Application of 2576-47-8, A common heterocyclic compound, 2576-47-8, name is 2-Bromoethylamine hydrobromide, molecular formula is C2H7Br2N, 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.
A solution of 2-bromoethylamine hydrobromide (1.1 g, 5.4 mmol) and aniline (3.0 g, 32 mmol) in toluene (8 ml) was stirred for 1 day at 120 C under an argon atmosphere and the precipitated product was collected by filtration. The salt was then treated with a 20% aqueous NaOH solution and extracted with dichloromethane. The organic phase was dried over anhydrous Na2SO4. After the Na2SO4 was filtered out and the solvent was distilled the crude product was further purified by column chromatography on silica gel (eluant: methanol) to afford N-phenylethylenediamine as a red-brown liquid. Yield: 87% (0.64 g); 1H NMR (400 MHz, CDCl3) delta 1.51 (br s, 3H), 2.93 (t, 2H), 3.17 (t, 2H), 6.63 (d, 2H), 6.70 (t, 1H), 7.17 (t, 2H). 2-(Chloromethyl)pyridine hydrochloride (1.8 g, 11 mmol) was treated with a 20% aqueous NaOH solution and extracted with dichloromethane and the organic phase was dried over anhydrous Na2SO4. After Na2SO4 was filtered out and the solvent was evaporated off, a solution of 2-(chloromethyl)pyridine in benzene (3 ml) was added to a solution of N-phenylethylenediamine (0.69 g, 5.1 mmol), which was prepared as described above, and triethylamine (5.1 g, 51 mmol) in benzene (4 ml) and stirred for 17 h at 80 C under an argon atmosphere. After being cooled to room temperature and the addition of diethyl ether, the inorganic by-products were removed by washing with a saturated NaHCO3 solution and with brine. The organic phase was dried over anhydrous Na2SO4. After the Na2SO4 was filtered out and the solvent was removed the crude product was purified by column chromatography on silica gel (eluant: ethyl acetate) to afford 2a as a red-brown viscous liquid. Yield: 69% (1.1 g);
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Article; Maruyama, Takayuki; Fujie, Yasuyuki; Oya, Noriyuki; Hosaka, Eisuke; Kanazawa, Aki; Tanaka, Daisuke; Hattori, Yoshiyuki; Motoyoshiya, Jiro; Tetrahedron; vol. 67; 36; (2011); p. 6927 – 6933;,
Bromide – Wikipedia,
bromide – Wiktionary