Author: Jessica.F

Some common heterocyclic compound, 288-32-4, name is 1H-Imidazole, molecular formula is C3H4N2, 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. name: 1H-Imidazole

General procedure: NH-containing heterocycle (1.4 mmol) and DMF (2.0 mL) were added to a mixture of CuCl (15.0 mol%) and ligand 1 (20.0 mol%) in DMF (2.0 mL), aryl iodide (1.0 mmol), NaOH (2.0 mmol). The mixture was vigorously stirred at 120 C for 14 h under a dry nitrogen atmosphere. After completion of the reaction (as monitored by TLC), H2O was added and the organic layer was extracted with EtOAc, washed with brine and dried over MgSO4. The solution was filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography. The purity of the compounds was checked by 1H NMR and yields are based on aryl iodide. All the products are known and the spectroscopic data (FT-IR and NMR) and melting points were consistent with those reported in the literature.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 288-32-4, its application will become more common.

Reference:
Article; Sajadi, S. Mohammad; Maham, Mehdi; Journal of Chemical Research; vol. 38; 2; (2014); p. 128 – 129;,
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

Related Products of 53484-15-4,Some common heterocyclic compound, 53484-15-4, name is 5-Bromo-1-methyl-1H-benzo[d]Imidazole, molecular formula is C8H7BrN2, 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.

Into a 100-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of (S)-(4-(4-(tert-butoxycarbonyl)-3-methylpiperazine-l- carbonyl)-3-fluorophenyl)boronic acid (837 mg, 2.29 mmol, 1.00 equiv) in toluene (20 mL), 5-bromo-l-methyl- lH-l,3-benzodiazole (400 mg, 1.90 mmol, 0.83 equiv), Pd(PPh3)4 (264 mg, 0.23 mmol, 0.10 equiv), sodium carbonate(2M, 10 mL), ethanol (2.8 mL). The resulting mixture was stirred overnight at 95C. After cooled to room temperature, the resulting solution was diluted with 20 mL of H20, extracted with 3×30 mL of ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane/methanol (90: 10). The collected fractions were combined and concentrated under vacuum. This resulted in 800 mg (77%) of the title compound as a brown solid. LC-MS (ES, m/z) 453 [M+H]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-1-methyl-1H-benzo[d]Imidazole, its application will become more common.

Reference:
Patent; FORMA THERAPEUTICS, INC.; BAIR, Kenneth, W.; LANCIA, David, R.; LI, Hongbin; LOCH, James; LU, Wei; MARTIN, Matthew, W.; MILLAN, David, S.; SCHILLER, Shawn, E.r.; TEBBE, Mark, J.; WO2014/164749; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 14741-71-0,Some common heterocyclic compound, 14741-71-0, name is Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate, molecular formula is C11H12N2O2, 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: Et3N(4 mmol) was added dropwise to a stirred solution of the benzimidazole (1.5 mmol) and the dichloride compound 1(2 mmol) in CH2Cl2 (3 mL) at 0 C. The resulting mixture was stirred at room temperature overnight and worked up as for Method A.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate, its application will become more common.

Reference:
Article; Innes, Dylan; Perkins, Michael V.; Liepa, Andris J.; Francis, Craig L.; Australian Journal of Chemistry; vol. 71; 1; (2018); p. 58 – 69;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 52099-72-6, name is 1-(Prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one, 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 52099-72-6, HPLC of Formula: C10H10N2O

93.8 ml (150 mmol) of a n-butyllithium solution (about 1.6M in hexane) are added dropwise at 0-5 to 24.8 g (150 mmol) of 2-(N-benzyl-N-methylamino)ethanol dissolved in 250 ml of absolute tetrahydrofuran. After stirring at 0 for 15 minutes 11.7 ml (150 mmol) of methanesulphochloride in 50 ml of tetrahydrofuran are added dropwise at a temperature between 0 and 5 and the reaction mixture is stirred at 0 for 30 minutes. 5.8 g (133 mmol) of a 55% sodium hydride dispersion in mineral oil are washed oil-free with hexane and suspended in 40 ml of dimethylformamide. 23.1 g (132.5 mmol) of 1-(1-methylvinyl)benzimidazolin-2-one in 90 ml of dimethylformamide are subsequently added dropwise at room temperature and the reaction mixture is stirred for a further 15 minutes. This reaction mixture is added dropwise at 0 to the reaction solution described above. Thereafter, the mixture is heated to 70 and stirred for 3 hours. The reaction mixture is subsequently poured into 1 l of ice-water and extracted with 600 ml of methylene chloride. The extract is washed with water, dried over potassium carbonate and evaporated. The thus-obtained product is chromatographed on 500 g of silica gel with methylene chloride and 0-5% isopropanol as the elution agent, whereby there are obtained 26.8 g (63%) of 1-(1-methylvinyl)-3-[2-(N-benzyl-N-methylamino)ethyl]-2-benzimidazolinone as an oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(Prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one, and friends who are interested can also refer to it.

Reference:
Patent; Hoffmann-La Roche Inc.; US4808605; (1989); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1849-02-1, The chemical industry reduces the impact on the environment during synthesis 1849-02-1, name is 2-Chloro-1-methyl-1H-benzo[d]imidazole, I believe this compound will play a more active role in future production and life.

b. 1-methyl-2-(Piperazin-1-yl)-benzimidazole A mixture of 1 g (6.02 mmol) of 2-chloro-1-methyl-benzimidazole and 2.58 g (30 mmol) of piperazine is heated to 150C. without a solvent. The cooled melt is combined successively with water and dilute hydrochloric acid and extracted with dichloromethane. Then the aqueous phase is made alkaline with dilute sodium hydroxide solution and extracted with dichloromethane. The organic phase is dried over sodium sulphate and concentrated by evaporation. The product is purified by column chromatography on silica gel (eluant: dichloromethane/ethanol/ammonia=5:1:0.1). Yield: 0.4 g (30.8% of theory), Melting point: 99 C.

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-Chloro-1-methyl-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Lehmann-Lintz, Thorsten; Heckel, Armin; Thomas, Leo; Mark, Michael; US2003/166637; (2003); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1402838-08-7, 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. 1402838-08-7 name is 2-(1-Trityl-4-imidazolyl)benzaldehyde, 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.

To a three-necked flask was added 2- (1-trityl-1H-imidazole-4-) benzaldehyde (400 mg, 0.97 mmol)Acetylcyclohexane (122 mg, 0.97 mmol)And anhydrous tetrahydrofuran (5 ml)Under nitrogen protection,A solution of sodium ethoxide (85 mg, 1.25 mmol) in ethanol was added at room temperature,Stir at room temperature for 3 h, spin dry solvent,Saturated ammonium chloride (10 ml) was added,The organic layer was extracted with ethyl acetate and dried over anhydrous sodium sulfate. The solvent was dried, acetic acid (1 ml) and ethanol (5 ml) were added, stirred at 90 C for 3 h, cooled to room temperature, and saturated sodium carbonate was added to adjust pH = 10 , Extracted with ethyl acetate, the combined organic layers were dried over anhydrous sodium sulfate,Concentrated solvent,Purification by column chromatography on silica gel afforded compound 9 (210 mg, yield 77%

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(1-Trityl-4-imidazolyl)benzaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; Hinova Pharmaceuticals Inc.; Fan, Lei; Chen, Ke; Li, Xinghai; Chen, Yuanwei; (24 pag.)CN106256830; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 139481-44-0, 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 139481-44-0 as follows.

Example 9Ethyl 2-ethoxy-l -((2′-((hydroxyamino)iminomethyl)biphenyl-4-yl)methyl)-lH-benzo[c ]- imidazole-7-carboxylate (lb) – modification of the process (J Med. Chem. 1996, 39(26), 5228-5235)Triethylamine (3.4 ml = 2.48 g) was added to a suspension of hydroxylamine hydrochloride (1.7 g, 25 mmol) in DMSO (8 ml) and the mixture was stirred at the laboratory temperature for 15 minutes. The thick slurry was then aspirated and washed with tetrahydrofuran (10 ml). The filtrate was concentrated in vacuo (most tetrahydrofuran evaporated). The nitrile (IVa; 2.06 g, 5 mmol) was added to this solution and the mixture was stirred at the laboratory temperature for 15 minutes. Then, the mixture was partitioned into 4 reaction vials and these were stirred at the laboratory temperature (A), at the temperature of 50 C (B), 75 C (C) and 100 C (D) for 48 hours. Then the reaction mixtures were analyzed using HPLC.

According to the analysis of related databases, 139481-44-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ZENTIVA, K.S.; RADL, Stanislav; WO2012/119573; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 641571-11-1, These common heterocyclic compound, 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, 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.

To a solution of 15a (80 mg, 0.35 mmol) in NMP (2 mL) was added SOd2 (62 mg, 0.52 mmol). The reaction was heated at 90 C for 1 hour before 3 (84 mg, 0.35 mmol) was added. The resulting mixture was stirred at 90 C for 3 hours. The reactionwas quenched with water and basified with aqueous NaOH. The mixture was extracted with EtOAc twice. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The residue was purified by reverse prep-HPLC and then silica gel prep-TLC to give 4-methyl-N-(3-(4-methyl-1 H-imidazol-1 -yl)-5- (trifluoromethyl)phenyl)-3-(pyrimidin-2-ylamino)benzamide (12 mg, 7.6%) as a slightlyyellow 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

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 3314-30-5 as follows. Formula: C8H6N2O

General procedure: The equimolar aldehyde 3a?3d (1 mmol) and substituted phenylhydrazine 5a?5s (1 mmol) weremixed in CH3OH (10 mL) and stirred at room temperature [18]. After about 2 h, the reaction wascompleted (monitored by TLC). The residual crude was purified via silica gel column chromatogramusing a gradient mixture of petroleum ether and ethyl acetate to obtain the pure target compounds6a?6ai (in 45?80percent yield).

According to the analysis of related databases, 3314-30-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Xing; Chen, Yong-Fei; Yan, Wei; Cao, Ling-Ling; Ye, Yong-Hao; Molecules; vol. 21; 11; (2016);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem