Application of 645-36-3,Some common heterocyclic compound, 645-36-3, name is 2,2-Diethoxyethanamine, molecular formula is C6H15NO2, 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.
A solution of 1,4-dimethyl-3-formylcarbazole (500 mg, 2.2 mmol) in benzene (15 mL) and 2,2-diethoxyethylamine (330 mg, 2.5mmol) was placed in a flask. The mixture was refluxed for 2 h. After the reaction, the solvent was evaporated under the reduced pressure. MeOH (15 mL) was added to the residue. NaBH4 (800 mg, 22mmol) was then added slowly, and the reaction mixture was stirred at rt for 2 h. The solvent was evaporated under the reduced pressure. The residue was extracted with CHCl3 and dried over Na2SO4, andconcentrated under reduced pressure. A solution of the residue in a mixture of MeCN (10 mL) andpyridine (1 mL) was placed in a flask. After the solution was stirred at rt for 0.5 h, 2-nitrobenzenesulfonylchloride (1.0 g, 4.5 mmol) was added, and the reaction mixture was stirred at rt for 24 h. After thereaction, the solvent was evaporated under reduced pressure. The crude product was recrystallized from MeOH, affording N-(2,2-diethoxyethyl)-N-((1,4-dimethyl-9H-carbazol-3-yl)methyl)-2-nitrobenzenesulfonamide (85%, 1.0 g); yellow solid; mp 175.0-176.0 C; 1H NMR (500 MHz, CDCl3) delta 1.46 (6H, t, J= 7 Hz), 2.41 (3H, s), 2.73 (3H, s), 3.41-3.46 (4H, m), 3.61-3.64 (2H, m), 4.56 (1H, t, J = 5.5 Hz), 4.88(2H, s), 7.07 (1H, s), 7.21-7.26 (1H, m), 7.36-7.42 (2H, m), 7.47 (1H, d, J = 8 Hz), 7.52 (1H, d, J = 8 Hz),7.60 (1H, d, J = 8 Hz), 7.77 (1H, d, J = 8 Hz), 8.03 (1H, brs), 8.15 (1H, d, J = 8 Hz); 13C NMR (CDCl3,125 MHz) delta 15.3, 15.9, 16.5, 49.6, 50.6, 63.4, 102.2, 110.6, 116.8, 119.5, 121.9, 122.8, 123.7, 123.8,124.3, 125.1, 128.7, 130.4, 130.8, 131.1, 132.8, 134.4, 138.4, 139.6, 147.8; MS (FAB+) m/z 525 [M+];HRMS (FAB+): calcd for C27H31N3O6S (M+) 525.1933, found 525.1921.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,2-Diethoxyethanamine, its application will become more common.
Reference:
Article; Sato, Naoya; Kawai, Yu; Akaba, Yosuke; Honma, Shoji; Sakai, Norio; Konakahara, Takeo; Heterocycles; vol. 92; 4; (2016); p. 664 – 679;,
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