Reaktion #632005

Reaktionsgleichung

tert-Butylamine

3-chloropropanesulfonyl chloride

→

desired product

Ausbeute 99.0%

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

Ausbeute 99.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was warmed to room temperature
2. 2
   FiltrationThe mixture was filtered
3. 3
   Einengenthe filtrate was concentrated in vacuo
4. 4
   workup.DISSOLUTIONThe concentrate was dissolved in dichloromethane (2.0 L)
5. 5
   Waschenwashed with 1N HCl (1.0 L), water (1.0 L), brine (1.0 L)
6. 6
   Trocknendried over Na2SO4
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated in vacuo
9. 9
   Sonstigeto give a slightly yellow solid, which
10. 10
    Sonstigewas crystallized from hexane

Vorschrift

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).

Quelle