Month: May 2021

Some common heterocyclic compound, 37619-25-3, name is Methyl 1H-benzo[d]imidazole-4-carboxylate, molecular formula is C9H8N2O2, 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. Recommanded Product: 37619-25-3

Methyl 1H-benzimidazole-4-carboxylate (315 mg) was dissolved in conc. sulfuric acid (3 mL), and the solutionwas stirred on ice bath. A small amount of potassium nitrate (199 mg) was added portion-wise, the solution was stirredat room temperature for 4 hours. The reaction mixture was poured into ice, alkalified with 3N aqueous sodium hydroxidesolution under stirring on ice bath, and extracted with ethyl acetate. The ethyl acetate layer was washed sequentiallywith water and brine, dried over anhydrous magnesium sulfate. The titled compound (334 mg) was obtained as colorlesspowder after distilling off a solvent under reduced pressure.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 37619-25-3, its application will become more common.

Reference:
Patent; Nippon Shinyaku Co., Ltd.; OTSU, Hironori; EP2746265; (2015); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 50257-40-4,Some common heterocyclic compound, 50257-40-4, name is 1-((2,4,6-Triisopropylphenyl)sulfonyl)-1H-imidazole, molecular formula is C18H26N2O2S, 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.

To a stirred suspension of NaH (60percent in oil dispersion) (2.9 g, 72 mmol) in dry THF (240 mL) at 0C was added in portions 7 (3.8 g, 24 mmol), followed by 2,4,6-triisopropyl-benzenesulfonylimidazole (20 g, 60 mmol), and the whole mixture was then stirred for 3 h. Cold H2O (100 mL) was added, and the resulting mixture was extracted with EtOAc (3 × 40 mL). The combined extracts were washed with brine (50 mL) and then dried (anhydrous Na2SO4). Evaporation of the solvent gave the crude product, which contains 12 and its regioisomer 13 with a ratio of 3:1. The mixture was purified by flash chromatography on silica gel (hexane/EtOAc, 50:1) to afford 12 and 13. For 12 (4.1g, 41percent yield; colorless oil): [alpha]D20 +2.0 (c = 1.00, CH2Cl2); 94.6percent ee; 1H NMR (300 MHz, CDCl3): delta 1.04 (t, J = 7.5 Hz, 3 H), 1.22-1.29 (m, 18 H), 2.01-2.08 (m, 2 H), 2.60-2.70 (m, 2 H), 2.81 (dd, J = 2.55, 4.81 Hz, 1 H), 2.90-2.93 (m, 2 H), 3.20-3.28 (m, 1 H), 4.12-4.16 (m, 2 H), 4.50-4.54 (m, 1 H), 7.18 (s, 2 H); 13C NMR (75 MHz, CDCl3): delta 12.3, 14.0, 23.0, 23.6, 24.7, 24.8, 29.8, 34.3, 45.5, 52.4, 72.8, 79.4, 85.2, 123.8, 130.7, 150.6, 153.7; HRMS (ESI): m/z [M+Na]+ calcd for C23H34O4SNa: 429.2070; found: 429.2073. For 13 (1.3g, 14percent yield; colorless oil): 1H NMR (400 MHz, CDCl3): delta 1.08 (t, J =7.5 Hz, 3H), 1.25-1.28 (m, 18H), 2.07-2.26 (m, 3H), 2.52-2.61 (m, 1H), 2.85-2.99 (m, 1H), 3.18-3.28 (m, 2H), 4.03-4.22 (m, 3H), 4.39 (dd, J = 3.81, 11.42 Hz, 1H), 7.20 (s, 2H); 13C NMR (100 MHz, CDCl3): delta 12.4, 14.0, 19.1, 23.7, 24.8, 24.8, 29.8, 34.4, 53.5, 54.7, 67.1, 73.1, 84.9, 124.0, 129.1, 151.0, 154.1; HRMS (ESI): m/z [M+Na]+ calcd for C23H34O4SNa: 429.2070; found: 429.2073. The enantiomeric excess of 12 was determined by chiral HPLC analysis (column, Chiralpak AD-H, 4.6 mm × 250mm, n-hexane / i-PrOH = 97:3; flow rate: 0.5 mL/min, lambda = 230nm). The retention times corresponding to 12 and its enantiomer are 12.8 min and 10.2 min, respectively.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-((2,4,6-Triisopropylphenyl)sulfonyl)-1H-imidazole, its application will become more common.

Reference:
Article; Xu, Kai; Zhao, Shuai; Xu, Jia-Kuan; Shan, Ming-Wei; Yu, Jia-Li; Wang, Yu-Bo; Zhang, Cheng-Fang; Chen, Xin; Synthetic Communications; vol. 47; 20; (2017); p. 1848 – 1853;,
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. 31250-80-3, name is 1-Benzyl-2,4,5-tribromo-1H-imidazole, A new synthetic method of this compound is introduced below., HPLC of Formula: C10H7Br3N2

Reflux a mixture of [1-BENZYL-2,] 4, [5-TRIBROMOIMIDAZOLE] (1.043 g, 2.42 mmol), 2,4- difluorophenyl boronic acid (0.682 g, 4.32 mmol), palladium acetate (0.027 g, 0.12 mmol), R (+) -2, 2′-bis [(DI-P-TOLYL-PHOSPHINO) 1, 1′-BINAPHTHYL] (0.098 g, 0.14 mmol), 2 M sodium carbonate (3.6 [ML,] 4.83 mmol), methanol (3.6 [ML)] and toluene (36 mL) for [18] hours. Cool to ambient temperature and dilute with ethyl acetate. Wash with saturated sodium carbonate, saturated sodium chloride, dry with magnesium sulfate and purify the residue on silica gel eluting with hexane/ethyl acetate mixtures to provide [1-BENZYL-4,] 5- [DIBROMO-2- (2, 4-DIFLUORO-PHENYL)-LH-IMIDAZOLE] (0.39 g). MS [(ES+)] : [NILZ] = 461.1 (M+H) [+]

The synthetic route of 31250-80-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2004/14900; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

2080-75-3, name is 5-Methoxy-1H-benzo[d]imidazol-2(3H)-one, 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. SDS of cas: 2080-75-3

Intermediate 38:[0169] A mixture of intermediate 37 (3.6 g, 22 mmol) and 48% hydrogen iodide (30 mL) was heated to reflux (130C) and stirred for 12 h. The reaction mixture was neutralized to pH = 8 with aq NaOH and then extracted with EtOAc. The combined organic layers were dried over anhydrous Na2S04, concentrated under vacuum and purified by flash chromatography on silica gel column (elution with DCM/MeOH = 80: 1) to give 5-hydroxy-lH-benzo[cf]imidazol-2(3H)- one (intermediate 38) (16.9 g, 80%). HPLC: 99%, RT 1.377 min. MS (ESI) m/z 151.0 [M + H]+. mp: 186-187C

The synthetic route of 2080-75-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL; JIN, Jian; ROTH, Bryan; FRYE, Stephen; WO2012/3418; (2012); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 17450-34-9, name is Ethyl 2-(1-Imidazolyl)acetate, 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. Recommanded Product: 17450-34-9

Take the above compounds Intermediate 1 is 7.7g (0.05mol) was dissolved in 100mL of water, concentrated hydrochloric acid to adjust the pH value of 1.5, refluxed for 7h at 100 deg.] C, After completion of the reaction, the resultant reaction liquid was distilled under reduced pressure at 25 deg.] C directly to the not drop out of the droplet, was added 300 mL of acetone to give a white solid was filtered and recrystallized from isopropanol to give white crystals, i.e. intermediate compound 2;

The synthetic route of Ethyl 2-(1-Imidazolyl)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Atomic Medical Institute; Lin Jianguo; Peng Ying; Qiu Ling; Lv Gaochao; Li Ke; Luo Shineng; Zhao Xueyu; Wang Shanshan; (22 pag.)CN106749405; (2017); A;,
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. 857070-66-7, name is (2-Chloro-1H-benzo[d]imidazol-6-yl)methanol, A new synthetic method of this compound is introduced below., Application In Synthesis of (2-Chloro-1H-benzo[d]imidazol-6-yl)methanol

A mixture of b-3 (0.069 mol) and N-propylamino-morpholine (0.207 mol) was stirred at 125C for 4 hours, and then taken up in CH2C12/CH3OH. The organic layer was washed with a 10% solution OfK2CO3 in water, dried (over MgSO4), filtered and the solvent was evaporated until dryness. The residue (37 g) was purified by column chromatography over silica gel (eluent: CH2C12/CH3OH/NH4OH 90/10/0.5; 20-45mum). The pure fractions were collected and the solvent was evaporated, yielding 16.5g of intermediate b-4 (82%).

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; TIBOTEC PHARMACEUTICALS LTD; WO2006/136562; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 13750-81-7, 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. 13750-81-7, name is 1-Methyl-1H-imidazole-2-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 76A1 -Ethyl- lH-imidazole-2- carbaldehyde[00631] To a suspension of lH-imidazole-2- carbaldehyde (480 mg, 5 mmol) and potassium carbonate (936 mg, 6 mmol) in N, N-dimethylformamide (7 mL) was added iodoethane (829 mg, 6mmol) and the mixture was heated at 50 C for 5 hrs. Solvent was removed under reduced pressure. The residue was partitioned between water (30 mL) and ethyl acetate (30 mL). The aqueous layer was extracted with ethyl acetate (20 mLx3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated to give 1 -ethyl- lH-imidazole-2- carbaldehyde as light yellow oil (520 mg, yield 84%). 1H MR (400 MHz, CDC13) delta (ppm): 1.42- 1.46 (t, J= 7.2 Hz, 3H), 4.42-4.47 (q, 2H), 7.19 (s, IH), 7.29 (s, IH), 9.82 (s, IH). LC-MS (ESI) m/z: 125 (M+l)+.

The synthetic route of 1-Methyl-1H-imidazole-2-carbaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; CHU, Daniel; WO2011/130661; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 65039-05-6, A common heterocyclic compound, 65039-05-6, name is 1-Butyl-3-methylimidazolium iodide, molecular formula is C8H15IN2, 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 preparation of BiOI microspheres was carried out bysolvothermal synthesis. All reagents used were of analytical grade (AR) and used as received without additional purification. 1 mmolof bismuth nitrate pentahydrate [Bi(NO3)3.5H2O] (Sigma-Aldrich,99.0%) was dissolved in ethylene glycol (10 mL, Merck 99.5%) andpoured in a solution of 10 mL of ethylene glycol containing 1 mmolof KI (99.0% Merck). The mixture was stirred at room temperaturefor 30 min and then transferred to a 23 mL Teflon autoclave reactor.The autoclave was heated at 126 C (at autogenous pressure) for18 h andfinally cooled to room temperature. Thefinal productswere separated by vacuumfiltration and extensively washed usingdistilled water and absolute ethanol (Merck, 99.5% v/v). Thematerial obtained was dried at 60 C for 24 h. The same procedurewas used to synthesize BiOI using ionic liquid 1-butyl-3-methylimidazolium iodide ([bmim]I) as an iodide source.

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; Mera, Adriana C.; Contreras, David; Escalona, Nestor; Mansilla, Hector D.; Journal of Photochemistry and Photobiology A: Chemistry; vol. 318; (2016); p. 71 – 76;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 253453-91-7, 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. 253453-91-7 name is 2-Chloro-1-methyl-1H-imidazole, 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.

Step C: (2-Chloro-3-methyl-3H-imidazol-4-yl)-(4-chloro-phenyl)-methanone. To a 1-L, three-necked, round-bottomed flask equipped with a magnetic stirrer, nitrogen inlet and an addition funnel was added 2-chloro-1-methyl-1H-imidazole (15 g, 0.128 mol) and THF (250 mL). The reaction mixture was cooled to -78 C. and n-BuLi (2.5 M in hexanes, 54 mL, 0.135 mol) was added. The pale yellow suspension that formed was stirred for 1 h and a solution of 4-chloro-N-methoxy-N-methyl-benzamide (27 g, 0.135 mol) in THF (50 mL) was then added dropwise. After the addition was complete, the cooling bath was removed and the reaction was allowed to warm to rt. The reaction mixture was quenched with satd. aq. NH4Cl (150 mL), transferred to a separatory funnel, and extracted with EtOAc (1.5 L). The organic layer was washed with water, brine and dried over anhydrous Na2SO4. After filtration, the solvents were evaporated under reduced pressure to yield the product as a crystalline solid. Recrystallization from EtOAc-hexanes afforded the desired ketone (31.2 g, 97%) as a white crystalline solid. mp 173-174 C. IR (film): 1639, 1589, 1517, 1395, 1377, 1253, 1186, 902, 841, 756, 738, 695, 676 cm-1. 1H NMR (400 MHz, CDCl3): delta7.78 (d, J=8.6 Hz, 2H), 7.44 (s, 1H), 7.44 (d, J=8.6 Hz, 2H), 3.97 (s, 3H). 13C NMR (100 MHz, CDCl3): delta183.3, 140.3, 139.5, 139.2, 136.3, 131.2, 130.4, 128.9, 33.5. HRMS (EI): m/z calcd for C11H9Cl2N2O [M+H]+, 255.0092; found, 255.0104. Anal. Calcd for C11H8Cl2N2O: C, 51.8; H, 3.06; N, 10.93. Found: C, 52.08; H, 3.16; N, 10.90.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-1-methyl-1H-imidazole, and friends who are interested can also refer to it.

Reference:
Patent; Jones, Todd K.; Mani, Neelakandha; US2005/250948; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 26530-93-8,Some common heterocyclic compound, 26530-93-8, name is 1-Methyl-1H-benzo[d]imidazol-6-amine, molecular formula is C8H9N3, 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.

Example No. 148Preparation of (8-Methoxy-2H-pyrazolo [3 , 4-c] quinolin-4-yl) – (3- methyl-3H-benzoimidazol-5-yl) -amine4-chloro-8-methoxy-2- (4-methoxybenzyl) -2H-pyrazolo [3,4- c]quinoline (0.16 mmol) and l-methyl-lH-benzoimidazol-6-amine (2 eq.,0.3 mmol) were suspended in MeOH (dry, 3mL) in a microwave vial (2-5mL) , HC1 in dioxane (4M, 3 drops) was added. The reaction mixture was irradiated in a microwave reactor for 5 min at 140 °C. The reaction mixture was evaporated and used without further purification. The residue was dissolved in TFA (3mL) . The reaction mixture was irradiated in a microwave reactor for 5 min at 140°C. The reaction mixture was concentrated and purified by semi- preparative HPLC-MS and freeze dried from water/t-BuOH 4/1. exact mass: 344.1599 g/mol HPLC-MS: analytical method Brt: 1.518 min – found mass: 345.1 (m/z+H)

The synthetic route of 26530-93-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ORIGENIS GMBH; ALMSTETTER, Michael; THORMANN, Michael; TREML, Andreas; KOESTLER, Roland; YEHIA, Nasser; WO2012/143143; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem