Réaction #632005

Équation de réaction

tert-Butylamine

3-chloropropanesulfonyl chloride

→

desired product

Rendement 99.0%

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

Rendement 99.0%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction mixture was warmed to room temperature
2. 2
   FiltrationThe mixture was filtered
3. 3
   Concentrationthe filtrate was concentrated in vacuo
4. 4
   workup.DISSOLUTIONThe concentrate was dissolved in dichloromethane (2.0 L)
5. 5
   Lavagewashed with 1N HCl (1.0 L), water (1.0 L), brine (1.0 L)
6. 6
   Séchagedried over Na2SO4
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated in vacuo
9. 9
   Autreto give a slightly yellow solid, which
10. 10
    Autrewas crystallized from hexane

Mode opératoire

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).

Source