Tag: M.W=200-300

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. 84946-20-3, name is 2-Chloro-1-(4-fluorobenzyl)-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., 84946-20-3

A mixture of 14 2-chloro-1-(4-fluorobenzyl)-1H-benzo[d]imidazole (2) (261mg, 1mmol) and 133 tert-butyl 3-aminopyrrolidine-1-carboxylate (370muL, 2mmol) in NMP (2mL) was heated at 180C under microwave for 60min. After cooling down to room temperature, the mixture was treated with a saturated 134 NaHCO3 solution and extracted with EtOAc. The combined organic phases was washed with water (2 times), dried over Na2SO4, and evaporated in vacuo. The crude residue was purified by silica gel flash column chromatography to afford the 135 title compound 18 (168mg, 54%). 1H NMR (300MHz, CDCl3) delta=7.53 (d, J=7.8Hz, 1H), 7.18-7.05 (m, 3H), 7.05-6.91 (m, 4H), 5.20 (s, 2H), 3.77-3.60 (m, 3H), 3.54 (ddd, J=9.7, 7.9, 6.2Hz, 1H), 3.26 (dd, J=9.4, 4.1Hz, 1H), 2.25 (br s, 2H), 2.18-2.06 (m, 1H), 1.79-1.65 (m, 1H)ppm. 13C NMR (75MHz, CDCl3) delta=162.11 (d, J=246.1Hz), 156.76, 142.16, 135.93, 132.52 (d, J=3.1Hz), 127.43 (d, J=8.0Hz), 121.98, 120.25, 116.76, 115.87 (d, J=21.6Hz), 108.28, 58.73, 51.21, 48.95, 47.08, 34.70ppm. HRMS m/z [M+H]+ calcd for C18H20FN4: 311.1666, found: 311.1662.

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; Tian, Junjun; Vandermosten, Leen; Peigneur, Steve; Moreels, Lien; Rozenski, Jef; Tytgat, Jan; Herdewijn, Piet; Van den Steen, Philippe E.; De Jonghe, Steven; Bioorganic and Medicinal Chemistry; vol. 25; 24; (2017); p. 6332 – 6344;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 1450-93-7, name is 1H-imidazol-2-amine sulfate(2:1), 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. 1450-93-7

2-Aminoimidazole sulfate (1.53 g) is dissolved in 0.97 mL of concentrated HCl, 1 mL of water, and 3 mL of acetic acid. The resulting solution is cooled to 0 C. A solution of 799 mg of NaNO2 in 2 mL of water is added dropwise, and the internal temperature is maintained below 5 C. The resulting yellow-brown solution is stirred for 30 minutes at 0 C. In a separate flask equipped with a mechanical stirrer a mixture of 1.65 g of 1,4-diallyl-1,2,3,4-tetrahydroquinoxaline, 1.9 g of sodium acetate and 10 mL of acetic acid is cooled to 0 C. The diazonium solution is added slowly to this slurry while stirring. After the addition is complete, the resulting red suspension is stirred for 1 hour at 0 C. The dark reaction mixture is poured into a beaker containing 10 g of ice. Aqueous NaOH (20%) is added to the suspension slowly until pH 6.5 is reached. The mixture is filtered and the dark solid is dried. (E)-6-((1H-imidazol-2-yl)diazenyl)-1,4-diallyl-1,2,3,4-tetrahydroquinoxaline (2.3 g) is used in the next step without further purification.

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 1450-93-7.

Reference:
Patent; The Procter & Gamble Company; MURPHY, Bryan Patrick; ZHANG, Guiru; ZHAO, Jielu; (32 pag.)US2018/72970; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 1450-93-7, name is 1H-imidazol-2-amine sulfate(2:1), 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. 1450-93-7

2-Aminoimidazole sulfate (1.53 g) is dissolved in 0.97 mL of concentrated HCl, 1 mL of water, and 3 mL of acetic acid. The resulting solution is cooled to 0 C. A solution of 799 mg of NaNO2 in 2 mL of water is added dropwise, and the internal temperature is maintained below 5 C. The resulting yellow-brown solution is stirred for 30 minutes at 0 C. In a separate flask equipped with a mechanical stirrer a mixture of 1.65 g of 1,4-diallyl-1,2,3,4-tetrahydroquinoxaline, 1.9 g of sodium acetate and 10 mL of acetic acid is cooled to 0 C. The diazonium solution is added slowly to this slurry while stirring. After the addition is complete, the resulting red suspension is stirred for 1 hour at 0 C. The dark reaction mixture is poured into a beaker containing 10 g of ice. Aqueous NaOH (20%) is added to the suspension slowly until pH 6.5 is reached. The mixture is filtered and the dark solid is dried. (E)-6-((1H-imidazol-2-yl)diazenyl)-1,4-diallyl-1,2,3,4-tetrahydroquinoxaline (2.3 g) is used in the next step without further purification.

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 1450-93-7.

Reference:
Patent; The Procter & Gamble Company; MURPHY, Bryan Patrick; ZHANG, Guiru; ZHAO, Jielu; (32 pag.)US2018/72970; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

144689-93-0, 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. 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, A new synthetic method of this compound is introduced below.

Toluene (180 L) is placed into a reactor and water (3.17 L) is added, followed by addition of ethyl-4-(1 -hydroxy-1 -methylethyl)-2-propylimidazole-5- carboxylate (18.0 Kg). The mass is stirred for about 10 minutes, heated to about 45C, and potassium carbonate (25.85 Kg) is added. The temperature of the mass is raised to about 65C and maintained for about 45 minutes. N-(triphenylmethyl)- 5-[4′-(bromomethyl)biphenyl-2-yl]tetrazole (48.9 Kg) and tetrabutylammonium bromide (4.82 Kg) are added at the same temperature and the mixture is stirred at 60-700C for 10 hours. Reaction completion is verified using thin layerchromatography (TLC). After the reaction is complete, the mass is washed with water (3*120 L) at about 500C. The mass is cooled to about 25C and toluene (468 L) and potassium tertiary-butoxide (12.6 Kg) is added, then the mass is maintained at the same temperature for about 1 hour. Water (0.85 L) is added and the mass is maintained at the same temperature for about 2 hours. Reaction completion is verified using TLC, then 5-methyl-2-oxo-(1 ,3-dioxolene-4-yl)methyl chloride (20 Kg), tetrabutylammonium bromide (4.82 Kg), and sodium carbonate (3.96 Kg) are added at 40-450C. The mass is stirred at about 55C for about 11 hours. After the reaction is complete, the mass is cooled to about 20C, water (540 L) is added and the pH is adjusted to about 6-7 by adding 10% aqueous HCI. The layers are separated. The aqueous layer is extracted with toluene (240 L). The organic layers are combined and washed with water (270 L). The solvent is distilled under reduced pressure. Acetone (189 L) is added to the residue and the mixture is heated to about 45C to produce a solution, then the solution is cooled to about 300C and maintained for about 20 minutes, followed by cooling to about 2C and maintaining for about 3 hours. The formed solid is filtered, washed with acetone (54 L), and dried for about 4 hours. The material obtained is re- crystallized from acetonitrile to yield 34.0 Kg of the title compound.

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; DR. REDDY’S LABORATORIES LTD.; DR. REDDY’S LABORATORIES, INC.; KOLLA, Naveen Kumar; MANNE, Nagaraju; NAREDLA, Anitha; SHINDE, Sachin Gulabrao; WO2011/14611; (2011); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

144689-93-0, Adding a certain compound to certain chemical reactions, such as: 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, 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 144689-93-0.

A mixture of ethyl-4-(1 -hydroxy-1 -methylethyl)-2-propylimidazole-5- carboxylate (5.0 g), potassium carbonate (5.75 g), and toluene (50 mL) is stirred at 45-500C for 45 minutes. N-(triphenylmethyl)-5-[4′-(bromomethyl)biphenyl-2- yl]tetrazole (13.2 g) and tetrabutylammonium bromide (1.3 g) are added and the mixture is stirred at 60-70 0C for 10 hours. The insoluble material is removed by filtration and the filtrate is washed with water (2*50 mL) at 60-700C. The filtrate is distilled under vacuum to produce a syrup. Methanol (25 mL) is added to the residue and stirred for 15 minutes at 25-35C. The mass is cooled to 0-5 0C and stirred at that temperature for 45 minutes. The precipitated solid is collected by filtration, washed with methanol (10 mL), and dried at 50-600C for 6 hours (yield 13.3 g).

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, Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DR. REDDY’S LABORATORIES LTD.; DR. REDDY’S LABORATORIES, INC.; KOLLA, Naveen Kumar; MANNE, Nagaraju; NAREDLA, Anitha; SHINDE, Sachin Gulabrao; WO2011/14611; (2011); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

3543-73-5, 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. 3543-73-5, name is Ethyl 4-(5-amino-1-methyl-1H-benzo[d]imidazol-2-yl)butanoate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 81.3 g (650.6 mmol) 2-bromoethanol, 1 g potassium iodide and 100 g water was added 17.0 g (65 mmol) compound (6). The reaction mixture was heated to 65-70 C. and held at this temperature for 8 h to 12 h. The pH value of the solution was held between 4.2-5.5 during this period by dropwise addition of a solution of 20.0 g (151.4 mmol) diammonium hydrogen phosphate in 35 g water. The control of pH over the duration of the reaction was effected through use of a pH electrode. The conversion was followed by HPLC. The reaction was continued until the fraction of compound (7A) was ?1.5%. Thereby ca. 8% of compound (7B) had formed and the proportion of compound (7) was ca. 87%. The reaction mixture was subsequently concentrated to dryness at ca. 55-60 C. under vacuum. To the residue was added 150 g water and, preferably with an alkali metal carbonate, the pH value adjusted to ca. 8.5. The desired product (7) was extracted with 200 g methylene chloride or 225 g chloroform, and the organic phase subsequently washed with 60-80 g water. The organic phase was then concentrated to dryness and the remaining oil or already crystalline residue dissolved in 200 g ethyl acetate or alternatively in 60 g acetonitrile. Compound (7) crystallised at ca. 5 C. and was filtered under suction, washed with 20 g cold ethyl acetate or alternatively with 15 g cold acetonitrile and dried at 60-70 C. The yield of compound (7) was 18.3 g (52.4 mmol) with a content of ?98.2% (80.5% of theory). The crude contained ?0.6% compound ( 7A) and compound (7B) respectively as well as <0.15% of compound (7C). The crude product obtained was recrystallized from ethyl acetate, or alternatively from acetonitrile, toluene, propan-2-ol, tetrahydrofuran, acetone, isopopyl acetate or water, prior to further conversion to compound ( 8). Thereby the yield of compound (7) was 17.2 g (94.0% recrystallization yield) with a content of >99.2%, wherein compound (7A) was removed below a content of 0.2% and compound (7B) below 0.3%. Through the course of the reaction, the content of compound (7C) was kept below 0.15%, as this compound can only poorly be removed by recrystallization from the above described solvents. The overall yield of this step was 76.5% of theory and was thus ca. 12.5% higher than that described in the procedure using ethylene oxide as according to DD34727 and ca. 31% higher in comparison to the favoured procedure of WO2011079193 involving addition of Huenig’s base.

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; Heyl Chemisch-pharmazeutische Fabrik GmbH & Co. KG; Frey, Michael; Walther, Dirk-Detlef; US2014/31560; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

The chemical industry reduces the impact on the environment during synthesis 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, I believe this compound will play a more active role in future production and life. 641571-11-1

0 ~ 5 ,will3- (4-methyl-1H-1-imidazolyl) -5-trifluoromethylaniline(24.1 g, 0.1 mol),Di-tert-butyl dicarbonate (21.8 g, 0.1 mol)And 200 mL of dichloromethane were added to a three-necked reaction flask,Triethylamine (28.5 g, 0.15 mol) was added dropwise with stirring,After that,Heating up to 25 ~ 35 ,Reaction for 12 hours,TLC detection,To the raw material reaction completely.The solvent was removed under reduced pressure,The resulting residue was recrystallized from ethyl acetate to give a white solidN- [3- (4-methyl-1H-1-imidazolyl) -5-trifluoromethylbenzene] tert-butoxycarbonylamine (III)(Tert-butoxycarbonyl protected compound of formula II), 29.5 g,Yield 86.5%.

The chemical industry reduces the impact on the environment during synthesis 641571-11-1. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Suzhou Lixin Pharmaceutical Co., Ltd.; Xu Xuenong; Bao Zhijian; Su Jian; Xue Jia; Gu Xinyu; Huang Dongliang; Chen Wei; Wang Zhe; (6 pag.)CN107188887; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

641571-11-1, Name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, 641571-11-1, 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.

A mixture of 3 (100 mg, 0.41 mmol), p-toluic acid (42) (56 mg, 0.41 mmol), HATU (312 mg, 0.82 mmol) and DIEA (207 mg, 1 .6 mmol) in DMF (2 mL) was heated at 60 C overnight. After cooling, the reaction was directly purified by reverse prep-HPLC andthen silica gel prep-TLC to give 4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5- (trifluoromethyl)phenyl)benzamide (21 mg, 14%) as an off-white solid.

Statistics shows that 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline is playing an increasingly important role. we look forward to future research findings about 641571-11-1.

Reference:
Patent; CARDIO THERAPEUTICS PTY LTD; TREUTLEIN, Herbert; ZENG, Jun; DIXON, Ian; JAMES, Ian; PALMER, James T; (169 pag.)WO2018/165718; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A common heterocyclic compound, 152628-03-0, name is 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid, molecular formula is C12H14N2O2, 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. 152628-03-0.

Methyl-6-carboxybenzimidazole 5. 00 kg, methylene chloride 15. 00 kg A solution of 3. 28 kg of thionyl chloride was added dropwise under stirring at 25 C with stirring. Reaction 1 hour, spare

The synthetic route of 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WEITE(Hunan)Pharmaceutical co.,ltd,; he, liang; Luo, Hui; Mo, Wei; (9 pag.)CN105237457; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

The chemical industry reduces the impact on the environment during synthesis 152628-03-0, name is 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid, I believe this compound will play a more active role in future production and life. 152628-03-0

Example 1:Orthophosphoric acid (210 gms) was taken in round bottomed flask and Rho205 (210 gms) was added in portions with vigorous stirring. (Note: Sharp increase in temperature > 200 C). The above mass is allowed to cool to 70 C and 2-n-propyl- 4-methyl-benzimidazole-6-carboxylic acid (70 gms, 0.321 mol) was added slowly. Then N-methylbenzene-l,2-diamine hydrochloride (62.3 gms, 0.321 mol) was added in small portions at same temperature and then the temperature was raised to 125-130 C. After completion, reaction was quenched with ice cold water (1 Lt), adjusted pH of the reaction mixture to 9-10 by the addition of aqueous ammonia solution. Obtained solid was filtered and washed with cold water until the pH of the filtrate becomes neutral. Then the crude solid was washed with hot water until colorless filtrate was observed. The crude solid was boiled in ethyl acetate (700 ml) for 2-3 hrs. The reaction mass was cooled and the suspension was filtered off and dried to yield 2-n-propyl-4-methyl-6-(l-methylbenzimidazol-2-yl)-lH- benzimidazole (V) (80 gms, Yield : 82 %).

The chemical industry reduces the impact on the environment during synthesis 152628-03-0. I believe this compound will play a more active role in future production and life.

Reference:
Patent; OGENE SYSTEMS (I) PVT LTD; LAKKOJU, Chakrapani; KONETI, Naga Raju; KOKKALLA, Sridhar; MALLELA, Sambhu Prasad Sarma; BOYAPATI, Nanoranjan Choudary; WO2012/28925; (2012); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem