Some common heterocyclic compound, 17641-08-6, name is 2-Chloro-N-(3-methoxyphenyl)acetamide, molecular formula is C9H10ClNO2, 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. Safety of 2-Chloro-N-(3-methoxyphenyl)acetamide
General procedure: A mixture of the potassium salt 22 (1.5g, 0.01mol) and the appropriate chloroacetanilides (0.01mol) namely, 2-chloro-N-(3-methoxyphenyl)acetamide and 2-chloro-N- (4-fluorophenyl)acetamide in dry DMF (20ml) was heated over a water bath for 3h. The reaction mixture was then cooled, poured into ice-cooled water (150ml) and stirred well for 30min. The solid such separated was filtered, washed with water, dried and crystallized from methanol/toluene mixture (1:1) to afford the corresponding compounds 25a – b, respectively. 2-(Bis[1,2,4]triazolo[4,3-a:3?,4?-c]quinoxalin-3-ylsulfanyl)-N-(3-methoxyphenyl) acetamide (25a). White crystal (yield 71 %); m. p. 256 – 259 C; IR (KBr, cm1); 3264 (NH), 3077 (CH aromatic), 2950 (CH aliphatic), 1689 (C=O amide); 1H NMR (DMSO-d6) delta ppm: 3.70 (s, 3H, -OCH3), 4.52 (s, 2H, CH2), 6.62 (d, 1H, J=8.1Hz, Ar-H, H-4 of phenyl), 6.69 (d, 1H, J=8.4Hz, Ar-H, H-6 of phenyl), 7.20 (dd, 1H, J=8.1, 8.4Hz, Ar-H, H-5 of phenyl), 7.23 (s, 1H, Ar-H, H-2 of phenyl), 7.72 (dd, 1H, J=7.8, 8.4Hz, Ar-H, H-7 of quinoxaline), 7.74 (dd, 1H, J=7.8, 8.1Hz, Ar-H, H-6 of quinoxaline), 8.45 (d, 1H, J=8.4Hz, Ar-H, H-8 of quinoxaline), 8.59 (d, 1H, J=8.1Hz, Ar-H, H-5 of quinoxaline), 10.02 (s, 1H, Ar-H, N-CH=N), 10.54 (s, 1H, -NH, D2O exchangeable); 13C NMR (DMSO-d6, 100 MHz) delta (ppm): 38.9, 55.4, 105.4, 109.4, 111.8, 118.0, 118.5, 123.1, 124.0, 128.3 (2), 130.0, 138.7, 139.4, 140.3, 142.3, 147.7, 159.9, 165.5; DEPT (DMSO-d6, 100 MHz) delta (ppm): 38.9 (1CH3), 55.4 (1CH2), 105.3, 109.4, 111.8, 118.0, 118.5, 128.3 (2), 130.0, 138.7 (9CH); Anal. Calcd. for C19H15N7O2S (405.43): C, 56.29; H, 3.73; N, 24.18. Found: C, 56.42; H, 3.71; N, 24.39 %.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 17641-08-6, its application will become more common.
Reference:
Article; Ibrahim; Taghour; Metwaly; Belal; Mehany; Elhendawy; Radwan; Yassin; El-Deeb; Hafez; ElSohly; Eissa; European Journal of Medicinal Chemistry; vol. 155; (2018); p. 117 – 134;,
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