Month: May 2021

Synthetic Route of 50790-93-7,Some common heterocyclic compound, 50790-93-7, name is 2-Butylimidazole, molecular formula is C7H12N2, 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.

(i) 4-Bromo-2-n-butylimidazole A solution of 20 g (0.16 mol) of 2-n-butylimidazole in 1.2 L of carbon tetrachloride was treated with 57.2 g (0.32 mol) of N-bromosuccinimde and heated with good stirring at 60 for 18 h. Then an additional 10 g of N-bromosuccinimide was added and the heating continued for 4 hours. The solids were collected by filtration. Evaporation of the filtrate gave 15 g of an oily solid which was mostly 2-n-butyl-4,5-dibromoimidazole. Evaporation of the solution obtained by trituration of the initial solids with methylene chloride and concentration gave additional product which was chromatographed over silica (20% ethyl acetate in hexane) to give, when combined with the first fraction, 34.2 g (76%) of dibromo product. A solution of 33.5 g (0.119 mol) of this product in 250 ml of n-propanol was refluxed for 18 hours with a suspension of 100 g (0.794 mol) of sodium sulfite. An additional 50 g of sodium sulfite was added and the mixture refluxed an additional 20 hours. The reaction mixture was concentrated under vacuum, 800 ml of water was added, and then the product was extracted into ether at pH 8. The ether layer was washed with water and brine, dried over sodium sulfate, and concentrated to give 23 g of a solid. Chromatography of the crude product (silica gel, 15-30% ethyl acetate-hexane) gave 7.51 g (31%) of pure 2-n-butyl-4-bromoimidazole.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Butylimidazole, its application will become more common.

Reference:
Patent; SmithKline Beecham Corporation; US5728842; (1998); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 29518-68-1, 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. 29518-68-1 name is 2-(1H-Benzo[d]imidazol-2-yl)ethanamine, 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.

General procedure: A suitable round bottom flask or reacti-vial was charged with aryl halide (1 equiv.), tryptamine (1.1 equiv.), IPA (lOmL/mmol) and triethylamine (2 equiv.) and heated at 100C for 3 h (reaction monitored by UPLC analysis). On cooling the reaction mixture was evaporated to dryness and the resultant residue partitioned between ethyl acetate and water. The organic phase was separated and sequentially washed with saturated bicarbonate solution, water, brine, then dried over sodium sulfate, filtered and evaporated. Purification, if required was performed by chromatography or trituration.

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

Reference:
Patent; JAGUAHR THERAPEUTICS PTE LTD; METE, Antonio; HITCHIN, James, R,; GRAHAM, Mark; KING-UNDERWOOD, John; THORNE, Philip, Vellacott,; (62 pag.)WO2020/39093; (2020); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

70631-93-5, name is 5-Methyl-1H-imidazole-2-carboxylic acid, 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. name: 5-Methyl-1H-imidazole-2-carboxylic acid

A mixture of N-cyclopropyl-8-((4-methoxybenzyl)(methyl)amino)-6-((2-oxo- 1- (piperidin-4-yl)- 1 ,2-dihydropyridin-3 -yl)amino)imidazo[ 1 ,2-b]pyridazine-3-carboxamide(0.0 15 g, 0.028 mmol), 4-methyl-1H-imidazole-2-carboxylic acid (6.97 mg, 0.055 mmol), BOP (0.024 g, 0.055 mmol) and N,N-Di-iso-propylethylamine (0.018 g, 0.138 mmol) in DMF (1.0 mL) was stirred at room temperature overnight. The reaction mixture was concentrated. The residue was dissolved in 2m1 dichloromethane. 0.2 ml TFA was added and the reaction mixture stirred at room temperature overnight. The crude productmixture was chromatographed using Reverse-Phase PREP LC to give N-cyclopropyl-6- ((1 -(1 -(4-methyl- 1H-imidazole-2-carbonyl)piperidin-4-yl)-2-oxo- 1 ,2-dihydropyridin-3- yl)amino)-8-(methylamino)imidazo [1 ,2-b]pyridazine-3 -carboxamide (0.007g, 0.014 mmol, 50% yield) as a white solid.

The synthetic route of 70631-93-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LIU, Chunjian; LIN, James; MOSLIN, Ryan M.; WEINSTEIN, David S.; TOKARSKI, John S.; WO2015/89143; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 914306-50-6,Some common heterocyclic compound, 914306-50-6, name is 1-(2,6-Diisopropylphenyl)-2-phenyl-1H-imidazole, molecular formula is C21H24N2, 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.

In a 500 ml round bottom flask flushed with argon were introducedIrCl3.xH20 (6.48 g, 18.3 mmol) and l-(2,6-diisopropylphenyl)-2-phenyl-lH- imidazole ligand (16.74 g, 55 mmol) followed by addition of 356 ml of a 3: 1 (v/v) mixture of 2-ethoxy-ethanol and water. The resulting mixture was outgassed and heated under stirring at reflux for 21h. After cooling, the precipitate was filtered off with suction, washed with methanol and dried under vacuum. The reaction yield was 84 %.2nd step: preparation of a fac-isomer of the metal complex of formula (IV)A fac-isomer of the metal complex of formula (IV) was obtained in an identical manner to Example 1 except that l-(2,6-diisopropylphenyl)-2-phenyl- lH-imidazole was used as ligand instead of l-(2,6-dimethylphenyl)-2-phenyl- lH-imidazole. The fac-isomer yield estimated, as in example 1, from NMR analysis of the recovered precipitate is equal to 85 %; no mer-isomer was detected.

The synthetic route of 914306-50-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SOLVAY SA; VAN PEE, Veronique; CATINAT, Jean-Pierre; WO2012/84219; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

326-55-6, name is 6-(Trifluoromethyl)-1H-benzo[d]imidazole, 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. Application In Synthesis of 6-(Trifluoromethyl)-1H-benzo[d]imidazole

Add 0.3mmol 5-trifluoromethylbenzimidazole, 0.009mmol photosensitizer, 0.6m mol sodium hydroxide to a 15ml schlenck tube,After the nitrogen protection was completed, 0.6 mmol of ethyl bromodifluoroacetate and 3 mL of DMF were added with a syringe.Then, it reacted at room temperature for 12 hours under 15 W blue light irradiation.After the reaction, add two medicine spoon column chromatography silica gel (100-200 mesh) to the reaction solution, and remove the solvent by distillation under reduced pressure.The product was purified by column chromatography (petroleum ether / ethyl acetate = 50: 1 as eluent). The material was a yellow liquid with a yield of 73%.

The synthetic route of 326-55-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang University of Technology; Liu Yunkui; Hu Xiaojun; Zhou Bingwei; (10 pag.)CN110483406; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 68468-39-3, 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. 68468-39-3, name is 5-Bromo-1H-benzo[d]imidazole-2(3H)-thione belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Description 19: S-Bromo-lH-benzoimidazole^-sulfonic acid; [00281] Thiocarbonyl diimidazole (0.95 g, 5.35 mmol) was added in one portion to a solution of 4-bromobenzene-l,2-diamine (1.00 g, 2.67 mmol) in TetaF (50 mL). The mixture was stirred for 6 h then the solvents were removed in vacuo. The residue was suspended in DCM and the product was collected by filtration as a white solid. This was dissolved in KOeta solution (IM, 10.7 mL, 10.7 mmol) and eta2O2 (30 %, 2.13 mL, 21.40 mmol) was added dropwise. The mixture was stirred for 14 h then concentrated HCl was added to pH 1. The mixture was cooled to 0 0C for 30 min then the white solid product was collected by filtration. This was dried at 40 0C under high vacuum (1.15 g, 77 %). MS (MH+, m/z) 275 (50 %), 277 (50 %).

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, 5-Bromo-1H-benzo[d]imidazole-2(3H)-thione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GALAPAGOS N.V.; WO2008/55959; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 67768-61-0, name is 1-Cyclohexyl-1H-imidazole, 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 67768-61-0, HPLC of Formula: C9H14N2

D) 1,1′-Dicyclohexyl-3,3′-methylenediimidazolium diiodide 11 0.0065 mol of diiodomethane (1.741 g; 0.52 ml) and 5 ml of tetrahydrofuran are added to 0.013 mol of cyclohexylimidazole (2.000 g) in an ACE pressure tube. The reaction mixture is stirred at 80 C. for 3 hours. The solid which precipitates is washed repeatedly with a little tetrahydrofuran. The white solid 11 is obtained. Empirical formula: C19H30N4I2 M=568.270 g/mol Yield: 0.891 g (24.1% of theory) Melting point: decomposition at >286 C. 1H (ppm, d6-DMSO, 300.13 MHz): delta=9.45 (s, 2H, NCN); 8.01 (dd, 4H, J=1.6 Hz, NCCN); 6.58 (s, 2H, NC2N); 4.36 (t, 2H, J=11.7 Hz, C of cyclohexyl ring); 2.09 (d, 4H, J=9.7 Hz, C2 of cyclohexyl ring); 1.85 (d, 4H, J=13.3 Hz, C2 of cyclohexyl ring); 1.68 (d, 4H, J=12.3 Hz, C2 of cyclohexyl ring); 1.40 (quart, 4H, J=12.7 Hz, C2 of cyclohexyl ring); 1.23 (t, 4H, J=12.5 Hz, C2 of cyclohexyl ring)

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

Reference:
Patent; BASF SE; TECHNISCHE UNIVERSITAET DRESDEN; US2009/326237; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 65039-05-6, name is 1-Butyl-3-methylimidazolium iodide, 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 65039-05-6, Product Details of 65039-05-6

General procedure: 2.0mmol,0.5825gCo(NO3)2 6H2O and0.50mmol,0.0831gH2BDC wereplacedinacrystallisationvialplacedina25mLteflon-lined stainless-steelautoclavemixedwith1.005g[EMI]Cl.Themixturewaskeptinsidethe furnaceat160 C for5days,andthennaturallycooledtoambient temperature.Thebluecrystalsof 1 suitable forsinglecrystalX-raydiffractionwerecollectedaftersoakclearingwithacetone.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Butyl-3-methylimidazolium iodide, and friends who are interested can also refer to it.

Reference:
Article; Zhang, Zong-Hui; Xu, Ling; Jiao, Huan; Journal of Solid State Chemistry; vol. 238; (2016); p. 217 – 222;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 88704-72-7, A common heterocyclic compound, 88704-72-7, name is 2-(1H-Benzo[d]imidazol-2-yl)ethanamine hydrochloride, molecular formula is C9H12ClN3, 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: To compound 5, 6 or 7 (1 equiv) and the appropriate alkylamine(1.3 equiv) in anhydrous DMF (10 mL/mmol) were added DIEA (3equiv) and PyBOP (1 equiv), and the reaction mixturewas stirred atroom temperature under argon. When the reaction was complete(2 h – 4 h), the solvents were removed under reduced pressure togive a residue that was taken up in CH2Cl2. The solution waswashed with saturated aqueous NaHCO3, then water. The organiclayer was dried over Na2SO4 and then evaporated in vacuo. Purificationby flash chromatography afforded the corresponding amidederivatives 8, 9 or 10 (yield: 40-76%).

The synthetic route of 88704-72-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Paoletti, Julie; Assairi, Liliane; Gelin, Muriel; Huteau, Valerie; Nahori, Marie-Anne; Dussurget, Olivier; Labesse, Gilles; Pochet, Sylvie; European Journal of Medicinal Chemistry; vol. 124; (2016); p. 1041 – 1056;,
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 106848-38-8 as follows. Application In Synthesis of 1-Benzyl-4-bromo-1H-imidazole

General procedure: PdCl2(dppf), PdCl2(tbpf) and (A.caPhos)PdCl2. A mixture of the halogenated heterocycle (0.66 mmol) in anhydrous THF (13.2 mL) was degassed by bubbling argon for few minutes. Then, PdCl2(dppf) (27.0 mg, 0.033 mmol, 5.0 mol%), TMEDA (0.130 g, 1.12 mmol, 1.7 equiv) and finally NaBH4 (42.4 mg, 1.12 mmol, 1.7 equiv) were introduced in sequence. The mixture was stirred at room temperature under argon for the proper time and then worked up as described above.

According to the analysis of related databases, 106848-38-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Chelucci, Giorgio; Figus, Susanna; Journal of Molecular Catalysis A: Chemical; vol. 393; (2014); p. 191 – 209;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem