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. COA of Formula: C15H13N3S
A pressure vessel containing the compound of Formula (5) (10 g, 37.40 mmol) and methyl 3-bromopropionate (7.73 g, 44.88 mmol) in N,N-dimethylformamide (70 mL) was sealed and heated to an external temperature of 60 C. for 3 days. The reaction was then cooled to room temperature to allow for a sample of the reaction mixture to be taken for 1H-NMR analysis (91% conversion). Methyl 3-bromopropionate (97%, 1.25 g, 7.48 mmol) was charged to the vessel and the reaction was re-sealed and heated to an external temperature of 60 C. for 24 hours. Following completion of the reaction, the reaction solution was concentrated in vacuo at 35-40 C. to remove the N,N-dimethylformamide. The resulting oil residue was then dissolved in dichloromethane (100 mL) and washed with a saturated aqueous sodium bicarbonate solution (50 mL), with the organic phase being dried over anhydrous sodium sulfate and concentrated in vacuo at 30-35 C. to afford a green oil (17.07 g). The oil was purified by silica gel column chromatography (column 27 cm*6 cm), using a gradient system of ethyl acetate and heptanes (2 L, 40:60 ethyl acetate:heptanes; 1 L, 50:50 ethyl acetate:heptanes; 2 L, ethyl acetate) to afford the compound of Formula (11) (9.75 g; 67% yield from the compound of Formula (5)) as a dark oil. 1H-NMR (CDCl3, 300 MHz) delta: 0.78-0.93 (2H, m), 1.12-1.21 (2H, m), 2.42 (1H, tt, J=5.44 Hz, 8.46 Hz), 2.91 (2H, t, J=6.77 Hz), 3.47 (2H, t, J=6.86 Hz), 3.64 (3H, s), 7.30 (1H, d, J=8.25 Hz), 7.35 (2H, s), 7.57 (1H, apparent dt, J=1.02 Hz, 8.22 Hz), 7.66 (1H, apparent dt, J=1.02 Hz, 8.04 Hz), 8.30 (1H, s), 8.54 (1H, d, J=8.44 Hz).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1533519-84-4, 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;,
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