Application of 195053-92-0, The chemical industry reduces the impact on the environment during synthesis 195053-92-0, name is 2-(1-Trityl-1H-imidazol-4-yl)ethanamine, I believe this compound will play a more active role in future production and life.
A mixture of Meldrum’s acid (5.52 g, 38.3 mmol), potassium carbonate (26.5 g, 191 mmol) and methyl iodide (7.15 mL, 115 mmol) in acetonitrile (75 mL) was heated at 75 C in a sealed tube for 7 hrs. The mixture was cooled to room temperature, diluted with dichloromethane (300 mL), filtered and the filtrate evaporated to dryness in vacuo. Ethyl acetate (75 mL), hexanes (75 mL) and water (50 mL) were added and phases were separated. The organic layer was washed with 10% aqueous solution of sodium thiosulfate (50 mL) and water (50 mL); dried over anhydrous magnesium sulfate and solvent removed in vacuo to give 2,2,5,5-tetramethyl-[1,3]dioxane-4,6-dione as white solid. Yield: 6.59 g (79%). RF (SiO2, chloroform/ethyl acetate, 98:2): 0.60. 1H NMR spectrum (300 MHz, CDCl3, deltaH): 1.76 (s, 6 H); 1.65 (s, 6 H). A solution of 2-(1-Trityl-1H-imidazol-4-yl)-ethyl amine (5.00 g, 14.2 mmol) prepared as described above and triethylamine (9.86 mL, 70.7 mmol) in toluene (80 mL) was added dropwise over 50 min to a solution of the above dione compound (3.65 g, 21.2 mmol) in toluene (40 mL) at 75 C. The mixture was stirred at this temperature for additional 3 hrs (until the starting amine was detected on TLC), then it was evaporated to dryness. The residue was redissolved in chloroform (300 mL) and washed with 10% aqueous solution of citric acid (200 mL). The aqueous phase was extracted with chloroform (2 x 60 mL); the chloroform phases were combined, dried over anhydrous magnesium sulfate and solvent removed in vacuo. The residue was triturated with hot chloroform (140 mL); hexanes (70 mL) were added and the suspension was stirred at room temperature overnight. Solids were filtered off, washed with chloroform/hexanes mixture (1:1, 2 x 50 mL) and dried in vacuo to give the title product. Yield: 6.73 g (88%). M.p.: 161-162 C. RF (SiO2, chloroform/methanol, 85:15): 0.40. 1H NMR spectrum (300 MHz, DMSO-d6, deltaH): 12.45 (bs, 1 H); 7.66 (t, J=5.1 Hz, 1 H); 7.57-7.31 (m, 9 H); 7.26 (s, 1 H); 7.20-7.02 (m, 6 H); 6.66 (s, 1 H); 3.25 (m, 2 H); 2.57 (t, J=7.3 Hz, 2 H); 1.21 (s, 6 H).
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-(1-Trityl-1H-imidazol-4-yl)ethanamine, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; Novo Nordisk A/S; SAUERBERG, Per; LAU, Jesper; LINDEROTH, Lars; KODRA, Janos Tibor; SPETZLER, Jane; GARIBAY, Patrick William; (119 pag.)EP3000482; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem