Category: 13739-48-5

Adding a certain compound to certain chemical reactions, such as: 13739-48-5, name is 2-Methyl-4-phenyl-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 13739-48-5, Computed Properties of C10H10N2

5.86 3-{4-[4-(2-METHYL-4-PHENYL-IMIDAZOL-1-YLMETHYL)-BENZYLOXY]-1-OXO-1,3-DIHYDRO-ISOINDOL-2-YL}-PIPERIDINE-2,6-DIONE To the stirred solution of 2-methyl-4-phenyl-1H-imidazole (157 mg, 0.99 mmol) in Acetonitrile (15 mL) was added 3-(4-(4-(bromomethyl)benzyloxy)-1-oxoisoindolin-2-yl)piperidine-2,6-dione (400 mg, 0.9 mmol) and DIPEA (0.24 ml, 1.35 mmol) at room temperature. The reaction mixture was stirred at room temperature for 4 days before the reaction mixture was diluted by EtOAc (40 mL) and NaHCO3 (aq, sat., 20 mL). The mixture was extracted. Some solid was formed and the mixture was filtered. And the solid was dissolved in DCM (20 mL) and MeOH (5 mL). All organic layers were combined and dried by MgSO4 and concentrated. The residue was purified by ISCO to give 3-{4-[4-(2-Methyl-4-phenyl-imidazol-1-ylmethyl)-benzyloxy]-1-oxo-1,3-dihydro-isoindol-2-yl}-piperidine-2,6-dione as a white solid (310 mg, 66% yield). HPLC: Waters Symmetry C-18, 3.9*150 mm, 5 mum, 1 mL/min, 240 nm, 25/75, (CH3CN/0.1% H3PO4), 5.26 min (99.6%); mp: 270-272 C.; 1H NMR (DMSO-d6) delta 1.91-2.03 (m, 1H, CHH), 2.30 (s, 3H, CH3), 2.43 (dd, J=4.3, 13.0 Hz, 1H, CHH), 2.53-2.63 (m, 1H, CHH), 2.82-2.97 (m, 1H, CHH), 4.23 (d, J=17.6 Hz, 1H, CHH), 4.39 (d, J=17.6 Hz, 1H, CHH), 5.04-5.16 (m, 1H, CHH), 5.18 (s, 2H, CH2), 5.23 (s, 2H, CH2), 7.10-7.20 (m, 1H, Ar), 7.20-7.26 (m, J=8.1 Hz, 2H, Ar), 7.26-7.36 (m, 4H, Ar), 7.42-7.54 (m, 314, Ar), 7.62 (s, 1H, NH), 7.64-7.75 (m, 2H, Ar), 10.96 (s, 1H, NH); 13C NMR (DMSO-d6) delta 12.76, 22.31, 31.16, 45.04, 48.59, 51.55, 69.17, 114.93, 115.25, 116.49, 123.92, 125.88, 127.15, 128.14, 128.36, 129.78, 129.95, 133.30, 134.58, 135.98, 137.15, 138.50, 144.57, 153.39, 167.97, 170.93, 172.80; LCMS MH=521; Anal. Calcd for C31H28N4O4+0.3 H2O: C, 70.79; H, 5.48; N, 10.65; Found: C, 70.68; H, 5.21; N, 10.52. The regio isomeric structure was confirmed by ROESY.

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Reference:
Patent; Man, Hon-Wah; Muller, George W.; Ruchelman, Alexander L.; Khalil, Ehab M.; Chen, Roger Shen-Chu; Zhang, Weihong; US2011/196150; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 13739-48-5, 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. 13739-48-5, name is 2-Methyl-4-phenyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows.

Charged, imidazole (V) (2.529 m. moles), cesium carbonate (3.54 m. moles), cuprous oxide (0.152 m. moles), PEG (2.549 m. moles), 5-bromo-thiophen-2- carboxylic acid amide (1.947 m. moles), 4,7-dimethoxy-l,10-phenanthrolein (0.354 m. moles) to the DMSO (50 ml) in RB flask, and the reaction mixture was heated to 115-1200C and the temperature was maintained for 20 hrs. (Reaction is monitored by TLC). After completion of reaction, cooled to RT, diluted with DCM (250 ml) and filtered on hyflo bed. DCM was evaporated under reduced pressure. To the residue ammonia solution was added and extracted with ethyl acetate (250 ml X 3 times), which was then washed with water and dried over sodium sulfate. Ethyl acetate was evaporated under reduced pressure to get the crude product, which was purified by silica gel column chromatography using DCM: methanol 100 – 5% to get the desired compound (89) in 25 % yield.

The chemical industry reduces the impact on the environment during synthesis 2-Methyl-4-phenyl-1H-imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MASSACHUSETTS INSTITUTE OF TECHNOLOGY; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; GENZYME CORPORATION; WO2009/137081; (2009); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem