Month: November 2020

288-32-4, 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. 288-32-4, name is 1H-Imidazole, A new synthetic method of this compound is introduced below.

Example 1. Preparation of (1-f4- (4-chlorophenvl)-2-hydroxy-n-butvll-imidazole) (IV); To a solution of 56.7 g (0.26 mol) of 1-chloro-4-chlorophenyl-2-butanol (J. of Medicinal Chemistry, 1978. Vol. 21. No. 8. p. 842) in 200 ml of toluene 36.2 g (0.9 mol) of sodium hydroxide dissolved in 100 ml of water, 6.4 g (0.028 mol) of benzyltriethyammonium chloride and 35.2 g (0.51 mol) of imidazole (III) are added. The reaction mixture is heated at 93-95 C for one hour then the temperature is returned to about 60 C, the phases are separated and to the organic layer water (100 ml) is added. The mixture is first stirred at 22-25 C for 1 hour then at 0-5 C for two hours. The crystals are separated by filtration, washed with water (2 x 35 ml) of 0-5 C to yield 74 g of wet (1- [4- (4-chlorophenyl)-2-hydroxy-n-butyl]-imidazole) which is dried at maximum 50 C in vacuo to give 61.6 g (95 %) of the product. Recrystallization from ethyl acetate gives 52.4 g (85 %) of dry product melting at 104-106 C.

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; RICHTER GEDEON VEGYESZETI GYAR RT.; WO2005/70897; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1632-83-3, 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. 1632-83-3 name is 1-Methylbenzimidazole, 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.

General procedure: 4.3 General procedure for CuO-catalyzed arylation and alkenylation of 1,3-azole (0012) Under argon, 0.5mmol of the bromobenzene or bromoalkene was added to the reaction mixture containing 0.25mmol of the benzoxazole, 0.5mmol K2CO3, 0.025mmol CuO, and 0.075mmol PPh3, followed by the addition of 2mL dry diglyme. The sealed reaction tube was stirred at 160C for 5-24h. After cooling, the reaction mixture was centrifuged to remove solid and separated the organic phase. Then, organic phase was extracted and dried over anhydrous MgSO4, and concentrated under reduced pressure after filtered. The residue was purified by column chromatography on silica gel eluted to afford corresponding product.

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

Reference:
Article; Zhang, Wu; Tian, Yujie; Zhao, Na; Wang, Yuanyuan; Li, Jia; Wang, Zhenghua; Tetrahedron; vol. 70; 36; (2014); p. 6120 – 6126;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

288-32-4, 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. 288-32-4, name is 1H-Imidazole, A new synthetic method of this compound is introduced below.

Preparation of Imidazol-1-ylacetic acid. Into a 1-L, three-necked RB flask is charged 100g of imidazole, 40ml of DMF, 400ml of toluene, 180g of potassium carbonate and lOg of potassium iodide. After stirring for 10min, 240g of methyl chloroacetate was added slowly over a period of 1.5-2. Ohr at 25- 30C. The reaction mass was kept under stirring at 25-30 C for lhr and slowly heated to 60-65C. After maintaining at the same temperature for 2-3h reaction was found to be over by TLC. The reaction mass was cooled to 25-30C and added 200ml of ethyl acetate. The reaction mass was stirred for 20-30min and decanted the top organic layer. The residue was once again extracted with ethyl acetate (200ml). Finally water (200ml) was added to the reaction mass and stirred for 30min. Inorganic salts were removed by filtration and the filtrate extracted with ethyl acetate (2 x 200ml). All ethyl acetate extractions were combined and distilled off under vaccum to get 220g of crude mass. The crude mass was suspended in 500ml of water and refluxed for 4-5h. Reaction mass became a clear liquid. The reaction mass was treated with charcoal and distilled off water under vaccum keeping the temperature below 80C. The residue was cooled to 25-30C and added 250ml of methanol. The suspension was stirred for lh and filtered the mass. The wet cake was washed with 50ml of methanol and dried at 50-60C to get 150g of white crystalline solid of imidazol-1-ylacetic acid. Melting point is 268-269 C. Purity by HPLC is 99.2%.

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; NATCO PHARMA LIMITED; PULLA REDDY, Muddasani; USHA RANI, Vattikuti; VENKAIAH CHOWDARY, Nannapaneni; WO2005/63717; (2005); 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. 26576-46-5, name is 5-Acetoacetlamino benzimdazolone, This compound has unique chemical properties. The synthetic route is as follows., 26576-46-5

Dispersion synergist SYN-20; Formation of the dispersion synergist SYN-20 was accomplished by diazotation of compound 14 and subsequent coupling with compound 3. according to the following synthesis scheme: [Show Image] 21.72 g (0.1 mol) of compound 14 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 88 %.

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; Agfa Graphics N.V.; EP1790697; (2007); 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. 33468-69-8, name is 4-(Trifluoromethyl)-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., 33468-69-8

l-(4-Ethynyl-2-methoxyphenyl)-4-(trifluoromethyl)-lH-imidazole. 4-Fluoro-3-methoxybenzaldehyde (2.57 g, 16.7 mmol), 4-trifluoromethylimidazole (4.54 g, 33.4 mmol), and K2CO3 (3.46 g, 25 mmol) were dissolved in 15 ml of DMF and stirred at 100 0C overnight. Cooled to room temperature and DMF removed in vacuo. The concentrated mass was taken up in EtOAc and water. Layers were separated and the aqueous layer was extracted twice with EtOAc. The organic extracts were combined, dried (Na2SO4), and concentrated. Chromatography on SiO2 (0-50% EtOAc/CH2Cl2) gave a cream-colored solid (1.67 g, 6.2 mmol, 37%). A solution of aldehyde intermediate (445 mg, 2.32 mmol) in 20 ml of MeOH was treated with K2CO3 (534 mg, 3.86 mmol) and a solution of dimethyl (l-diazo-2-oxopropyl)phosphonate (522 mg, 1.93 mmol) in 5 ml of MeOH and stirred at room temperature overnight. MeOH was removed in vacuo and the concentrated mass was dissolved in EtOAc and washed sequentially with water, sat’d NaHCO3, and water. The organic layer was dried (Na2SO4) and concentrated to a yellow solid (493.2 mg, 1.9 mmol, 96%). 1H NMR (600 MHz, CDCl3) delta 7.77 (s, 1 H), 7.51 (t, J- 1.2 Hz, 1 H), 7.22 (d, J= 7.9 Hz, 1 H), 7.18 (dd, J= 7.9, 1.4 Hz, 1 H), 7.16 (d, J= 1.5 Hz, 1 H), 3.86 (s, 3 H), 3.16 (s, 1 H); MS (EI) [M+l]+ calc’d 267.1, found 267.2.

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; MERCK & CO., INC.; WO2008/156580; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1467-16-9, 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. 1467-16-9, name is 1H-Imidazole hydrochloride, This compound has unique chemical properties. The synthetic route is as follows.

TFA (991 muIota, 13.0 mmol) was added to a solution of 3-amino-7-cyano-5-{[2- (trimethylsilyl)ethoxy]methyl}-5/-/-pyrrolo[2,3- 5]pyrazine-2-carboxylate, Intermediate 166 (150 mg, 0.43 mmol) in CH2CI2 (2 ml). The resultant mixture was stirred at RT for 4.5 h. The reaction mixture was concentrated in vacuo, azeotroped with toluene (2 x 5 ml), then dried in vacuo to afford a red/orange solid (1 14 mg). A portion (83 mg) of the solid thus obtained was dissolved in MeOH (3 ml). Aqueous NaOH solution (5.0 M, 0.67 ml, 3.4 mmol) was added then the resulting mixture was heated at 60 C for 1 h then at 80 C for 1.5 h. The reaction mixture was allowed to cool to RT then filtered. The collected solid was washed with water then dried in vacuo to afford a brown solid (60 mg). The solid thus obtained was dissolved in DMF (1 ml) then CDI (78 mg, 0.48 mmol) and imidazole hydrochloride (25 mg, 0.24 mmol) were added. The reaction was stirred at RT for 10 min. Water (3 ml) was added then the reaction was stirred at RT for 5 min. The solid was collected by filtration, washed with water, then dried in vacuo to afford a brown solid (39 mg). The solid thus obtained was dissolved in DMF (1 ml) then 2-(aminomethyl)-1 ,3- diethyl-6-methoxy-1 /-/-1 ,3-benzodiazol-3-ium iodide, Intermediate 36 (45 mg, 0.13 mmol) was added. The resultant mixture was stirred at RT for 2.5 h then concentrated in vacuo. The crude material was purified by flash column chromatography on C18 (12 g). The column was eluted with MeCNihbO + 0.1 % TFA using the following gradient (% MeCN, column volumes): 2%, 2 CV; 2-37%, 18 CV; 37-48%, 1 CV; 48-89%, 3 CV; 89-100%, 1 CV; 100% 2 CV. The desired fractions were combined and lyophilised. The material thus obtained was further purified by preparative HPLC (Method A). The desired fractions were combined and lyophilised to afford the product as a yellow solid (3.5 mg, 1.7%). 1 H NMR (500 MHz, DMSO-cfe) delta 9.41 (t, J = 5.0 Hz, 1 H), 8.34 (s, 1 H), 8.23 (s, 1 H), 7.89 (d, J = 9.1 Hz, 1 H), 7.51 (d, J = 2.3 Hz, 1 H), 7.21 (dd, J = 9.1 , 2.3 Hz, 1 H), 7.09 (s, 2H), 5.01 (d, J = 5.4 Hz, 2H), 4.66 – 4.56 (m, 4H), 3.84 (s, 3H), 1.38 – 1.28 (m, 6H). LC/MS (System C): m/z (ESI+) = 419 [M+], Rt = 1.85 min, UV purity = 99%.

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; ENTERPRISE THERAPEUTICS LIMITED; MCCARTHY, Clive; HARGRAVE, Jonathan, David; HAY, Duncan, Alexander; SCHOFIELD, Thomas, Beauregard; WENT, Naomi; (261 pag.)WO2018/96325; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

The chemical industry reduces the impact on the environment during synthesis 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, I believe this compound will play a more active role in future production and life. 1003-21-0

Pd(PPh3)4 (55.9 mg, 48.4 mumol) was added to a mixture of 6 (300 mg, 0.484 mmol) and 5-bromo-1-methylimidazole (312 mg, 1.94 mmol) in aqueous Na2CO3 (2 M, 1.0 mL, 2.0 mmol) and anhydrous THF (9.0 mL), and the solution was stirred at room temperature for 15 min. The resulting two-phase system was refluxed under stirring overnight, and was then allowed to cool to room temperature. To this was added water (25 mL), and the mixture was extracted with CHCl3 (50 mL¡Á3). The organic layer was washed with water (25 mL), dried over anhydrous MgSO4, and filtered. After the solvent was removed by evaporation, the residue was subjected to SEC fractionation to obtain 1 (150 mg, 59%) as a bluish white solid. Mp: 188.7-189.1 C. IR (KBr, cm-1): 1339, 1276, 1185, 1110, 1055, 989. 1H NMR (500 MHz, CDCl3): delta 7.51 (s, br, 2H, ArH), 7.15 (d, J=1.1Hz, 2H, ArH), 7.00 (s, 2H, ArH), 3.68 (s, 6H, NCH3), 2.02 (s, 6H, CH3). 13C NMR (125 MHz, CDCl3): delta 142.1, 139.8, 129.7, 129.3, 125.7, 125.6, 125.4, 32.7, 14.4. MS (ESI+): m/z=529 [M+H]+. Anal. Calcd for C23H18F6N4S2: C, 52.27; H, 3.43; N, 10.60. Found: C, 52.03; H, 3.46; N, 10.54.

The chemical industry reduces the impact on the environment during synthesis 1003-21-0. I believe this compound will play a more active role in future production and life.

Reference:
Article; Iida, Hiroki; Umebayashi, Naofumi; Yashima, Eiji; Tetrahedron; vol. 69; 52; (2013); p. 11064 – 11069;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

3314-30-5, A common heterocyclic compound, 3314-30-5, name is 1H-Benzo[d]imidazole-2-carbaldehyde, molecular formula is C8H6N2O, 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.

Typical procedure for the preparation of Benzimidazolyl-benzimidazole; A solution of benzimidazole-2-aldehyde 1 (0.5 mmol) and diamine 2 (0.5 mmol) in dimethylacetamide (4mL) was stirred at 100 0C for 12h. Solvent was evaporated and residue was purified by preparative HPLC to give benzimidazole derivative 3. 1H NMR (300 MHz, MeOH-doe : S 2.52 (s, 3H), 2.85 (brs, 4H)5 3.25 (brs, 4H)5 7.05-7.15 (m, 2 H), 7.25-7.35 (s overlapped with m, 2 H)5 7.60-7.75 (m, 4H); LCMS mlz 333 (M + H+), ELSD 99percent.

The synthetic route of 3314-30-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHEMBRIDGE RESEARCH LABORATORIES, INC.; WO2007/56155; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

872-82-2, 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. 872-82-2 name is 2-(1H-Imidazol-5-yl)ethanol, 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.

4-lmidazoleacetic acid hydrochloride (5.93 g, 36.47 mmol) in methanol (125 mL) was saturated with HCI gas and stirred at room temperature for 5.5 h, then concentrated to give a quantitative yield of 4-imidazoleacetic acid methyl ester hydrochloride as a white solid which had NMR (MeOH- d4) delta 8.87 (d, J = 1.2 Hz, 1H), 7.46 (s, 1 H), 3.89 (s, 2H) 3.72 Patent; PFIZER PRODUCTS INC.; WO2007/34277; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

The chemical industry reduces the impact on the environment during synthesis 26576-46-5, name is 5-Acetoacetlamino benzimdazolone, I believe this compound will play a more active role in future production and life. 26576-46-5

To 30 parts of dimethylacetamide were added 5.6 parts of 3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid,And 2.6 parts of thionyl chloride were added, and the mixture was stirred at 40 to 50 C. for 0.5 hour. 3 parts of 4′-aminoacetanilide was added, and the mixture was heated at 90 to 100 C. for 3 hours. 30 parts of water and 8.3 parts of concentrated hydrochloric acid were added, and the mixture was stirred at 90 to 100 C. for 1 hour.It was cooled to 0 to 10 C., and 1.4 parts of sodium nitrite was added to diazotize. 5 parts of sodium hydroxide and 4.7 parts of 5- (acetoacetamido) -2-benzimidazolinone were dissolved in 150 parts of water, the aforementioned diazo solution was added, and the mixture was stirred at 20 to 30 C. for 4 hours, then 70 to 80 0> C for 1 hour. After filtration, washing with water and drying, 11.6 parts of a yellow pigment additive (H) represented by the following formula (H) was obtained.

The chemical industry reduces the impact on the environment during synthesis 26576-46-5. I believe this compound will play a more active role in future production and life.

Reference:
Patent; DAINICHISEIKA COLOR & CHEMICALS MANUFACTURING COMPANY LIMITED; YANAGIMOTO, HIROMITSU; (36 pag.)JP2017/125083; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem