Extended knowledge of 1533519-84-4

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Application of 1533519-84-4, New Advances in Chemical Research in 2021. Chemo-enzymatic cascade processes are invaluable due to their ability to rapidly construct high-value products from available feedstock chemicals in a one-pot relay manner. 1533519-84-4, name is 4-(4-Cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione, molecular formula is C15H13N3S, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, 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).

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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,
Triazoles – an overview | ScienceDirect Topics