Reacción #324356

ord-ea36cede2a55439582f41fdf9e0414d9

Ecuación de reacción

Nc1ccccc1
aniline
CCN(C(C)C)C(C)C
N,N-diisopropylethylamine
O=S1(=O)CCCO1
propane sultone
CC[NH+](C(C)C)C(C)C.CC[NH+](C(C)C)C(C)C.O=S(=O)([O-])CCCN(CCCS(=O)(=O)[O-])c1ccccc1
di[ethyl(diisopropyl)ammonium] 3-(3-sulfonatopropylanilino)-1-propanesulfonate
Rendimiento 94.0%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe solvent was evaporated
  2. 2
    workup.ADDITIONethylacetate was added
  3. 3
    FiltraciónThe precipitated DIPEA bromide was filtered off
  4. 4
    Otrothe filtrate was evaporated
  5. 5
    workup.ADDITIONThe residue was treated with ether

Procedimiento

A mixture of aniline (7 mmol), N,N-diisopropylethylamine (DIPEA, 18 mmol) and propane sultone (16 mmol) was heated in a pressure tube in 10 mL of acetonitrile at 120-130° C. for 9 h under argon atmosphere. The solvent was evaporated and ethylacetate was added. The precipitated DIPEA bromide was filtered off and the filtrate was evaporated. The residue was treated with ether to give di[ethyl(diisopropyl)ammonium] 3-(3-sulfonatopropylanilino)-1-propanesulfonate as a white or pinky-white solid. Yield: 94%.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08642014B2uspto-grants-2014_02