反应详情

温度

60 °C

A solution of 2-bromoethanesulfonic acid, sodium salt (4.2 g, 20 mmol) in water (total 12 mL) was added over 6 hours to a 42° C. solution of t-butylamine (10 mL, 94 mmol) in a mixture of water (10 mL) and 1,4-dioxane (10 mL). The mixture was stirred at 42° for 18 hours. The mixture was then heated to 60° C. for 24 h. By proton NMR, 30% of elimination product (vinylsulfonic acid) was observed. The mixture was concentrated to dryness and treated with ethanol at refluxing temperature. The solid material was collected (crop 1). The mother liquor was concentrated to dryness and the solid was again treated with ethanol at refluxing temperature, and the solid material was collected (crop 2). Both crops of the solid material were dissolved in water, and the resultant aqueous solutions passed in sequence through a Dowex 50 W X 8 ion-exchange column (100 g resin). The fractions containing the title compound were collected and concentrated to dryness. The solid material obtained was recrystallized from a mixture of ethanol (20 mL) and water (2 mL). The crystals were collected by filtration, dried in a vacuum oven at 60° C. for 18 hours. Compound DU was obtained as fine white needles (860 mg, 24% yield). 1H NMR (500 MHz, D2O) δ 1.16 (s, 9H), 3.02 (t, J=6.8 Hz, 2H), 3.19 (t, J=6.8 Hz, 2H). 13C NMR (125 MHz, D2O) δ 24.8, 37.3, 47.0, 57.8. ES-MS 182 (M+1)

1. concentrationThe mixture was concentrated to dryness
2. additiontreated with ethanol
3. temperatureat refluxing temperature
4. customThe solid material was collected (crop 1)
5. concentrationThe mother liquor was concentrated to dryness
6. additionthe solid was again treated with ethanol
7. temperatureat refluxing temperature
8. customthe solid material was collected (crop 2)
9. dissolutionBoth crops of the solid material were dissolved in water
10. additionThe fractions containing the title compound
11. customwere collected
12. concentrationconcentrated to dryness
13. customThe solid material obtained
14. customwas recrystallized from a mixture of ethanol (20 mL) and water (2 mL)
15. filtrationThe crystals were collected by filtration
16. customdried in a vacuum oven at 60° C. for 18 hours