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. HPLC of Formula: C9H10ClNO2
General procedure: A mixture of 2-chloro-N-(4-chlorobenzyl)acetamide 3a (0.22 g, 1.0 mmol), 4-hydroxy-N-phenethyl-benzenesulfonamide 7a (0.42 g, 1.5 mmol), K2CO3 (0.21 g, 1.5 mmol) and KI (33 mg, 0.2 mmol) in acetone (20 ml) was stirred at 60 C for 7.0 h. After the organic solvent was evaporated, the residual was diluted with water (20 ml), extracted with dichloromethane, washed with brine and then dried over Na2SO4. After filtration and condensation, the crude product was obtained and recrystallized in ethyl acetate/hexane (1:1, v: v) to afford 1a as white solid (0.19 g, yield 42%). SAPA 1v was prepared by the reaction of 2-chloro-N-(3-methoxyphenyl)acetamide 3q with 7a according to the procedure described for SAPA 1a. Yield 46%; mp 107.0-108.0 C. ESI-MS m/z 441.3 (M+H)+. HRMS (ESI) of C23H24N2O5S (M+H)+ calcd, 441.1479; found, 441.1479. 1H NMR (400 MHz, DMSO-d6) delta 10.13 (s, 1H), 7.71 (d, J = 8.7 Hz, 2H), 7.57 (s, 1H), 7.30 (s, 1H), 7.28-7.10 (m, 9H), 6.65 (d, J = 7.9 Hz, 1H), 4.79 (s, 2H), 3.70 (s, 3H), 2.91 (s, 2H), 2.65 (t, J = 7.5 Hz, 2H). 13C NMR (151 MHz, DMSO-d6) delta 166.4, 161.1, 160.0, 140.0, 139.2, 133.2, 130.1, 129.1, 128.8, 126.7, 115.5, 112.4, 109.7, 105.9, 67.5, 55.5, 44.6, 35.7. HPLC purity: tR = 8.100, 98.9%.
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; Li, Ya-Li; Qi, Xiang-Yu; Jiang, Hui; Deng, Xiao-Dong; Dong, Yan-Ping; Ding, Ting-Bo; Zhou, Lu; Men, Peng; Chu, Yong; Wang, Ren-Xiao; Jiang, Xian-Cheng; Ye, De-Yong; Bioorganic and Medicinal Chemistry; vol. 23; 18; (2015); p. 6173 – 6184;,
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