反応 #2374974

反応方程式

p-toluenesulfonyl chloride

1,5,9-triazanonane

→

crude product

収率 59.0%

1,5,9-Tris(p-toluenesulfonyl)-1,5,9-triazanonane

収率 59.0%

溶媒

pyridine

pyridine

反応条件

後処理

1. 1
   温度maintaining the temperature ≤60° C
2. 2
   workup.ADDITIONThe addition required 15 minutes
3. 3
   その他The solvent was removed in vacuo
4. 4
   workup.DISSOLUTIONthe resulting yellow oil was dissolved in ethyl acetate (1 l)
5. 5
   その他The ethyl acetate layer was separated
6. 6
   洗浄washed with 0.1 N HCl, H2O and saturated NaCl solution
7. 7
   その他dried (MgSo4)
8. 8
   その他the solvent was removed in vacuo

実験手順

To a stirred solution of p-toluenesulfonyl chloride (240 g, 1.26 mole) in pyridine (600 ml) at 0° C. was added a solution of 1,5,9-triazanonane (50.0 g, 0.381 mole) in pyridine (100 ml) under a dry nitrogen atmosphere, maintaining the temperature ≤60° C. The addition required 15 minutes. The solvent was removed in vacuo and the resulting yellow oil was dissolved in ethyl acetate (1 l) and H2O (500 ml). The ethyl acetate layer was separated, washed with 0.1 N HCl, H2O and saturated NaCl solution and dried (MgSo4). The solution was decolorized with silica gel and the solvent was removed in vacuo to give 133 g (59% yield) of the crude product as a glassy solid: 1H NMR (CDCl3) δ 1.71 (quint, J=6.6 Hz, 4 H), 2.42 (s, 6 H), 2.43 (s, 3 H), 2.96 (quart, J=6.4 Hz, 4 H), 3.11 (t, J=6.8 Hz, 4 H), 5.12 (t, J=6.6 Hz, 2 H), 7.30 (m, 6 H), 7.63 (m, 2 H), 7.73 (m, 4 H).

出典