Reacción #632005

Ecuación de reacción

tert-Butylamine

3-chloropropanesulfonyl chloride

→

desired product

Rendimiento 99.0%

N-tert-butyl-(3-chloro)propylsulfonamide

Rendimiento 99.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture was warmed to room temperature
2. 2
   FiltraciónThe mixture was filtered
3. 3
   Concentraciónthe filtrate was concentrated in vacuo
4. 4
   workup.DISSOLUTIONThe concentrate was dissolved in dichloromethane (2.0 L)
5. 5
   Lavadowashed with 1N HCl (1.0 L), water (1.0 L), brine (1.0 L)
6. 6
   Secadodried over Na2SO4
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated in vacuo
9. 9
   Otroto give a slightly yellow solid, which
10. 10
    Otrowas crystallized from hexane

Procedimiento

tert-Butylamine (3.0 mol, 315.3 mL) was dissolved in THF (2.5 L). The solution was cooled to −20° C. and treated slowly with 3-chloropropanesulfonyl chloride (1.5 mol, 182.4 mL). The reaction mixture was warmed to room temperature and stirred for 24 hours. The mixture was filtered, and the filtrate was concentrated in vacuo. The concentrate was dissolved in dichloromethane (2.0 L), washed with 1N HCl (1.0 L), water (1.0 L), brine (1.0 L), dried over Na2SO4, filtered, and concentrated in vacuo to give a slightly yellow solid, which was crystallized from hexane to provide the desired product as a white solid (316.0 g, 99%). 1H NMR (CDCl3) δ 1.38 (s, 9H), 2.30-2.27 (m, 2H), 3.22 (t, J=7.35 Hz, 2H), 3.68 (t, J=6.2 Hz, 2H), 4.35 (br, 1H).

Fuente