Synthetic Route of 121-30-2, These common heterocyclic compound, 121-30-2, name is 4-Amino-6-chlorobenzene-1,3-disulfonamide, 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.
To a solution of aminoacetaldehyde dimethylacetal (2.18 mL, 2.13 g, 20.2 mmol) in EtOAc (25 mL) at 0 C. was added dropwise a solution of HCl in ether (13 mL, 2N solution in ether). The mixture was stirred at 0 C. for 5 minutes. To this solution, 4-chloro-6-aminobenzene-1,3-disulfonamide (Aldrich, 5.8 g, 20.3 mmol) in diethylene glycol dimethylether (30 mL) was added. The reaction mixture was then heated at 60-90 C. for 1 hour. The solvent was decanted and the solid was dissolved in water. An aqueous solution of Na2CO3 (10%) was added to adjust the pH 7-8, extracted with EtOAc, dried over Na2SO4, filtered and the solvent was evaporated. The crude material was chromatographed on silica gel eluting with CH2Cl2:EtOAc:MeOH (1:1:0.2 to 1:1:1) to give the title compound (3 g, 53% yield) as a white solid: mp 157-160 C. 1H NMR (400 MHz, d6-DMSO) delta 7.97 (s, 1H), 7.05 (s, 1H), 5.65-4.70 (m, 1H), 2.88-2.96 (m, 1H), 2.77-2.84 (m, 1H); 13C NMR (100 MHz, d6-DMSO) delta 147.1, 134.8, 128.4, 125.9, 118.7, 117.6, 68.1, 44.9. Mass spectrum (API-TIS) m/z 325 (M-H), 327 (MH+); Anal. calcd for C8H11ClN4O4S20: C, 30.06; H, 3.54; N, 16.70. Found: C, 30.26; H, 3.40; N, 16.38.
Statistics shows that 4-Amino-6-chlorobenzene-1,3-disulfonamide is playing an increasingly important role. we look forward to future research findings about 121-30-2.
Reference:
Patent; NitroMed, Inc.; US2006/189603; (2006); A1;,
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