Month: September 2021

A common heterocyclic compound, 15788-16-6, name is 1H-Benzo[d]imidazole-5-carboxylic acid, molecular formula is C8H6N2O2, 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. 15788-16-6.

Preparation 26 Methyl 5-benzimidazolecarboxylate A mixture of 10 g of 5-benzimidazolecarboxylic acid, 150 ml of methanol and 100 ml of a 4N solution of hydrogen chloride in 1,4-dioxane was agitated ultrasonically for 4 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, after which 300 ml of methanol and 3.5 g of lithium borohydride were added to the residue and the mixture was stirred for 1 hour. The solvent was then removed by evaporation under reduced pressure and the residue was mixed with an aqueous solution of sodium chloride, after which it was extracted with ethyl acetate. The solvent was removed by distillation under reduced pressure, to give 5.44 g of the title compound, melting at 136-138 C.

The synthetic route of 1H-Benzo[d]imidazole-5-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sankyo Company, Limited; US5886014; (1999); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

The chemical industry reduces the impact on the environment during synthesis 2849-93-6, name is 1H-Benzimidazole-2-carboxylic acid, I believe this compound will play a more active role in future production and life. 2849-93-6

At room temperature,3.0 g (18.6 mmol) of 1H-benzimidazole-2-carboxylic acid was placed in a 100 mL eggplant type flask,Add 30mL of thionyl chloride, 79 reflux reaction 4h, after the end of the reaction evaporated solvent.Add 30mL ammonia water, 70 reaction 5h, cooling the reaction solution,Filtration of yellow solid, dry. The yield was 55%.

The chemical industry reduces the impact on the environment during synthesis 2849-93-6. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Shenyang Pharmaceutical University; Zhao Linxiang; Liu Dan; Li Kun; Ma Tianyi; Jing Yongkui; (13 pag.)CN107118249; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 496-46-8, 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. 496-46-8, name is Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

tetraallylglycoluril A three-neck 100 ml flask was flushed with argon. Anhydrous DMSO (40 ml) was added and glycoluril (1.42 g, 10 mmol) was dissolved. Then potassium tert-butoxide (5.62 g, 50 mmol) was gradually added and the mixture was further stirred for 1.0 h. Allyl bromide (7.0 ml, 80 mmol) was injected into the reaction mixture and the reaction was performed at 25C for 20 h. 500 ml aqueous solution of HCl (0.1 M) was added into the reaction mixture. 100 ml ethyl acetate was used to extract the mixture andthe organic phase was washed by saturated NaCl aqueous solution(100 ml) for three times. After being dried by MgSO4, the solventwas removed. 1.53 g target product was obtained after purifica-tion over silica column with the eluent of ethyl acetate/petroleumether (60-90C) (v/v, 3:2). All procedures were performed in argonatmosphere.

The synthetic route of Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Bingfeng; Li, Fengbo; Huang, Zhijun; Lu, Tao; Yuan, Guoqing; Applied Catalysis A: General; vol. 481; (2014); p. 54 – 63;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 3543-72-4, 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.

To a clean dry flask were charged Iron powder (85 g), Cone. HCI (12.5 ml), and 625 ml of methanol and stirred for 5 minutes at room temperature. The contents were heated to 60-65 C and maintained for 2 hours. At that temperature ammonium chloride solution was charged and maintained for 15 minutes and subsequently cooled to RT. Compound II (80g) was added and then the reaction mass was maintained at 60-65 C for 2h. The mass was cooled to room temperature, filtered and distilled. To the residue was charged water and The pH adjusted to 7-8 using sodium bicarbonate solution. The Aqueous layer is extracted with ethyl acetate and the organic layer is distilled out completely to the give the title compound as a solid (60 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-methyl-5-nitro-1H-benzo[d]imidazol-2-yl)butanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BIOPHORE INDIA PHARMACEUTICALS PVT. LTD.; PULLAGURLA, Manik Reddy; RANGISETTY, Jagadeesh Babu; PRESLEY, S., I., Davis; NAGARAPU, Radha; WO2012/7966; (2012); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 3012-80-4, name is 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde, 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 3012-80-4, Recommanded Product: 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde

General procedure: Benzimidazole 1 or 2 (1 mmol)was added to the mixture of TfOH (1 mL) or H2SO4 (2 mL) and arene (2-18 mmol). Reactionmixture was stirred at room temperature for the time as indicated in Table 3 or Scheme 2. Themixture was poured into ice water (30 mL). After extraction with CH2Cl2 (3 × 30 mL), thecombined extracts were consequently washed with water (50 mL), saturated aqueous solution ofNa2CO3 (30 mL), water (50 mL), dried with anhydrous Na2SO4 and evaporated in vacuo to givecrude products, which was subjected to chromatographic separation on silica gel using petroleumether/diethyl ether as an eluent.

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:
Article; Ryabukhin, Dmitry S.; Turdakov, Alexey N.; Soldatova, Natalia S.; Kompanets, Mikhail O.; Ivanov, Alexander Yu.; Boyarskaya, Irina A.; Vasilyev, Aleksander V.; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1962 – 1973;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

137049-00-4, Name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, 137049-00-4, 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.

To a solution of intermediate 2.103 (20. mg, 0.078 mmol) and triethylamine (30 muL, 0.2 mmol) in dichloromethane (0.5 mL) at 0 C was added 1-methyl-1H-imidazole-4- sulfonyl chloride (21 mg, 0.12 mmol). The resulting mixture was stirred for 18 h, then diluted with wet DMSO (1 mL), filtered through Celite and purified via mass-directed isolation using ultra-performance liquid chromatography (18 mg, 57% yield).1H NMR (500 MHz, (0494) Acetonitrile-d3) d 8.61 (s, 1H), 7.73 (s, 1H), 7.69 (dd, J = 11.8, 2.4 Hz, 1H), 7.57 (d, J = 1.4 Hz, 1H), 7.37 (t, J = 8.6 Hz, 1H), 7.26- 7.18 (m, 1H), 3.85- 3.77 (m, 1H), 3.73 (s, 3H), 3.64 (d, J = 12.0 Hz, 1H), 2.67 (t, J = 11.2 Hz, 1H), 2.62- 2.47 (m, 2H), 1.85- 1.76 (m, 1H), 1.59 (qt, J = 12.5, 4.0 Hz, 1H), 1.53- 1.41 (m, 1H); AMM 423.0678 (ESI) m/z [calc for (0495) C16H18ClFN4O3SNa (M+Na)+ 423.0670].

Statistics shows that 1-Methyl-1H-imidazole-4-sulfonyl chloride is playing an increasingly important role. we look forward to future research findings about 137049-00-4.

Reference:
Patent; THE TRUSTEES OF THE UNIVERSITY OF PENNSYLVANIA; VAL-CHUM, LIMITED PARTNERSHIP; GRENIER, Melissa Carey; SMITH, Amos B., III; FINZI, Andres; DING, Shilei; CHAPLEAU, Jean-Philippe; (240 pag.)WO2020/28482; (2020); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, 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. Recommanded Product: 144689-93-0

An eggplant flask was charged with 5- (1-hydroxy-1-methylethyl) -2-propyl-3H-imidazole-4-carboxylic acid ethyl ester (10 g, 41.7 mmol; imidazole derivative (compound of formula (4b)), 4-bromobenzyl bromide (10.8 g, 43 mmol; dihalogen compound),Dimethylacetamide (40 ml; first reaction solvent (DMA)) was added to a mixture of potassium carbonate (7.1 g, 51.6 mmol; base) and stirred for 48 hours. After the reaction, water (120 mL) was added to the reaction solution and stirred. The precipitated crystals were filtered and recrystallized from ethyl acetate to give 3- (4-bromobenzyl) -5- (1-hydroxy-1-methylethyl) -2-propyl-3H-imidazole-4-carboxylic acid ethyl ester(A halogenated imidazole derivative (compound of the formula (1b))) 8 g (yield 47%).

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

Reference:
Patent; Tokuyama Corporation; Sekine, Masahiko; Tanaka, Kenji; (31 pag.)JP2018/154611; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 33529-02-1, 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 33529-02-1 as follows.

In einem Autoklaven wurden 0,25 Mol 1-Decylimidazol, welches durch die Radziszewski-Reaktion aus Glyoxal, Formaldehyd, Ammoniak und 1-Decylamin zugaenglich ist (siehe Ullmann’s Encyclopedia of Industrial Chemistry, 6th edition, 2000 electronic release, Chapter “IMIDAZOLE AND DERIVATIVES – Production), und 0,3 Mol Dimethylcarbonat in 100 ml Methanol zusammen mit 1,5 g Kaliumcarbonat und 0,1 g 18-Krone-6 12 Stunden auf 135C erhitzt. Nach dem Abkuehlen wurde der Reaktionsaustrag filtriert und mit 150 ml 50%iger waessriger Tetrafluoroborsaeure (Fa. Acros) versetzt. Nun wurde fuer eine Stunde unter Ruehren auf 50C erwaermt und anschliebetaend die waessrige Phase abgetrennt. Die verbleibende organische Phase wurde erneut mit 100 ml 50 %iger waessriger Tetrafluoroborsaeure versetzt, fuer eine weitere Stunde unter Ruehren auf 50C erwaermt und die waessrige Phase abgetrennt. Der organische Rueckstand wurde nun zweimal mit Cyclohexan extrahiert und danach im Vakuum bei 80C von Loesungsmittelresten befreit. Es wurden 0,16 Mol 1-Decyl-3-methylimidazolium-tetrafluoroborat erhalten, was einer Ausbeute von 64 % entspricht.

According to the analysis of related databases, 33529-02-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BASF AKTIENGESELLSCHAFT; EP1398318; (2004); 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. 124750-59-0, name is 2-Propyl-1H-imidazole-4,5-dicarboxylic acid dimethyl ester belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Formula: C10H14N2O4

A mixture of dimethyl-2-propylimidazole-4,5-dicarboxylate compound of formula-2a (100 grams), 4-[2-(trityltetrazol-5-yl)phenyl]benzyl bromide compound of formula-3 (296 grams), potassium carbonate (119 grams) in dimethyl formamide (100 ml) and acetone (500 ml) was heated to reflux temperature. The reaction mixture was stirred up to reaction completion and solvent was distilled off completely from the reaction mixture under reduced pressure at below 50C. The reaction mixture was cooled to 25-300C, acetone (150 ml) and water (1000 ml) were added to it then stirred for 60 minutes. The obtained solid was filtered, washed with water and then the wet solid was recrystallized from acetone to provide the title compound.Yield: 285 grams;Purity by HPLC: 98.15%

The synthetic route of 124750-59-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MSN LABORATORIES LIMITED; SATYANARAYANA REDDY, Manne; NAGARAJU, Chakilam; THIRUMALAI RAJAN, Srinivasan; KODANDA RAMPRASAD, Achampeta; RAMA SUBBA REDDY, Karamala; WO2011/21224; (2011); A2;,
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. 17289-26-8, name is 1-Methyl-1H-imidazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., name: 1-Methyl-1H-imidazole-4-carbaldehyde

Synthesis of 4-((1R,5S,9r)-9-methoxy-3-((1-methyl-1H-imidazol-4-yl)methyl)-3-azabicyclo[3.3.1]nonan-9-yl)picolinamide hydrochloride To a suspension of 4-((1R,5S,9r)-9-methoxy-3-azabicyclo[3.3.1]nonan-9-yl)picolinamide hydrochloride (100 mg, 0.32 mmol), 1-methyl-1H-imidazole-4-carboxaldehyde (70 mg, 0.64 mmol) and acetic acid (37 muL, 0.64 mmol) in dichloromethane (5 mL) was added sodium triacetoxyborohydride (203 mg, 0.96 mmol) at ambient temperature. After stirring for 16 hours, the reaction was quenched with saturated aqueous sodium hydrogen carbonate solution and extracted with dichloromethane (*3). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica column chromatography, eluting with 2-10% methanol in dichloromethane to yield 4-((1R,5S,9r)-9-methoxy-3-((1-methyl-1H-imidazol-4-yl)methyl)-3-azabicyclo[3.3.1]nonan-9-yl)picolinamide (84 mg, 71% yield). To 4-((1R,5S,9r)-9-methoxy-3-((1-methyl-1H-imidazol-4-yl)methyl)-3-azabicyclo[3.3.1]nonan-9-yl)picolinamide (125 mg, 0.34 mmol) in ethyl acetate (10 mL) and dichloromethane (2 mL), was added 2M HCl in diethyl ether (0.17 mL, 0.34 mmol). The solvent was removed under reduced pressure. The resulting solid was triturated with diethyl ether and the liquors decanted. The solid was dried, dissolved in water and freeze-dried to yield 4-((1R,5S,9r)-9-methoxy-3-((1-methyl-1H-imidazol-4-yl)methyl)-3-azabicyclo[3.3.1]nonan-9-yl)picolinamide hydrochloride (83 mg, 60% yield). [M+H]+ 370.15. 1H NMR (400 MHz, D2O): 8.60 (d, 1H), 8.21 (s, 1H), 7.98 (s, 1H), 7.60 (d, 1H), 7.54 (s, 1H), 4.33 (s, 2H), 3.74 (s, 3H), 3.61 (d, 2H), 3.48 (d, 2H), 2.92 (s, 2H), 2.67 (s, 3H), 1.85-1.68 (m, 2H), 1.56-1.42 (m, 4H).

According to the analysis of related databases, 17289-26-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Alkermes, Inc.; Wynn, Thomas Andrew; Alvarez, Juan C.; Moustakas, Demetri Theodore; Haeberlein, Markus; Pennington, Lewis D.; US2019/241524; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem