Tag: M.W=200-300

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. 3543-72-4, name is Ethyl 4-(1-methyl-5-nitro-1H-benzo[d]imidazol-2-yl)butanoate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. 3543-72-4

[0075] 163 g (559.5 mmol) of compound (5) were dissolved in 1875 g ethanol. 14 g of palladium catalyst on activatedcarbon doped with iron (5% Pd, 1% Fe) and an additional 0.8 g of iron(II) sulfate 7-hydrate or 0.8 g of iron(III) nitrate 9-hydrate were added. Compound (5) was then hydrogenated at a hydrogen pressure of up to 4 bar until completeconversion of the starting compound (5).[0076] The catalyst was removed by filtration, and the ethanolic solution concentrated until a dry product remained.This residue was crystallized from propan-2-ol or ethyl acetate.[0077] The yield of compound (6) was 128 g (489,8 mmol) with a content of > 99 % (87.5 % of theory).[0078] The overall yield of compound (6) was 80.4% of theory in relation to 2-fluoro-5-nitroaniline. In comparison, thesynthesis according to DD34727 starting from N-1-methyl-4-nitrobenzene-1,2-diamine (CAS 41939-61-1) is characterizedby a yield of 39.0%.

The synthetic route of 3543-72-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HEYL Chemisch-Pharmazeutische Fabrik GmbH und Co. KG; Frey, Michael; Walther, Dirk-Detlef; EP2690096; (2014); 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

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

641571-11-1, 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. 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

1006361 A solution of 3 -((4-(5-methoxypyridin-3 -yl)pyrimidin-2-yl)amino)-4-methylbenzoic acid (6.4 g, 19.02 mmol) in NMP (64 mL) was dropwise charged with thionylchloride (2.7 g, 22.8 mmol) at room temperature and heated to 60 C for 1 h. The solution wascharged with 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline (5.5 g, 22.8 mmol) andheated to 90 C for 3 h. The reaction mixture was diluted with water (120 mL), adjusted pH to10 with 40% aqueous sodium hydroxide solution and stirred at 80 C for 30 mm. The reactionmixture was cooled to 40 C and the solid precipitated out was filtered and washed with water.The residue obtained was again stirred in water at 40 C for 1 h and solid was filtered and driedto give 5.60 g, 52% yield of the title compound as a white solid. ?H NMR (400 MHz, DMSO-= 10.61 (s, 1 H), 9.16 (s, 1 H), 8.88 (d, J= 1.34 Hz, 1 H), 8.56 (d, J= 4.91 Hz, 1 H), 8.36- 8.42 (m, 2 H), 8.28 (s, 1 H), 8.15 -8.21 (m, 2 H), 7.95 -8.00 (m, 1 H), 7.69-7.79 (m, 2 H),7.52 (d, J= 5.35 Hz, 1 H), 7.41 -7.50 (m, 2 H), 3.83 (s, 3 H), 2.37 (s, 3 H), 2.18 (s, 3 H); MS(ES): m/z = 560.30 [M+H] LCMS: tR = 2.61 mm.

The synthetic route of 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; COFERON, INC.; FOREMAN, Kenneth, W.; JIN, Meizhong; WANNER, Jutta; WERNER, Douglas, S.; WO2015/106292; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

71759-88-1, The chemical industry reduces the impact on the environment during synthesis 71759-88-1, name is 5-Iodo-1-methyl-1H-imidazole, I believe this compound will play a more active role in future production and life.

EXAMPLE 93B (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (4-cyanophenyl)(hydroxy)(1-methyl-1H-imidazol-5-yl)acetate A mixture of zinc dust (9.4 g, 143.7 mmol) in THF (5 mL) was treated with 1,2-dibromoethane (0.62 mL, 7.2 mmol), heated to 50 C., stirred for 15 minutes, and cooled to 30 C. The mixture was treated with chlorotrimethylsilane (0.91 mL, 7.2 mmol), stirred for 5 minutes, heated to reflux, treated slowly with 5-iodo-1-methyl-1H-imidazole (20.0 g, 96.2 mmol), and continued to reflux for 30 minutes. The reaction was cooled to room temperature and stirring was aborted to allow the excess zinc to settle to the bottom of the flask. A solution of magnesium bromide diethyl etherate (10.3 g, 39.9 mmol) and Example 93A (50.0 g, 79.8 mmol) in THF (100 mL) was cooled to -10 C. and treated with a solution of the 1-methyl-5-zinciodo-1H-imidazole from above in THF (120 mL) over 15 minutes. The mixture was warmed to room temperature, stirred for 18 hours, quenched with saturated NH4Cl (100 mL), and the layers were separated. The aqueous phase was extracted with ethyl acetate (300 mL) and the combined organic phases were washed with brine. The reaction mixture was filtered through diatomaceous earth (Celite), treated with toluene (250 mL), concentrated at a bath temperture of 60 C. The mixture was allowed to sit for 18 hours and then filtered. The filter cake was washed with toluene and dried under vacuum at 50 C. to provide 30.0 g (81% potent, 77% yield, 97.4% de). MS (ACPI) m/e 396 (M+H)+; 1H NMR (CD3OD) delta 8.02 (br s, 1H), 7.78 (d, 2H), 7.63 (d, 2H), 7.13 (br s, 1H), 4.76 (ddd, 1H), 3.49 (s, 3H), 2.06 (br d, 1H), 1.72-1.60 (m, 2H), 1.55-1.42 (m, 1H), 1.30 (m, 11), 1.14 (q, 1H), 1.07-0.98 (m, 2H), 0.95 (d, 3H), 0.94-0.84 (m, 1H), 0.66 (d, 3H), 0.50 (d, 3H).

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

Reference:
Patent; Claiborne, Akiyo K.; Gwaltney, II, Stephen L.; Hasvold, Lisa A.; Li, Qun; Li, Tongmei; Lin, Nan-Horng; Mantei, Robert A.; Rockway, Todd W.; Sham, Hing L.; Sullivan, Gerard M.; Tong, Yunsong; Wang, Gary; Wang, Le; Wang, Xilu; Wang, Wei-Bo; US2002/115640; (2002); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

67085-11-4, These common heterocyclic compound, 67085-11-4, name is 4-(4-Chlorophenyl)-1-(1H-imidazol-1-yl)butan-2-ol, 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.

Take 5kg of 1-(2-hydroxy-4-(4-chlorophenyl)butyl)-1H-imidazole and dissolve it sufficiently in 35kg of methylene chloride. 5kg of thionyl chloride was added dropwise at a rate of 1.5ml/s at 20C, and the temperature was slowly raised to 32C and the reaction was incubated for 1 hour. Then reflux at 60 C for 1 hour, slowly cooled to 15 C to obtain the reaction solution; In the reaction solution, 10 C. water was added at a rate of 0.5 ml/s with stirring, and the volume ratio of the reaction solution to water was 0.005:1. Anhydrous sodium carbonate was further added at 1.0 to 1.5 kg/L. After suction filtration, the solid was discarded, the liquid was concentrated at 55 C. until no dichloromethane was distilled off, and dried to obtain 1-(2-chloro-4-(4-chlorophenyl)butyl)-1-hydro-imidazole. The purity is 99.17%. The 1-(2-chloro-4-(4-chlorophenyl)butyl)-1H-imidazole was used as a raw material in Examples 1 to 5.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 67085-11-4.

Reference:
Patent; Zhuzhou Qianjin Pharmaceutical Co., Ltd.; Peng Kaifeng; Wen Fengqiu; Bai Lu; Li Sanxin; Gong Yun; Li Fujun; (12 pag.)CN105198816; (2018); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

26576-46-5, These common heterocyclic compound, 26576-46-5, name is 5-Acetoacetlamino benzimdazolone, 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.

244kg 1,2-bis(o-aminophenoxy)ethane, 600kg mass percentage concentration of 30% hydrochloric acid and 1500kg water was stirred and beaten. Add 2000kg ice to cool to 5 deg.C. Add 363kg mass percentage concentration of 40% sodium nitrite to start diazotization. At diazotization end, eliminate excess sodium nitrite, to give a diazonium salt solution.280kg 5-aminoacetylacetylbenzimidazolone, dissolved in 250kg mass percentage concentration of 30% aqueous sodium hydroxide and 3000kg of water. Adjust the temperature to 5 deg.C. Add in a fine stream 1500 mass concentration of 10% diluted acetic acid until the acid precipitation end, pH value of 7, to obtain a coupling solution.The diazonium salt solution was slowly added over 3 hours to the coupling solution to undergo reaction. The pH during the coupling process was maintained using 850kg 30% concentration sodium bicarbonate to control the system pH to 7. The coupling ends. Temperature was raised to 90 deg. C, and maintained at this temperature for 2 hours, filtered to give the crude pigment filter cake. 1660kg solid content of 40% of the crude pigment filter cake was added to 4000kgDMF slurried in good stirring and heated to reflux, 5-8 hours of incubation, washing, drying at 85-90 deg.C under pulverized to obtain 665kg products.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 26576-46-5.

Reference:
Patent; Shangyu?City Xinli Chemical Co.,Ltd.; Chen, Jianxin; Ni, Yuebiao; Zhang, Lixin; Fang, Biao; (15 pag.)CN105670340; (2016); 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

Dispersion synergist SYN-8; Formation of the dispersion synergist SYN-8 was accomplished by diazotation of compound 11 and subsequent coupling with compound 3 [Show Image] 18.1 g (0.1 mol) of compound 11 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 70 %.

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

124750-59-0, Name is 2-Propyl-1H-imidazole-4,5-dicarboxylic acid dimethyl ester, 124750-59-0, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

Part B: Preparation of 1-[(2′-Carbomethoxybiphenyl-4-yl)methyl]-4,5-dicarbomethoxy-2-n-propylimidazole 2-n-Propyl-4,5-dicarbomethoxyimidazole (2.00 g, 8.8 mmol, 1 eq.) was alkylated with 4′-bromomethyl-2-carbomethoxybiphenyl (2.70 g, 8.8 mmol, 1 eq.) by the procedure described in Example 1, Part A. Obtained 3.87 g of a yellow oil which was suitable for further transformation. NMR (DMSO-d6): delta 7.84-7.22 (m, 4H); 7.22 (d, 2H, J=9Hz); 7.13 (d, 2H, J=9Hz); 5.50 (s, 2H); 3.77 (s, 3H); 3.75 (s, 3H); 3.55 (s, 3H); 2.67 (t, 2H, J=7Hz); 1.67 (t of q, 2H, J=7,7Hz); 0.88 (t, 3H, J=7Hz).

Statistics shows that 2-Propyl-1H-imidazole-4,5-dicarboxylic acid dimethyl ester is playing an increasingly important role. we look forward to future research findings about 124750-59-0.

Reference:
Patent; E. I. Du Pont de Nemours and Company; US5128355; (1992); A;,
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