Electric Literature of 1533519-84-4,Some common heterocyclic compound, 1533519-84-4, name is 4-(4-Cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione, molecular formula is C15H13N3S, 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.
To a solution of the compound of Formula (5) (30 g, 112.22 mmol) in N,N-dimethylformamide (94 mL) was charged sodium bicarbonate (18.39 g, 218.96 mmol) to provide a suspension. 1,2-Bis(chloroacetoxy)ethane (compound of Formula (4-A)) (11.77 g, 54.74 mmol) was then charged and the mixture stirred at room temperature for 72 hours. Following the completion of the reaction, the reaction mixture was poured into ice water (250 mL) over 10 minutes to form a slurry, which was warmed to room temperature and stirred for 1 hour. The product was then collected by filtration, washed with cold (0-5 C.) water (2*60 mL), and suction dried for 45 minutes to provide a damp cake. A new flask was charged with the damp cake along with dichloromethane (300 mL) and stirred at room temperature for 30 minutes to afford a clear, biphasic solution. The organic phase was removed and washed with water (2*120 mL), dried over anhydrous sodium sulfate, and concentrated in vacuo at 30-35 C. The foamy solid was then dried in vacuo at room temperature for 24 hours to afford the compound of Formula (3-A) as a foamy light yellow solid (quantitative yield, HPLC purity=99.35 area %). 1H-NMR (CDCl3, 300 MHz) delta: 0.75-0.94 (4H, m), 1.10-1.22 (4H, m), 2.41 (2H, tt, J=5.64 Hz, 8.47 Hz), 4.08 (ABq, 4H, DeltadeltaAB=0.05, JAB=16.36 Hz), 4.34 (4H, s), 7.29-7.43 (6H, m), 7.57 (2H, apparent dt, J=1.23 Hz, 7.64 Hz), 7.66 (2H, apparent dt, J=1.23 Hz, 7.60 Hz), 8.28 (2H, s), 8.53 (2H, d, J=8.35 Hz).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(4-Cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione, its application will become more common.
Reference:
Patent; Apotex Inc.; Bodhuri, Prabhudas; Green, Melanie R. A.; Karadeolian, Avedis; Weeratunga, Gamini; Gorin, Boris; (33 pag.)US2018/258057; (2018); A1;,
1,2,3-Triazole – Wikipedia,
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