Some common heterocyclic compound, 59681-66-2, name is 4-Chloro-N1-methylbenzene-1,2-diamine, molecular formula is C7H9ClN2, 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. Product Details of 59681-66-2
General procedure: A solution of compound 5 (R1=H, 100mg, 0.657mmol), 1,3-bis(tert-butoxycarbonyl)-2-methyl-2-thiopseudourea 6 (209mg, 0.722mmol), and p-toluene sulfonic acid (12mg, 0.065mmol) in isopropanol was heated at 65C for 16h. The reaction mixture was concentrated in vacuo and diluted with ethyl acetate. The organic layer was successively washed with 1N sodium hydroxide and brine, and dried over sodium sulfate. After concentration in vacuo, the crude product was purified by silica gel column chromatography (eluent : n-Hex/EA=5 : 1) to give the compound 7 (R1=H, 121mg, yield 75%) as solid. 1H NMR (400MHz, DMSO-d6) delta 11.9 (NH, 1H), 7.38 (m, 2H), 7.14 (m, 2H), 3.65 (s, 3H), 1.45 (s, 9H); LC/MS (electrospray) m/z (M+H)+ 248.03.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 59681-66-2, its application will become more common.
Reference:
Article; Windisch, Marc Peter; Jo, Suyeon; Kim, Hee-Young; Kim, Soo-Hyun; Kim, Keumhyun; Kong, Sunju; Jeong, Hyangsuk; Ahn, Sujin; No, Zaesung; Hwang, Jong Yeon; European Journal of Medicinal Chemistry; vol. 78; (2014); p. 35 – 42;,
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