反应详情

Step B-2. To a stirred suspension of N-(3-azido-5-chlorophenyl)-N'-cyanocarbamimidic acid, phenyl ester (B-1, 0.705 g, 2.25 mmol) in 10 mL of isopropanol is added tert-amylamine (1.0 mL, 9.02 mmol). The reaction mixture is heated at reflux for 4 hours, cooled and concentrated. The organic residue is purified by flash chromatography using 30% ethyl acetate in hexane as the eluent to afford 0.45 g of N-(3-azido-5-chlorophenyl)-N'-cyano-N"-(1,1-dimethylpropyl)guanidine. (B-2) Mp 147°-149° C.; IR (mull) 3325, 3234, 2925, 2159, 2121, 2108, 1611, 1595, 1578, 1558, 1495, 1414, 1228, 853 cm-1 ; 1H NMR (DMSO) δ7.10 (bs, 1 H), 6.80 (m, 1 H), 6.74 (m, 1 H), 6.65 (m, 1 H), 1.55 (q, 2 H, J=7 Hz), 1.14 (s, 6 H), 0.68(t, 3 H, J=7 Hz).; 13 C NMR (DMSO) δ156.3, 141.8, 141.7, 134.5, 116.5, 116.2, 113.4, 109.2, 54.7, 32.3, 26.1, 8.4; Melt Solvate: 0.63% Chloroform; Analysis calculated for C13H16ClN7 plus 0.63% CHCl3 :C, 50.81; H, 5.23; N, 31.86; Cl, 12.08. Found: C, 50.73; H, 5.15; N, 31.57; Cl, 12.35.

1. temperatureThe reaction mixture is heated
2. temperatureat reflux for 4 hours
3. temperaturecooled
4. concentrationconcentrated
5. customThe organic residue is purified by flash chromatography