Reference of 33786-89-9,Some common heterocyclic compound, 33786-89-9, name is 5-Chloro-m-phenylenediamine, molecular formula is C6H7ClN2, 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.
STR4 Using the above description one ordinarily skilled in the art can make and use the compounds of this invention. Specific embodiments of the invention are provided below. Structures and names of the embodied compounds are found summarized in CHART C. The examples below serve to illustrate the invention and are not intended to limit the invention in any manner. Example 1. Synthesis of N-(3-azido-5-ehlorophenyl)-N’-cyano-N”-(1,1dimethylpropyl)guanidine. Chart A. Step A-2. A stirred solution of 5-chloro-1,3-phenylenediamine (A-1, X is Cl, 1.93 g, 13.5 mmol) in 55 mL of dichloromethane is cooled to 0 C. and di-tert-butyl dicarbonate (2.96 g, 13.5 mmol) is added. The reaction mixture is stirred at 20-25 C. for 5 days and then concentrated. The residue is purified by medium pressure liquid chromatography using 25% ethyl acetate in hexane to afford 2.20 g of 3-amino-5-chlorophenylcarbamic acid, 1,1-dimethylethyl ester. (A-2) mp 85-87 C.; IR (mull) 3439, 3357, 3328, 2926, 1691, 1613, 1589, 1524, 1475, 1438, 1391, 1366, 1311, 1274, 1240, 1159, 851 cm-1; 1 H NMR (CDCl3) delta6.77 (bs, 1 H), 6.64 (m, 1 H), 6.39 (bs, 1 H), 6.34 (m, 1 H), 3.73 (bs, 2 H), 1.50 (s, 9 H); 13 C NMR (CDCl3) delta152.1, 147.8, 139.9, 134.8, 109.4, 108.2, 102.6, 80.5, 28.2; Analysis calculated for C11 H15 CIN2 O2: C, 54.44; H, 6.23; N, 11.54; Cl, 14.61. Found: C, 54.27; H, 6.50; N, 10.96; Cl, 13.99.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Chloro-m-phenylenediamine, its application will become more common.
Reference:
Patent; The Upjohn Company; US5525742; (1996); A;,
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