1953-99-7, A common heterocyclic compound, 1953-99-7, name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, molecular formula is C8Cl4N2, 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.
Compound 3 was synthesized according to the reported procedure[27]. To the solution of tetrachlorophthalonitrile (1) (2 g,7.5 mmol) in anhydrous DMF (15 ml), 3-(diethylamino)phenol (2)(1.24 g, 7.5 mmol) was added. The reaction was allowed to stir for15 min, and finely powdered anhydrous Na2CO3 (1.59 g, 15 mmol)was added in portions to the reaction mixture over 1 h with efficientstirring. Then, the mixture was stirred at 30 C for 3 h. After3 h, the reaction was cooled to room temperature, poured into icecoldwater, extracted with ethyl acetate, washed with 1 M NaOHandwashed with a brine solution. The organic layerwas dried usingNa2SO4, and the solvents were evaporated to obtain the crudeproduct. The crude product was purified by column chromatographyusing hexane-ethyl acetate (90:10) as eluent. Yield (1.9 g65percent), 1H NMR (CDCl3, 300 MHz) d, 6.99 (t, J 8.4 Hz, 1H), 6.38 (dd,J 8.4 & 2.1 Hz, 1H), 6.22 (t, J 2.1 Hz, 1H), 5.68 (dd, J 7.8 & 1.5 Hz,1H), 3.26 (q, J 6.9 Hz, 4H) 1.10 (t, J 2.1 Hz, 6H) (Fig. S1), 13C NMR(CDCl3, 75 MHz) 155.9, 152.8, 148.6, 136.2, 135.3, 132.1, 129.2, 115.7,113.6, 110.8, 106.7, 99.1, 98.03, 43.4, 11.4 (Fig. S2). FT-IR (KBr pellet)(g, cm1) 2980 (AreCeH) 2920e2880 (Aliphatic-C-H), 2235 (C^N),1280 (CeOeC) (Fig. S3). LC-MS: m/z 396 [M2] (Fig. S4).
The synthetic route of 1953-99-7 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Muthukumar, Palanisamy; Kim, Hak-Soo; Jeong, Jong Woo; Son, Young-A.; Journal of Molecular Structure; vol. 1119; (2016); p. 325 – 331;,
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