Reacción #1884962

ord-898e242162d8486fb5e3eaee4ead7238

Ecuación de reacción

CC(C)(C)N
tert-Butylamine
O=S(=O)(Cl)CCCCl
3-Chloropropanesulfonyl chloride
CC(C)(C)NS(=O)(=O)CCCCl
product
Rendimiento 99.0%
CC(C)(C)NS(=O)(=O)CCCCl
N-tert-Butyl-(3-chloro)propylsulfonamide
Rendimiento 99.0%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    TemperaturaThe solution was cooled to −200C
  2. 2
    FiltraciónThe mixture was filtered
  3. 3
    Concentraciónthe filtrate was concentrated in vacuo
  4. 4
    workup.DISSOLUTIONThe residue was dissolved in CH2Cl2 (2.0 L)
  5. 5
    LavadoThe resulting solution was washed with 1 N HCl (1.0 L), water (1.0 L), brine (1.0 L)
  6. 6
    Secadodried over Na2SO4
  7. 7
    FiltraciónIt was filtered
  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 −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%).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08343477B2uspto-grants-2013_01