Tag: M.W=100-200

Electric Literature of 1632-83-3,Some common heterocyclic compound, 1632-83-3, name is 1-Methylbenzimidazole, molecular formula is C8H8N2, 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.

General procedure: The product 7h is a representative reaction. To a screw-cappedvial (5 mL) containing Ni(COD)2 (14 mg, 0.05 mmol), IMes (14 mg, 0.05 mmol),benzimidazole (66 mg, 0.50 mmol), and potassium tert-butoxide (5.6 mg, 0.05 mmol)was added toluene (1.0 mL) followed by the addition of 1,5-cyclooctadiene (43 mg,0.04 mmol) in a glove box atmosphere. The reaction vial was closed and heated at 80o C for 2 hours outside of the glove box. The resulting mixture was filtered throughCelite and washed with dichloromethane. The filtrate solution was concentrated invacuo to afford the crude product, which was further purified by columnchromatography using hexane/ethyl acetate (4:1 v/v) as eluent to furnish(E)-2-(cyclooctenyl)-1-methyl-benzimidazole 7h (117 mg) in 97% yield.The compound 7i was synthesized via similar conditions (see Table 3)._(E)-2-(cyclooct-1-en-1-yl)-1-methyl-1H-benzo[d]imidazole (7h): 1H NMR (300MHz, CDCl3): delta 7.75-7.71 (m, 1H), 7.25-7.19 (m, 3H), 6.06 (t, J = 8.1, 1H), 3.72 (s,3H), 2.75-2.71 (m, 2H), 2.36 (dd, J = 8.1, 11.4, 2H), 1.66-1.59 (m, 8H). 13C NMR (75MHz, CDCl3): delta 155.6, 142.4, 136.1, 135.8, 131.6, 122.1, 121.8, 119.3, 109.2, 31.6,29.3, 29.0, 28.9, 26.9, 26.4, 26.1. HR-MS (EI): calculated for: [C16H20N2]+: 240.1626.Found: 240.1620.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Methylbenzimidazole, its application will become more common.

Reference:
Article; Lee, Wei-Chih; Shih, Wei-Chin; Wang, Ting-Hsuan; Liu, Yuhua; Yap, Glenn P.A.; Ong, Tiow-Gan; Tetrahedron; vol. 71; 26-27; (2015); p. 4460 – 4464;,
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. 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., Quality Control of 2-Chloro-1H-benzo[d]imidazole

(2) Synthesis of intermediate (C-2); [0080][Chem. 12] Intermediate (C-2); [0081] 2-Chloro-benzimidazole (20 g (131 mmol, trade name: 2-Chlorobenzimidazole, manufactured by Aldrich) and THF (150 mL) were placed in a 500-mL three-neck flask, and t-butoxy sodium (13.8 g (144 mmol)) was added thereto under ice cooling. The mixture was stirred at room temperature for 1 hour. Subsequently, a solution of methyl iodide (24.2 g (170 mmol)) and THF (30 mL) was dropped into the flask under ice cooling, and the resulting mixture was stirred at room temperature for 5 hours. The reaction solution wasextracted with chloroform, followed by drying over anhydrous sodium sulfate. Subsequently, the solvent was removed to obtain 18.6 g (yield: 85%) of an intermediate (C-2) (2- chloro-1 -methyl- lH-benzimidazole, white crystal) .

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; CANON KABUSHIKI KAISHA; MUTA, Hajime; SEKIGUCHI, Takeshi; ISHII, Ryuji; SUZUKI, Koichi; WO2011/122381; (2011); 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. 3034-38-6, name is 5-Nitro-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of 5-Nitro-1H-imidazole

5-Nitroimidazole (2) (1 g, 8.85 mmol) and dimethyl sulfate (1.2 mL) were added in dioxane (5 mL). Reaction mixture was refluxed for 2 h. The solvent was then evaporated under vacuum, and the oily acidic residue was neutralized by a NaHCO3 saturated aqueous solution. The formed solid and the aqueous solution were extracted with dichloromethane (3 x 5 mL). Mixture was dried with magnesium sulfate and organic solvent evaporated on vacuum, crude was purified using flash column chromatography (dichloromethane/ethylacetate; 97:3) to obtained 1-Methyl-5-nitro-1H-imidazole (4a) (0.92 g, 82%); m.p. 60 C.

The synthetic route of 3034-38-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Samant, Bhupesh S.; Sukhthankar, Mugdha G.; Bioorganic and Medicinal Chemistry Letters; vol. 21; 3; (2011); p. 1015 – 1018;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 116568-17-3, name is 1H-Benzo[d]imidazole-6-carboxamide, 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. category: imidazoles-derivatives

EXAMPLE 23 1-(6-{[(1S)-1-(3-Fluorophenyl)ethyl]amino}pyrazin-2-yl)-1H-benzimidazole-6 carboxamide: To a stirred mixture of 6-chloro-N-[(1S)-1-(3-fluorophenyl)ethyl]pyrazin-2-amine (242 mg, 0. 96 mmol) and 5-benzimidazole carboxamide (318 mg, 1. 97 mmol, 2, 1 eq) in 18 dimethylformamide (5 mL) was added cesium carbonate (460 mg, 1.41 mmol, 1.5 eq). This solution was then heated at 120C under a nitrogen atmosphere for 48 hours at which time a second amount of cesium carbonate (180 mg, 0. 6 eq) was added. The mixture was heated at 120C for a further 62 hours before being cooled to room temperature, diluted with chloroform (15 mL) and filtered, The filtrate was then concentrated in vacuo and subjected to silica column chromatography (stepwise gradient from dichloromethane to 9: 1 dichloromethane : methanol) to yield the 5-carboxamide product (100. 7 tng, 28%) along with the desired 6-carboxamide product (63.7 mg, 18%). ‘H NMR (d6-acetone, 300 MHz) No. 1.64 (3H, d, J = 6. 9 Hz), 2.76-2. 80 (2H, brm), 5.35 (1H, m), 6.93 Cm, m), 7. 29-7. 36 (3H, m), 7. 42 (1H, dm,/= 7. 7 I Iz), 7. 77 (1H, dd, J = 8.5, 0.5 Hz), 7.93 (1H, dd, 1. 7, 8. 5 Hz), 8.05 (1H, s), 8. 31 (1H, s), 8. 73 (1H, s), 8.40 (1H, dd, J = 0. 5, 1. 6 Hz). MS (c. i.) m/z 376 (M+, 89%).

The synthetic route of 1H-Benzo[d]imidazole-6-carboxamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CYTOPIA RESEARCH PTY LTD; WO2005/54230; (2005); 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. 25676-75-9, name is 4-Bromo-1-methylimidazole, A new synthetic method of this compound is introduced below., Product Details of 25676-75-9

General procedure for preparation of Compound 10-6: A solution of Compound 10-3 (169 mg, 0.3 mmol) in a mixture of dioane (10 mL)-H20 (1 mL), was added Compound 10-5 (55.8 mg, 0.3 mmol), Cs2C03 (195 mg, 0.6 mmol) and Pd(dppf)Cl2 (22 mg, 0.03 mmol) and heated under irradiation of M W at 130C for 30 min under N2. Catalyst was filtered through diatomite and concentrated in vacuum to give the crude product (100 mg, yield 61.3%).

The synthetic route of 25676-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC; CHEN, Huifen; CRAWFORD, Terry; MAGNUSON, Steven, R.; NDUBAKU, Chudi; WANG, Lan; WO2013/113669; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 7189-69-7, name is 1,1′-Sulfonyldiimidazole, 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 7189-69-7, Product Details of 7189-69-7

To a pre-washed (hexane) suspension of NaH (60% in mineraloil, 284 mg, 7.11 mmol) in dry DMF (10 mL), a soln of 7 (1.06 g,1.42 mmol) in dry DMF (15 mL) was slowly added under argonatmosphere at 0 C. The mixture was stirred at 0 C for 30 min,cooled to 30 C, treated with Im2SO2 (411.5 mg, 2.08 mmol) andfurther stirred at 30 C. After 1 h, TLC analysis (4:6 hexane-EtOAc) revealed the complete disappearance of the starting material.The reaction mixture was then cooled to 40 C, the excess ofNaH was destroyed by addition of MeOH (0.5 mL). After 10 min,Et2O (20 mL) and crushed iced-water were added. The organicphase was separated and the aqueous layer was extracted withEt2O (3 50 mL). The collected organic phases were dried, filtered,and concentrated under diminished pressure. Flash chromatographicpurification over silica gel of the reaction product (6:4 hexane-EtOAc) gave pure 8 (1.02 g, 83% yield) as a clear syrup; Rf 0.37(6:4 hexane-EtOAc), [a]D 13.6 (c 1.16, CHCl3); 1H NMR (CD3CN): d8.01 (dd, 1H, J2,4 1.3 Hz, Im-H2), 7.46 (dd, 1H, J2,5 0.9 Hz, J4,5 1.6 Hz,Im-H4), 7.40-7.24 (m, 15H, Ar-H), 7.01 (dd, 1H, Im-H5), 5.25 (dd,1H, J10,20 0.6 Hz, J20,30 2.3 Hz, H-20), 4.94 (d, 1H, H-10), 4.68, 4.48(AB system, 2H, JA,B 10.8 Hz, CH2Ph), 4.64, 4.49 (AB system, 2H,JA,B 11.8 Hz, CH2Ph), 4.56, 4.47 (AB system, 2H, JA,B 11.9 Hz, CH2Ph),4.35 (m, 2H, H-1, H-2), 4.20 (dt, 1H, J4,5 4.9 Hz, J5,6a = J5,6b 6.4 Hz,H-5), 4.03 (dd, 1H, J2,3 7.3 Hz, J3,4 1.9 Hz, H-3), 3.94 (m, 2H, H-6a,H-6b), 3.89 (dd, 1H, H-4), 3.70 (dd, 1H, J30,40 10.5 Hz, H-30), 3.68(m, 3H, H-40 , H-60a, H60b), 3.39 (m, 1H, H-50), 3.38, 3.35 (2s, each3H, 2 OMe-1), 1.35, 1.34, 1.32, 1.29 (4s, each 3H, 2 CMe2);13C NMR (CD3CN): d 139.3, 139.1, 138.4 (3 Ar-C), 138.1 (Im-C2),131.2 (Im-C4), 129.3-128.6 (Ar-CH), 119.7 (Im-C5), 110.5, 109.0(2 CMe2), 106.3 (C-1), 99.0 (C-10), 84.6 (C-20), 78.7 (C-4), 78.0

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

Reference:
Article; Guazzelli, Lorenzo; Catelani, Giorgio; D’Andrea, Felicia; Gragnani, Tiziana; Carbohydrate Research; vol. 388; 1; (2014); p. 44 – 49;,
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 17228-38-5 as follows. Safety of N-Methyl-1H-benzo[d]imidazol-2-amine

Example 2.03 can also be prepared as follows:(3R)-4-(2-Chloro-6-(1-((R)-S-methylsulfonimidoyl)cyclopropyl)pyrimidin-4-yl)-3-methylmorpholine (179 mg, 0.54 mmol), N-methyl-1H-benzo[d]imidazol-2-amine (159 mg, 1.08 mmol) and cesium carbonate (529 mg, 1.62 mmol) were suspended in DMA (2 ml) and sealed into a microwave tube. The reaction mixture was heated to 80 C. for 90 minutes in a microwave reactor and then cooled to RT. The reaction mixture was filtered and then purified by preparative HPLC, using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to afford a solid (55.0 mg). In an additional procedure: (R)-4-(2-Chloro-6-(1-((R)-S-methylsulfonimidoyl)cyclopropyl)pyrimidin-4-yl)-3-methylmorpholine (89 mg, 0.27 mmol), N-methyl-1H-benzo[d]imidazol-2-amine (79 mg, 0.54 mmol) and cesium carbonate (263 mg, 0.81 mmol) were suspended in DMA (2 ml) and sealed into a microwave tube. The reaction mixture was heated to 80 C. for 5 hours in a microwave reactor and then cooled to RT. The reaction mixture was filtered, and combined with the solid from the previous procedure and then purified by preparative HPLC using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated and the residue was purified by preparative HPLC using decreasingly polar mixtures of water (containing 0.1% formic acid) and MeCN as eluents. Fractions containing the desired compound were evaporated and the residue purified again by preparative HPLC using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to afford the title compound (38.4 mg, 32%); 1H NMR (400 MHz, DMSO-d6) 1.29 (3H, d), 1.52 (3H, m), 1.72-1.86 (1H, m), 3.02 (3H, s), 3.03 (3H, d), 3.26-3.33 (1H, m), 3.52 (1H, t), 3.66 (1H, d), 3.80 (1H, d), 4.01 (2H, m), 4.12 (1H, s, obscured by methanol peak), 4.51 (1H, s), 6.77 (1H, s), 6.98 (1H, t), 7.09 (1H, t), 7.25 (1H, d), 8.08 (1H, d), 8.71 (1H, d); m/z: (ES+) MH+, 442.16. Chiral HPLC: (HP1100 System 4, 20 mum Chiralpak AS (250 mm×4.6 mm) column eluting with iso-Hexane/IPA/TEA 70/30/0.1) Rf, 11.984 97.9%.

According to the analysis of related databases, 17228-38-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; US2011/306613; (2011); 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. 50995-95-4, name is 2-Propylimidazole, A new synthetic method of this compound is introduced below., Safety of 2-Propylimidazole

Add 2,4-dichloropyrimidine (3.000 g, 20.2 mmol), 2-propylimidazole (2.662 g, 24.2 mmol) and potassium carbonate (4.168 g, 30.3 mmol)Add it to a round bottom flask (100 mL), using acetonitrile (40 mL) as a solvent,The reaction was carried out at 50 C for 11 hours. TLC was followed until the reaction was complete,Cooled to room temperature, distilled under reduced pressure,Purification by column chromatography to obtain white solid intermediate III-7(1.453 g), yield: 32.4%.

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; Southwest University; Zhou Chenghe; Wang Ya; Li Ruixue; Wang Jie; Geng Rongxia; (21 pag.)CN110452224; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 570-22-9, A common heterocyclic compound, 570-22-9, name is 1H-Imidazole-4,5-dicarboxylic acid, molecular formula is C5H4N2O4, 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.

General procedure: The complex was synthesized by hydrothermal method. A mixture of Zn(NO3)2.6H2O (0.47 g; 1.6 mmol), H3idc (0.25 g, 1.6 mmol) and water (30 mL) was sealed in a 45 mL Parr brand teflon-linedacid digestion bomb and heated at 180 C for 5 days, and then cooled to room temperature at a rate of 5 C/h.

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; Erer, Hakan; Ye?ilel, Okan Zafer; ?ahin, Onur; Bueyuekguengoer, Orhan; Inorganica Chimica Acta; vol. 434; (2015); p. 14 – 23;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 615-16-7, The chemical industry reduces the impact on the environment during synthesis 615-16-7, name is 2-Hydroxybenzimidazole, I believe this compound will play a more active role in future production and life.

Step 1: (0389) 1H-benzimidazol-2(3H)-one 19-a (500 mg, 3.73 mmol) was added into anhydrous aluminum chloride (1.98 g, 14.9 mmol) and tetrachloroethane (3 ml). Chloroacetyl chloride (843 mg, 7.46 mmol) dissolved in tetrachloroethane (3 ml) was added dropwise thereto under ice bath followed by stirring at 100 C. for 1 hour. The mixture was cooled to room temperature, ice and 4N hydrochloric acid (20 ml) were added sequentially followed by stirring for 6 hours, the precipitated solid was filtered, the filter cake was slurried in isopropanol, filtered, and dried to give 19-b as an off-white solid (730 mg, yield: 93%). EI-MS (m/z): 210.

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-Hydroxybenzimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SHANGHAI INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF SCIENCES; SUZHOU VIGONVITA LIFE SCIENCES CO., LTD.; TOPHARMAN SHANDONG CO., LTD.; JIANG, Hualiang; WANG, Zhen; LI, Jianfeng; ZHANG, Rongxia; HE, Yang; LIU, Yongjian; BI, Minghao; LIU, Zheng; TIAN, Guanghui; CHEN, Weiming; YANG, Feipu; WU, Chunhui; WANG, Yu; JIANG, Xiangrui; YIN, Jingjing; WANG, Guan; SHEN, Jingshan; (70 pag.)US2017/158680; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem