channe Gowda; Bioorganic Chemistry; vol. 86; (2019); p. 34 – 38;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A common compound: 7189-69-7, name is 1,1′-Sulfonyldiimidazole, belongs to imidazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 7189-69-7

Methyl 5-(phenethylthio)-2-(l-phenylpiperazine-4-sulfonamido)benzoate (3q) Synthesized using reported procedure with modification (see, e.g., Beaudoin, S.; Kinsey, K. E.; Burns, J. F. J. Org. Chem. 2003, 68, 115-119). To a round-bottom-flask under nitrogen 1- (lH-imidazol-l-ylsulfonyl)-lH-imidazole 14 (80 mg, 0.4 mmol, 2 equiv.) and dry CH2CI2 (10 mL) were added at 0 C. MeOTf (72 mg, 0.05 mL, 0.44 mmol, 2.2 equiv.) was added and then the mixture was stirred for 3 hours. The solvent was removed under reduced pressure and re dissolved in dry CH3CN (10 mL) at room temperature. 1 -Phenylpiperazine (65 mg, 0.061 mL, 0.4 mmol, 2 equiv.) was added and then the mixture was stirred for 16 hours. The reaction mixture was concentrated under reduced pressure. The crude product was dissolved in dry CH2C12 (10 mL) at 0 C. MeOTf (72 mg, 0.05 mL, 0.44 mmol, 2.2 equiv.) was added, followed by stirring the mixture for 2 hours. The solvent was removed under reduced pressure and re dissolved in dry CH3CN (10 mL) at room temperature. Methyl 2-amino-5- (phenethylthio)benzoate 2 (57.5 mg, 0.2 mmol, 1.0 equiv.) was added and then the mixture was heated to reflux for 16 hours. The reaction mixture was then allowed to cool down and concentrated under reduced pressure. The crude product was purified by flash column chromatography (ethyl acetate_hexanes=30:70) on silica gel to afford 3q (75 mg, 73% over 2 steps) as yellow oil which solidified upon standing. lH NMR (300 MHz, CDC13) delta 10.45 (s, 1H), 8.02 (d, J= 2.1 Hz, 1H), 7.68 (d, J= 9.0 Hz, 1H), 7.51 (dd, J = 9.0, 3.0 Hz, 1H), 7.31-7.16 (m, 7H), 6.92-6.86 (m, 3H), 3.94 (s, 3H), 3.44- 3.41 (m, 4H), 3.19-3.11 (m, 6H), 2.92-2.87 (m, 2H); 1 C NMR (75 MHz, CDC13) delta 167.98, 150.59, 139.81, 139.76, 136.43, 132.74, 129.78, 129.22, 128.52, 128.48, 126.53, 120.80, 119.24, 116.79, 115.36, 52.67, 49.07, 46.28, 36.07, 35.64.

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, 7189-69-7, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; NIKOLOVSKA-COLESKA, Zaneta; STUCKEY, Jeanne A.; MADY, Ahmed; MIAO, Lei; (140 pag.)WO2016/172218; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem