Reaction #1884962

Reaction equation

tert-Butylamine

3-Chloropropanesulfonyl chloride

→

product

Yield 99.0%

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

Yield 99.0%

Solvents

THF

Conditions

Workup

1. 1
   TemperatureThe solution was cooled to −200C
2. 2
   FiltrationThe mixture was filtered
3. 3
   Concentrationthe filtrate was concentrated in vacuo
4. 4
   workup.DISSOLUTIONThe residue was dissolved in CH2Cl2 (2.0 L)
5. 5
   WashThe resulting solution was washed with 1 N HCl (1.0 L), water (1.0 L), brine (1.0 L)
6. 6
   Dryingdried over Na2SO4
7. 7
   FiltrationIt was filtered
8. 8
   Concentrationconcentrated in vacuo
9. 9
   Otherto give a slightly yellow solid, which
10. 10
    Otherwas crystallized from hexane

Procedure

tert-Butylamine (3.0 mol, 315.3 mL) was dissolved in THF (2.5 L). The solution was cooled to −200C. 3-Chloropropanesulfonyl chloride (1.5 mol, 182.4 mL) was added slowly. The reaction mixture was allowed to warm to rt and stirred for 24 h. The mixture was filtered, and the filtrate was concentrated in vacuo. The residue was dissolved in CH2Cl2 (2.0 L). The resulting solution was washed with 1 N HCl (1.0 L), water (1.0 L), brine (1.0 L) and dried over Na2SO4. It was filtered and concentrated in vacuo to give a slightly yellow solid, which was crystallized from hexane to afford the product as a white solid (316.0 g, 99%).

Source