反应 #326981

反应方程式

acetone

octylamine

1,4-butane sultone

→

4-(octylamino)-1-butanesulfonic acid

收率 31.0%

溶剂

tetrahydrofuran

反应条件

后处理

1. 1
   温度The solution was heated
2. 2
   温度to reflux for 5 hours
3. 3
   其他The product formed a gel
4. 4
   workup.DISSOLUTIONto dissolve the product
5. 5
   其他a white solid precipitated
6. 6
   过滤The solid was collected by filtration
7. 7
   其他dried in vacuo
8. 8
   workup.DISSOLUTIONThe product was dissolved in EtOH
9. 9
   洗涤Dowex 50×8 resin (pre-washed, 6 g)
10. 10
    workup.ADDITIONwas added to the solution
11. 11
    过滤the resin was filtered
12. 12
    其他The filtrate was evaporated under educed pressure
13. 13
    其他the product was dried in vacuo

实验过程

To a solution of octylamine (2.20 g, 17.0 mmol) in tetrahydrofuran (11 mL) was added 1,4-butane sultone (2.30 g, 16.2 mmol). The solution was heated to reflux for 5 hours. The reaction was cooled to room temperature. The product formed a gel. A few drops of EtOH were added to dissolve the product. The solution was poured in a large excess of acetone (25 mL). After 5 minutes, a white solid precipitated. The solid was collected by filtration and dried in vacuo. The product was dissolved in EtOH and Dowex 50×8 resin (pre-washed, 6 g) was added to the solution. The suspension was stirred for 15 minutes and the resin was filtered. The filtrate was evaporated under educed pressure and the product was dried in vacuo. Yield: 31%. 1H NMR (DMSO, 500 MHz) δ ppm 8.24 (s (broad), 1H), 2.85 (m, 4H), 2.45 (m, 2H), 1.64 (m, 4H), 1.61 (m, 2H), 1.25 (m, 10H), (m, 2H), 0.85 (t, 3H, J=6.8 Hz). 13C (DMSO, 125 MHz) δ ppm 51.22, 47.54, 47.38, 31.82, 29.14, 26.59, 26.13, 25.51, 22.95, 22.75, 14.64. ES-MS 266 (M+1).

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